We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cambridge Holiday Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    £396 Average
    |||
    |||
    £0£1,000+
    Suitability
    More filters
    Travellers to Cambridge are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    All 29 Rentals in Cambridge
    Sort by:
    Default
    Stunning, Newer Chesapeake Waterfront Estate, Pool1 / 31
    (12)Very good
    Cambridge
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Year Round Estate on Bay / Fam. Reunions / Slps 281 / 35
    (15)Excellent
    Cambridge
    7 Bedrooms, 7 Bathrooms, Sleeps 28 Quick View
    Check in Check out
    Show Prices
    Cottage at Heron Cove, Chesapeake Bay, Cambridge1 / 39
    (8)Excellent
    Cambridge
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Fishing Cove on the Chesapeake Bay1 / 20
    (2)Excellent
    Cambridge
    8 Bedrooms, 6 Bathrooms, Sleeps 23 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Wi-Fi
    • Grill
    • Satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2016
    We had 14 people for thanksgiving..house had everything we needed! The kitchen was fully stocked with all the necessary cooking implements. And the 2 refrigerators were very...
    Reviewed 5 December 2016
    Our church group (11 men of all ages) had a most excellent weekend at this house and would be delighted to return some day. With only one person per bed, though, the max...
    See all reviews
    About this property
    Fishing cove is an 8 bedroom, 6 bath waterfront house tucked away in a lush pine forest that we rent on a monthly, weekly or weekend basis. Our waterfront vacation rental home on Maryland's Eastern Shore is on a very private cove with its own pier. The house is wheelchair accessible and the main...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 23
    Make Enquiry
    Perfect home for Ironman and Eagleman1 / 7
    (1)Excellent
    Cambridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Internet Access
    • Air Conditioning
    • Grill
    • Washer
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Cambridge
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Patio
    • Waterfront
    • Balcony
    • Washer
    • Grill
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From the hosts that have maintained a five star ratings on our cottage vacation rental, we would like to invite you to enjoy a special vacation in our four bedroom 3 full bath luxury estate home in the heart of the Chesapeake Bay. The house has just undergone a complete remodeling and...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier -  Sleeps 181 / 24
    (28)Excellent
    Cambridge
    5 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • DVD Player
    • Housekeeping Included
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 18
    Make Enquiry
    Waterfront Property with Pier1 / 18
    (16)Excellent
    Cambridge
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Satellite TV
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    6.5 Acre Waterfront Family Retreat with Pool and Sandy Beach!1 / 24
    (17)Excellent
    Cambridge
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • Washer
    • Grill
    • Satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    Cottage and or House on estate in Cambridge, MD1 / 21
    (37)Excellent
    Cambridge
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Save time - get the best Cambridge rentals sent straight to your email!
    Get the List
    Eastern Shore living at it's Best with 4 Bedrms, 2.5 baths and pool - sleeps 101 / 24
    (5)Excellent
    Cambridge
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Parking
    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    My Chesapeake Retreat Cambridge, Maryland1 / 23
    (11)Very good
    Cambridge
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • DVD Player
    • Internet Access
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Enquiry
    Large Luxury Townhouse with Elevator on Chesapeake Hyatt Property1 / 16
    (17)Excellent
    Cambridge
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • Balcony
    • Internet Access
    • Hot Tub
    • Shared Indoor Pool
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Waterfront Family Retreat with Deepwater Dock1 / 24
    (18)Excellent
    Cambridge
    4 Bedrooms, 2 Bathrooms, Sleeps 16 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Internet Access
    • Patio
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 16
    Make Enquiry
    Cedar Point Chesapeake Bay Waterfront Cottage1 / 21
    (5)Very good
    Cambridge
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming waterfront cottage on 6.5 private acres sits among swans and eagles on Marylands beautiful Eastern Shore. This professionally deorated cottage is packed with modern ammenities and charm. Saltwater Pool, Dock with seating, boat slip, water and electric; canoes and kayaks, woodburning...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    Cambridge
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Victorian Home In Historic West End1 / 24
    (9)Excellent
    Cambridge
    6 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Air Conditioning
    • Grill
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 13
    Make Enquiry
    Year Round Waterfront Prop. (Sleeps 18 )1 / 28
    (4)Excellent
    Cambridge
    5 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Satellite TV
    • Washer
    • Grill
    • Internet Access
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully designer furnished waterfront home is located in a very private setting overlooking the Chesapeake Bay and Little Choptank River. The property features magnificent water views, a private dock, fire pit, a large fenced swimming pool, large deck (partially covered), playground and...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 18
    Make Enquiry
    Family and Pet-Friendly, Waterfront with Pier1 / 24
    (49)Excellent
    Cambridge
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Parking
    • Washer
    • Internet Access
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Waterfront Retreat on the Little Choptank River...a private & secluded paradise!1 / 23
    (6)Very good
    Cambridge
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Cambridge
    5 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 13
    Make Enquiry
    Cambridge
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Balcony
    • Parking
    • Satellite TV
    • Terrace
    • Washer
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern home that has accommodations for more than 10+, with 2 full living room areas, 3 and half baths, Xfinity cable, with flat screen TVs in each of 5 bedrooms. Master with 50", mini fridge, sofa,loveseat, and ensuite master bath. Home is minutes away from some of the finest Eastern Shore Seafood...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    Cambridge
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Washer
    • Terrace
    • Parking
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the beautiful Eastern Shore of Maryland, Cambridge has been named one of the best ten small towns in the U.S. and is a boater's dream! The house has four private suites, full gourmet kitchen, three sitting areas, and two car garage. Check out the Dorchester County Tourism page for...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Enquiry
    Waterfront Chespeake Bay Retreat1 / 27
    (11)Very good
    Cambridge
    7 Bedrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 October 2014
    The Ideal Family VacationThis summer, our family decided to try something different and rent a house on the eastern shore of Maryland. After spending a day reconnoitering a...
    Reviewed 12 October 2014
    Really excellent location by the water, and the pool adds additional options. House itself is large, and is great for 2-3 families with kids. We were a group of friends, which...
    See all reviews
    About this property
    New premier waterfront vacation home - 6bed / 5bath home w/ beach & private pool. All of this on over 3 acres and +- 400 feet of stunning waterfront Near Cambridge Maryland, also Easton, St. Michaels and Oxford. The den also serves as an additional bdrm with full bath making it 7bdrms. Ideal...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 7 Bedrooms, Sleeps 18
    Make Enquiry
    The following rentals are within 15 kilometres of Cambridge.
    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Waterfront Vacation Home with Private Beach1 / 55
    (5)Average
    Trappe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Parking
    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2015
    We had a blast. The property, although the actual house could use a bit of updating, is GORGEOUS. We did notice that the home definitely housed a pet or two but did not smell...
    Reviewed 26 August 2014
    Beautiful home and view of the bay. Private beach was amazing. Perfect for a group of friends or a couple looking to get away. I will definitely be staying here again!
    See all reviews
    About this property
    Beautiful, serene waterfront home on the Chesapeake Bay. One hour from the Atlantic Ocean (Ocean City, Assateague Island) and Annapolis, One and a half hours from Washington DC and Baltimore. Many nearby places worth visiting, including picturesque St. Michaels and the Blackwater Wildlife Refuge...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Woolford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet Waterfront Retreat in Estate Setting - You will be staying in a charming, waterfront, 1-bedroom, carriage house located on a five-acre estate with surrounding tall pines and stately cedars. Your living quarters on the second floor, with private entrance and balcony, will overlook the pool and...
    View all property information
    Location Information
    Woolford, Maryland 21677
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property
    Owner log in