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Cambridge Vacation Rentals

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    $565 Average
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    Travelers to Cambridge are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 15 Rentals in Cambridge
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    Waterfront Chespeake Bay Retreat1 / 27
    (11)Very good
    Cambridge
    7 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Stunning, Newer Chesapeake Waterfront Estate, Pool1 / 31
    (12)Very good
    Cambridge
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Cottage at Heron Cove, Chesapeake Bay, Cambridge1 / 39
    (8)Excellent
    Cambridge
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Fishing Cove on the Chesapeake Bay1 / 20
    (2)Excellent
    Cambridge
    8 Bedrooms, 6 Bathrooms, Sleeps 23 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 13, 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 December 5, 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...
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    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...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 23
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    Cambridge
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Parking
    • Cable/satellite TV
    • Terrace
    • Washer
    • Private Yard
    • 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...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cambridge
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    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...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Year Round Waterfront Prop. (Sleeps 18 )1 / 28
    (4)Excellent
    Cambridge
    5 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/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...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 18
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    Year Round Estate on Bay / Fam. Reunions / Slps 281 / 35
    (15)Excellent
    Cambridge
    7 Bedrooms, 7 Bathrooms, Sleeps 28 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Internet Access
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 30, 2016
    Lovely setting & a great location for sure. Nice big comfortable house. Great spot for big family reunion. This was our 2nd time we stayed here. Loved our first visit a...
    Reviewed August 3, 2012
    I would not change a single thing. Our family enjoyed the six day stay at this awesome place. The amenities were great, the location was central to other sights, and the...
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    About this property
    Captains Quarters on the Bay is a wonderful waterfront home with over 6,000+ Sq. Ft. of Living Space. Designer Appointed with All New Furnishings.7 Bedrooms with 6 Full Bathrooms, some with Jacuzzi/Whirlpool Baths. Gourmet Kitchen with Six Burner Stovetop and Triple Ovens. Large Game Room with...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 28
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    Cambridge
    21 Bedrooms, 15 Bathrooms, Sleeps 49 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This estate is privately situated on 22 acres of pristine and unspoiled Chesapeake waterfront property. It includes 5 homes, some being new to the rental market. Each have been painstakingly reconstructed and designer furnished in 2015, 2016 and 2017. The Spinnaker, Mariner and the Chart House each...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 21 Bedrooms, 15 Bathrooms, Sleeps 49
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    Cambridge
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    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...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    The following rentals are within 10 miles of Cambridge.
    Waterfront Vacation Home with Private Beach1 / 55
    (5)Average
    Trappe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Parking
    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 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 August 26, 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!
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    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...
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    Location Information
    Trappe, Talbot County 21673
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Yard
    • 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...
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    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Woolford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Yard
    • Cable/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...
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    Location Information
    Woolford, Maryland 21677
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Payment Protection
    Amenities & Details
    • Private Yard
    • 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...
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    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Payment Protection
    Amenities & Details
    • Private Yard
    • 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 Inquiry
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