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Holiday Rentals and Villas in Chester, MD and nearby

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    All 42 Rentals in the Chester Area
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    From
    £178
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    1 / 21
    5 of 5 stars (2) Excellent
    Chester
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
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    £239
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    1 / 37
    Chester
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    The following rentals are within 25 kilometres of Chester, Kent Island, Maryland.

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    £223
    / Night
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    1 / 25
    5 of 5 stars (3) Excellent
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    £159
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    1 / 26
    5 of 5 stars (1) Excellent
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Fireplace
    • DVD Player
    • Housekeeping...
    • Deck
    • Wi-Fi
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture, world-class restaurants & a vibrant, walkable capital city! Here in Upper Eastport, on a cul de sac, we are a short walk to the Historic Harbor & 3 blocks... View all property information
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    Location Information
    Annapolis, Maryland 21403
    5 of 5 stars Reviewed 16 July 2014
    If you want a cozy place to relax this is the place. Yard was perfect for my dog to run around and I did not have to worry it was all fenced in. Love to grill so I was able to...
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    £509
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    1 / 31
    5 of 5 stars (1) Excellent
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • DVD Player
    • Housekeeping...
    • Boat Available
    • Internet Access
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Bright, open, waterfront contemporary located on a landscaped property with magnificent views of Lake Ogleton! Pier (4'MLW) for your boat, crabbing, fishing and swimming. Bay Ridge Subdivison has great views, sandy beaches, streets for jogging, nature walks, and just great places to chill. Once... View all property information
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    Location Information
    Annapolis, Maryland 21036
    From
    £239
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    1 / 22
    5 of 5 stars (1) Excellent
    St. Michaels, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Watersports Nearby
    • Water Views
    • DVD Player
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and is fully-equipped and... View all property information
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    Location Information
    St. Michaels, Talbot County 21612
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    £318
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    1 / 18
    St. Michaels, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Watersports Nearby
    • Private Fishing...
    • Waterfront
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed... View all property information
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    Location Information
    St. Michaels, Talbot County 21653
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    £270
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    1 / 30
    4.5 of 5 stars (3) Very good
    Annapolis, MD
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Washer
    • Stereo System
    • Dryer
    • Satellite TV
    • Fireplace
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great care and paid pain-staking... View all property information
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    Location Information
    Annapolis, Maryland 21401
    4 of 5 stars Reviewed 21 June 2015
    Owner has everything imaginable in the home that you would ever need for a vacation getaway. The house has lots of room so you have your privacy when needed. Beautiful...
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    £159
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    1 / 17
    5 of 5 stars (3) Excellent
    Rock Hall, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Stereo System
    • Satellite TV
    • Washer
    • DVD Player
    • Patio
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s... View all property information
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    Location Information
    Rock Hall, Maryland 21661
    From
    £133
    / Night
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    1 / 11
    Stevensville
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave... View all property information
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    Location Information
    Stevensville, Kent Island 21666
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    £159
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    1 / 15
    4 of 5 stars (2) Very good
    Rock Hall, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented... View all property information
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    Location Information
    Rock Hall, Maryland 21661
    4 of 5 stars Reviewed 17 September 2014
    My sisters and mother stayed three nights in this quaint house with great views of one of the marina's and cove area. The downstairs was perfect my mother, with a screened in...
    4 of 5 stars Reviewed 19 August 2014
    My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no...
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    £115
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    1 / 12
    Rock Hall, MD
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and... View all property information
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    Location Information
    Rock Hall, Maryland 21661
    From
    £191
    / Night
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    1 / 9
    Annapolis, MD
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as... View all property information
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    Location Information
    Annapolis, Maryland 21401
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    £254
    / Night
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    1 / 22
    5 of 5 stars (1) Excellent
    Annapolis, MD
    3 Bedrooms / 6 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Water Views
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • TV
    • Ocean Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of... View all property information
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    Location Information
    Annapolis, Maryland 21409
    5 of 5 stars Reviewed 9 April 2015
    The home was located at a very continent location just 5-10mins drive to Naval academy and Annapolis downtown. The home was clean and have all the amenities. The water views from...
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    £477
    / Night
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    1 / 26
    5 of 5 stars (2) Excellent
    Annapolis, MD
    6 Bedrooms / 4 Bathrooms / Sleeps 13
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Game Room
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Deck
    • Pool Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms... View all property information
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    Location Information
    Annapolis, Maryland 21405
    5 of 5 stars Reviewed 28 September 2014
    Our large group of women in their 30's had a great time and everyone had a comfortable bed and plenty of room. Caitlyn was very responsive, friendly and accommodating from the...
    5 of 5 stars Reviewed 11 August 2014
    We just returned from our sailing weekend in Annapolis and had an amazing time staying at this lovely house for the weekend. The house was perfect for a larger group. The large...
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    £286
    / Night
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    1 / 13
    5 of 5 stars (6) Excellent
    St. Michaels, MD
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    • Satellite TV
    • Grill
    • Patio
    • Dryer
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful in town location! Just steps to shops, restaurants, winery, brewery, community pool, museums, boat ramp, and waterfront. This home has been renovated with amenities that will ensure a great time in St. Michaels. Home has three bedrooms; main floor master with a king and full bath,... View all property information
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    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed 13 June 2015
    We planned a girls weekend in St Michaels and rented this house for the weekend. It was so perfect! We couldn't have asked for more!! You can literally walk anywhere from here...
    5 of 5 stars Reviewed 10 September 2014
    The home was absolutely beautiful. Right around the corner from the town. Perfect location! We had been to St. Michaels 3 times before this trip and now we finally found our...
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    £127
    / Night
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    1 / 18
    Annapolis, MD
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Internet Access
    • Watersports Nearby
    • DVD Player
    • Air Conditioning
    • Deck
    • Water Park Nearby
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The perfect retreat for a family visiting Annapolis on vacation or for visiting your Johnny or Midshipman at the Naval Academy. This house is modestly priced yet has all the amenities and comfort of a home and the ability to eat in and cook your meals in our huge fully equipped kitchen or barbecue... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    £286
    / Night
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    1 / 7
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Water Views
    • Central Heating
    • Internet Access
    • Fireplace
    • Stereo System
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please... View all property information
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    Location Information
    Annapolis, Maryland 21401
    From
    £379
    / Night
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    1 / 26
    Annapolis, MD
    5 Bedrooms / 3 Bathrooms / Sleeps 20
    Overview Make Enquiry
    Amenities & Details
    • Playground
    • Shared Tennis Court
    • Hot Tub
    • Internet Access
    • Watersports Nearby
    • Air Conditioning
    • Private Fishing...
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    £286
    / Night
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    1 / 15
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Porch
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The house, built in 1878 by oyster packer Josiah Russell, has been owned by Campbell family members for at least four generations.On carpet, an elegant prayer rug is hung as a tapestry on a wall in the dining area. Chinese porcelain, cherished and collected by Jane and her parents, are displayed on... View all property information
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    Location Information
    Annapolis, Maryland 21401
    From
    £286
    / Night
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    1 / 23
    Annapolis, MD
    2 Bedrooms / 2 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Hot Tub
    • Water Views
    • Staffed Property
    • DVD Player
    • Satellite TV
    • Housekeeping...
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Eastport cottage sleeps 10 - 2 bedrooms with sleeping loft - 1 full and 1 half bath - 2 premium queen beds - 1 pull-out queen sleeper - 2 twins Unique Features - Walking distance to Naval Academy, downtown, shopping, restaurants and marinas - Shower for two - Off street parking for six -... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    £207
    / Night
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    1 / 6
    Annapolis, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our home is located in the Eastport section of Annapolis and just a short walk to Main street, the Historic District and the Naval Academy. We have a large back yard that's great for entertaining, plenty of off street parking and we're just across the street from the best view of the Chesapeake Bay... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    £223
    / Night
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    1 / 25
    5 of 5 stars (3) Excellent
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Fireplace
    • TV
    • Porch
    • Wi-Fi
    • Grill
    • Watersports Nearby
    • Air Conditioning
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around... View all property information
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    Location Information
    Annapolis, Maryland 21401
    5 of 5 stars Reviewed 23 April 2015
    beautiful cottage in a perfect location. 5 min walk to the Navy Stadium. 10 min walk to the historic downtown area where there are many specialty shops, restaurants, taverns and...
    5 of 5 stars Reviewed 15 April 2015
    I've used the "cottage" a few times on recommendation of a friend as I do business often in Annapolis and have found it to be convenient, comfortable and well cared for. With its...
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    £239
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    1 / 24
    Annapolis, MD
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Refrigerator
    • TV
    • Deck
    • DVD Player
    • Dryer
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    HOUSE This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    £414
    / Night
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    1 / 12
    Annapolis, MD
    1 Bedroom / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Terrace
    • Garage
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool...
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This beautiful and elegant 1 BR loft with 2.5 bath, that is nestled in a quiet but vibrant private residential community equipped with 2 swimming pools, 2 tennis courts and a restaurant, which sits on the water. This property is located in the Chesapeake Bay area. The security guard at the booth... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    £150
    / Night
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    1 / 9
    Rock Hall, MD
    3 Bedrooms / 1 Bathroom / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Patio
    • Refrigerator
    • Grill
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Charming 3 bed / 1 bath single family home with screened in front porch. Relax on the rocking chairs as you take in the charm of this lovely town on one of the prettiest streets in Rock Hall. Ample parking, large back yard with BBQ, tables and chairs to relax with family and friends after spending... View all property information
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    Location Information
    Rock Hall, Maryland 21661
    From
    £483
    / Night
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    1 / 38
    St. Michaels, MD
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Private Outdoor...
    • Water Views
    • Internet Access
    • Boat Available
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are... View all property information
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    Location Information
    St. Michaels, Talbot County 21663
    From
    £382
    / Night
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    1 / 14
    Annapolis, MD
    1 Bedroom / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Watersports Nearby
    • Ocean Views
    • Water Views
    • Swingset
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This beautiful and elegant 1 BR loft with 2.5 bath, that is nestled in a quiet but vibrant private residential community equipped with 2 swimming pools, 2 tennis courts and a restaurant, which sits on the water. This property is located in the Chesapeake Bay area. With access to the beach to the... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    £239
    / Night
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    1 / 9
    5 of 5 stars (1) Excellent
    Bozman, MD
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Water Views
    • Fireplace
    • Stereo System
    • Boat Available
    • Air Conditioning
    • Waterfront
    • Internet Access
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas... View all property information
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    Location Information
    Bozman, Talbot County 21612
    From
    £423
    / Night
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    1 / 7
    5 of 5 stars (9) Excellent
    Bozman, MD
    4 Bedrooms / 2 Bathrooms / Sleeps 13
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Deck
    • Internet Access
    • Boat Available
    • Air Conditioning
    • Washer
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch (2 queens, 1 double, daybed w/trundle, 5 twins) 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large... View all property information
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    Location Information
    Bozman, Talbot County 21612
    5 of 5 stars Reviewed 10 June 2015
    Perfectly situated on the water. The views are amazing, as is the pool. There is a huge lawn which is perfect for children of all ages. A short drive to St. Michael's, which is a...
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    From
    £159
    / Night
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    1 / 23
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Waterfront
    • Air Conditioning
    • Boat Available
    • DVD Player
    • Satellite TV
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Comfortable Timber Frame deep waterfront home in Annapolis close to USNA. Private wooded setting with wonderful water views. 3 miles to Annapolis Historic district. Easy commute to Washington, DC and Baltimore, MD. Tastefully furnished and equipped. View all property information
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    Location Information
    Annapolis, Maryland 21409
    From
    £124
    / Night
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    1 / 23
    5 of 5 stars (2) Excellent
    St. Michaels, MD
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • DVD Player
    • Fireplace
    • Water Views
    • Satellite TV
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor.... View all property information
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    Location Information
    St. Michaels, Talbot County NA
    5 of 5 stars Reviewed 29 May 2015
    I stayed at the Blades house last week and everything was just what we wanted. The location is beyond perfect (in walking distance of everything) and the house had all of the...
    5 of 5 stars Reviewed 19 August 2014
    Location location location! Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!
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    From
    £121
    / Night
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    1 / 29
    5 of 5 stars (12) Excellent
    St. Michaels, MD
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Water Views
    • Air Conditioning
    • Fireplace
    • Washer
    • Satellite TV
    • Waterfront
    • Internet Access
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor,... View all property information
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    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed 22 August 2014
    The pictures of this house do not lie. It is that nice. We parked our car and didn't need again until we left. Close to everything. Walk to the water , sit on the bench and...
    5 of 5 stars Reviewed 20 July 2014
    We fully enjoyed our relaxing stay in the sleepy little town of St. Michaels, and would definitely return when given the chance. The location is perfect - within a one block walk...
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    From
    £229
    / Night
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    1 / 32
    5 of 5 stars (6) Excellent
    St. Michaels, MD
    7 Bedrooms / 3 Bathrooms / Sleeps 11
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Internet Access
    • Stereo System
    • Waterfront
    • Fireplace
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and... View all property information
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    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed 15 June 2015
    My daughter was married in St. Michaels in May so I rented this house and filled it with family. It was a perfect "home base" for all of the activities surrounding the wedding...
    5 of 5 stars Reviewed 4 June 2015
    We loved this house and especially the location! Plenty of room for 11 of our friends! We loved the outside area and being right on the water! Walking distance to so many places...
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    From
    £159
    / Night
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    1 / 11
    4.5 of 5 stars (2) Very good
    Claiborne, MD
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Waterfront
    • Private Outdoor...
    • Internet Access
    • Stereo System
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake... View all property information
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    Location Information
    Claiborne, Talbot County 21663
    4 of 5 stars Reviewed 28 June 2015
    We were a group of two couples each with a young child. There was more than enough room for the 6 of us. The home is well located in Claiborne, about 5 min from downtown...
    5 of 5 stars Reviewed 11 October 2014
    Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and...
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    From
    £204
    / Night
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    1 / 17
    Annapolis, MD
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Patio
    • Internet Access
    • DVD Player
    • Deck
    • Air Conditioning
    • Satellite TV
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    2,700 Sq. Ft. Of Casual Waterfront Elegance 50' From The Chesapeake Bay ! 2,700 sq. ft. of casual waterfront elegance 50' from the shores of the Chesapeake bay and 15 minutes from historic downtown Annapolis and the Naval Academy... You will be so close to the Chesapeake Bay that your view from... View all property information
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    Location Information
    Annapolis, Maryland
    From
    £350
    / Night
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    1 / 23
    Stevensville
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Stereo System
    • Boat Available
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful 4 Bedroom, 4 Bath Quiet Waterfront Property, 3 queen bedrooms, 1 twin beds, 4 baths, two stories, fantastic master bedroom with mater bath complete with Roman soaking tub. Deck off of the master bedroom. Formal living room, Family room, Glass Sunroom, eat in kitchen, this spacious comes... View all property information
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    Location Information
    Stevensville, Kent Island 21666
    From
    £379
    / Night
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    1 / 24
    Annapolis, MD
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Washer
    • Satellite TV
    • Dryer
    • Internet Access
    • Waterfront
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of... View all property information
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    Location Information
    Annapolis, Maryland
    From
    £286
    / Night
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    1 / 13
    Annapolis, MD
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Internet Access
    • Dryer
    • DVD Player
    • Washer
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    NOTE: Please call me if you want to book my property. There have been security problems on all vacation rental sites. If anyone should ask you to wire funds please call me at the number listed on this site. Beautiful upgraded home in Eastport is perfectly located in small Cul De Sac... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    £286
    / Night
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    1 / 12
    Grasonville, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Boat Available
    • Air Conditioning
    • DVD Player
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 bath home offering a unique lodging to the discriminating traveler that other... View all property information
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    Location Information
    Grasonville, Maryland 21638
    From
    £178
    / Night
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    1 / 9
    St. Michaels, MD
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Stereo System
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Deck
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round... View all property information
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    Location Information
    St. Michaels, Talbot County 21662
    From
    £541
    / Night
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    1 / 24
    Annapolis, MD
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Stereo System
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. Check out this great video of the home and property: https://youtu.be/FBqOhPJZ-qU This incredible home has 100’ of floor-to-ceiling windows nestled in the tree canopy for expansive views of Weems Creek.... View all property information
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    Location Information
    Annapolis, Maryland 21401