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Middletown Holiday Rentals

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    Don't let other travellers get your favourite Middletown area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 20 Rentals in Middletown
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    The following rentals are within 40 kilometres of Middletown.
    Waldins waterfront house with amazing views - Top of the Chesapeake1 / 25
    (1)Excellent
    Charlestown, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Cozy & Spacious Chestertown Home1 / 28
    (5)Excellent
    Chestertown, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Chester River House with Views1 / 11
    (4)Very good
    Chestertown, MD
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Gorgeous Home on Chester River1 / 16
    (2)Very good
    Chestertown, MD
    4 Bedrooms, 9 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 February 2018
    This is a lovely , comfortable home. We enjoyed our stay very much and would definitely rent the house again. There were a few glitches due to the house having been closed up...
    Reviewed 7 June 2016
    Our group - kids and adults - thoroughly enjoyed our stay here. We loved being right on the water and enjoyed the beautiful view. The house was very clean and spacious. It was...
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    About this property
    This gorgeous home is located directly on the Chester River in Chestertown, Md, on the Eastern shore. There are 5 bedrooms, one down and four on the second floor. On the main floor there is a great room that is part kitchen, part TV area and part dining room. Off of this room is a lovely living...
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    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 9 Bathrooms, Sleeps 8
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    Wilmington
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Cable/satellite TV
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wilmington Masterpiece ! The Hamilton is a beautifully renovated and decorated home by Redefined Luxury Homes. Located in the heart of Historic Wilmington Delaware and just steps away from Trolley Square, Museum District and close to the Downtown riverfront area. Excellent for large groups. no pets...
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    Wilmington, Delaware 19806
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Belle Rose Cottage at Victory Farm (Pet Friendly!)1 / 17
    (3)Excellent
    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2018
    This is not my first stay at the cottage and I was stoked to be there. My wife and I had more than the space we needed as well as things we needed in the kitchen and laundry in...
    Reviewed 16 January 2018
    This cottage is a little piece of heaven. Everything you need for a short- or long-term stay is right at your fingertips: a full-sized kitchen, living room, bedroom, and a...
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    About this property
    Nestled behind the main house with a fenced garden, the cottage is a cozy respite after a busy day site seeing or visiting with local friends. Relax and discover the culture, history, nature, and cuisines of Maryland's Eastern Shore. Perfect for folks traveling with a dog or two. Short or long term...
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    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Wilmington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wilmington Masterpiece ! The Hamilton is a beautifully renovated and decorated home by Redefined Luxury Homes. Luxury Rooms Cool Spring / Trolley Square + Complimentary Coffee/Bagels + Spa like rooms, crisp linens, bottled water, WIFI + Walking distance to Trolley Square, Public Transport,...
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    Wilmington, Delaware 19806
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Retreat at a quiet, water front cottage1 / 14
    (3)Very good
    Chestertown, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2014
    If the unit is under construction, do not rent it. We should have been notified of the construction and given the opportunity to cancel.
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    About this property
    Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Still Pond, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Terrace
    • Patio
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
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    Still Pond, Maryland 21667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Washer
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cottage On Kent is a guest cottage within walking distance to downtown, the Chester River and Washington College. It has one bedroom with a queen size bed, a full kitchen, a spacious bathroom, a cozy living room, off-street parking and access to an outside sitting area. The Cottage is...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Sunview Cottage on Chesapeake Bay1 / 22
    (1)Excellent
    Chestertown, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Garden
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2015
    I took my mother here for a getaway birthday weekend. I wanted somewhere we could relax but also be inspired by our surroundings. This quaint cottage was perfect. Nestled close...
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    About this property
    Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from house and wraparound deck. Perfect destination for a couples getaway, family trip or friends gathering to enjoy the Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Peace and Quiet in a Delightful Victorian1 / 37
    (2)Very good
    Still Pond, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Private Garden
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2018
    Easy location, very lovely people who are kind and cordial. Perfect place to stay for a quick Eastern Shore visit.
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    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
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    Location Information
    Still Pond, Maryland 21667
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Charming Apartment in Historic Chestertown, MD1 / 10
    (7)Excellent
    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This is a lovely upstairs apartment with a super comfy bed, great shower, and everything you would want or need for an easy stay. The cupboards are stocked, you can cook if you...
    Reviewed 27 August 2015
    Absolutely the best deal for me in Chestertown. Came back to visit family and friends, and luckily this place was available. Home away from home, roomy, and I was able to work...
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    About this property
    This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An outdoor deck with cafe table and chairs is a nice place to sit on a sunny day. It is perfect for a...
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    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Elkton, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Washer
    • Housekeeping Included
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Children's Pool
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a cozy cute 1 person bedroom and this cozy 2 person bedroom in beautiful wooded setting, close to Fair Hill nature preserve, in Elkton, MD 21921. with shared bathroom, shared kitchen, laundry corner, sun room, pesticide free gardens and eco conscious woods. Short term or long term. Everybody...
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    Location Information
    Elkton, Maryland 21921
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This first floor apartment is cozy, sweet, and convenient to everything downtown. A quick 2 block walk brings you to restaurants, shops, galleries, the Farmer's Market on...
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    About this property
    A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point. Apartment accommodates 2 guests. It is the perfect place for enjoying this historic, artistic town on Maryland's Eastern Shore. The space includes kitchen/living room combo, bedroom with...
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    Location Information
    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Elkton, MD
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Secure Parking
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have 2 double bed rooms and a 1 person bedroom with shared bathroom, kitchen, sun room, deck, woods with bonfire, cob oven, yurt, outdoor bathroom, free roaming chickens, sheep, goat, cats, dogs, people, plants, gardens, fish pond, playground, bikes available, close to Fair Hill nature preserve,...
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    Location Information
    Elkton, Maryland 21921
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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    Pennsville, NJ
    6 Bedrooms, 5 Bathrooms, Sleeps 19 Quick View
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    • Balcony
    • Cable/satellite TV
    • Patio
    • Grill
    • Washer
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in rural Southern New Jersey, The Inn at M&M is unique, with a story dating to the 1600's. The Inn's scenic rural setting is ideal for your special occasion or private get-away. The Inn is equipped with modern bathrooms and all the amenities to make your stay enjoyable. This venue and...
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    Location Information
    Pennsville, New Jersey 08070
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 19
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    New Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the colonial roots of New Castle when you stay at this quaint 2-bedroom, 2-bathroom vacation rental house! Here, you'll find everything needed for a comfortable getaway including modern amenities like a open floor plan and fully equipped kitchen, with accommodations for 6 guests and...
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    Location Information
    New Castle, Delaware 19720
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Wilmington
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Available Two bedrooms in 3 BDR HOME. Full size Rooms. sleep two. Fully equipped KITCHEN. FRONT Porch and Fenced In Back Yard for privacy. DIRCT TV! NON Smoking professionals preferred. Tenant Must be able to care for home, responsible for recycling, Must care of Property in bad weather, keep...
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    Location Information
    Wilmington, Delaware 19804
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Hockessin
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * Please note that other renters live on site, in completely separate units, and may be present during your stay * Take a trip to the edge of Delaware and stay at this studio vacation rental apartment that sleeps 2 in Hockessin! You'll have the best of the northeast at your fingertips - with...
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    Location Information
    Hockessin, Delaware 19707
    Condo/Apartment - 1 Bathroom, Sleeps 2
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