Choptank River Rentals
- From $295 per night (USD)
VRBO
Cozy Home in Historic West End Perfect for Ironman
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy your getaway in historic Cambridge in our spacious & serene home. Located in the Historic West End, the home comf ...
From $295 per night (USD)VRBO
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Expedia
Your “Happy Place”-Updated beautifully 3 story home on quiet island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
An amazing escape on the Chesapeake Bay. Explore Tilghman Island by bike or boat. Enjoy fresh seafood from the local se ...
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VRBO
Casual Bungalow close to Choptank River, sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A newly renovated pristine bungalow close to downtown Cambridge, MD. We are conveniently located near St. Michael, East ...
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Expedia
Charmer Base for Eastern Shore Exploration
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful Vintage Farm House apartment located right in the mid of the Eastern Shore Peninsular, with its unique lo ...
Click For PricingExpedia
- From $333 per night (USD)
VRBO
A little slice of heaven on the Choptank River
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A perfect getaway on our waterfront property .You will have your own private beach. You can enjoy crabbing ,fishing , ka ...
From $333 per night (USD)VRBO
- From $346 per night (USD)
VRBO
New Waterfront! Drop Anchor on Brannocks Bay. An Amazing waterfront retreat!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Take it easy at this unique and tranquil getaway located on the Choptank River with oceanliner views of the Chesapeake B ...
From $346 per night (USD)VRBO
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VRBO
Historic Farmhouse on the Chesapeake Bay! PANORAMIC Waterfront Sunsets. 🌅
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Beautifully Restored 1925 HISTORIC FARMHOUSE with panoramic waterfront views. New roof, new flooring, new furniture, new ...
Click For PricingVRBO
- From $317 per night (USD)
Expedia
Minutes from Downtown St. Michaels and Tilghman | Newly Renovated | Kayaks | Cha
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Eastern Shore Vacation Rentals presents Banyan Cottage. This impressive and simply idyllic 2BR/2BA vacation cottage is t ...
From $317 per night (USD)Expedia
- From $299 per night (USD)
VRBO
New listing! Riverside Retreat on the Choptank River
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview renta ...
From $299 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Bright, rustic, waterfront farmhouse retreat resting on over 9 acres. The water views can be enjoyed almost anywhere fro ...
From $550 per night (USD)VRBO
- From $499 per night (USD)
VRBO
Magnificent Historic Home by Water is Ready!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Our house, built in 1736, is ideally located in the heart of historic Cambridge. Facing the Choptank River, it is 1/2 bl ...
From $499 per night (USD)VRBO
- From $319 per night (USD)
VRBO
Beautiful Waterfront Retreat in Cambridge!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Spend your day crabbing and fishing off our new dock or simply sip your coffee or cocktails as you watch the sunrises an ...
From $319 per night (USD)VRBO
- From $202 per night (USD)
VRBO
Modern Cambridge Cottage: Walk to Town, Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Pairing modern comforts with timeless charm, this 1-bath studio offers an ideal stay on your next visit to coastal Cambr ...
From $202 per night (USD)VRBO
- From $235 per night (USD)
VRBO
Newly Remodeled Home, 10 Minute Walk to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect for Eagleman and Ironman weekends! Backs to bike course on Glasgow! 3 Blocks From Historic Downtown! The whole ...
From $235 per night (USD)VRBO
- From $434 per night (USD)
VRBO
Cozy Cambridge Retreat w\/ Casita Near Marina!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Your next family retreat awaits at this 4-bedroom, 3-bath home featuring a spacious casita! With its central location, t ...
From $434 per night (USD)VRBO
- From $893 per night (USD)
VRBO
Waterfront Estate w\/ Stunning Views, Deepwater Dock, Pool, HotTub, Kayaks & More
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This 4500+ sq feet waterfront estate, located just off of the Choptank River offers stunning water views from nearly eve ...
From $893 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Luxury on the river, steps to downtown &boat ramp!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beautifully crafted 1915 Sailmakers home nestled perfectly off the choptank harbor. Newly renovated with stunning appoin ...
From $299 per night (USD)VRBO
- From $437 per night (USD)
Expedia
Downtown Cambridge | Historic Charm | Modern Upgrades
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect location for an easy getaway in any season! Overlooking Cambridge's stunning marina and yacht club, this im ...
From $437 per night (USD)Expedia
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VRBO
A Kozy Waterfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
About this space From the balcony of this Kozy Waterfront Condo, enjoy relaxing sunsets overlooking the marina, and a bi ...
Click For PricingVRBO
- From $358 per night (USD)
Expedia
Minutes from Downtown Cambridge | Private Dock | Kayaks | Bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This gorgeous 2-bedroom , 2-bathroom cottage waterfront was designed with your comfort in mind. Your search for the fin ...
From $358 per night (USD)Expedia
- From $238 per night (USD)
VRBO
The Crabby Little Oyster Cottage in Cambridge MD
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Crabby Little Oyster Cottage offers incomparable peace and quiet and convenience. This home has some special touches ...
From $238 per night (USD)VRBO
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VRBO
NEW Listing WATERFRONT sleeps 10 5 bedrooms 4 1\/2 bths - dock & pool STN-23-23
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
STN-23-23 - First time offered waterfront located on Boone Creek between Oxford and Easton. Home features 5 bedrooms - ...
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- From $378 per night (USD)
VRBO
New private waterfront Eastern shore home w\/ pier + peaceful water views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Peaceful Point! Come enjoy the beauty of the water and the serenity it brings at Peaceful Point. This perfe ...
From $378 per night (USD)VRBO
- From $203 per night (USD)
VRBO
Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our charming 3-bedroom Midcentury modern home in Cambridge! This stunning home boasts a retro vibe with uniqu ...
From $203 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Waterfront property with private boat ramp and new dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private Boat Ramp and Large New Pier on your property! Launch your own boat from the private boat ramp or enjoy our wa ...
From $225 per night (USD)VRBO
- From $350 per night (USD)
Expedia
High Water Guest House<br>
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of h ...
From $350 per night (USD)Expedia
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Expedia
Private Waterfront Cottage on Bolingbroke Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Totally Private, quiet water-front cottage with wood burning fireplace and exclusively private 60' Lap Pool(open mid-Apr ...
Click For PricingExpedia
- From $175 per night (USD)
Expedia
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy historic Cambridge all year at this fully stocked and freshly renovated 2 bedroom, 2.5 bath townhouse across the s ...
From $175 per night (USD)Expedia
- From $215 per night (USD)
VRBO
Fabulous SUMMER rates!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This newly built cottage is located in the quaint waterman's community of Tilghman Island. The perfect spot to ...
From $215 per night (USD)VRBO
- From $342 per night (USD)
VRBO
Family friendly with a Pool and Game Room. Convenient Location with a view.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Come stay at this centrally-located home with beautiful views of the Choptank River. Enjoy sun filled days by the custom ...
From $342 per night (USD)VRBO
- From $415 per night (USD)
VRBO
\"Point of View\" Waterfront cottage with panoramic views on Tilghman Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Tilghman Island “Point of View” is a waterfront property located on Tilghman Island, with a 270-degree water view ov ...
From $415 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Skipjack cottage an original watermen's home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: If you are looking for a peaceful & friendly area to getaway too, look no further. Once across the bridge you ...
From $295 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Honeymoon Special - fall in love again - Stay 3 nights get 4 free
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STRN-23-58 Renovated Watermans Cottage circa 1920. Wide water views and bay breezes! This fantastic 1920's Waterman's co ...
From $350 per night (USD)VRBO
- From $538 per night (USD)
Expedia
NEW LISTING! Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-217-FLU Welcome to your dream waterfront getaway just moments away from the charming town of St. Michaels. This met ...
From $538 per night (USD)Expedia
- From $245 per night (USD)
VRBO
Pet-Friendly Cambridge Home - Walk to River!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Retreat to Cambridge with your loved ones and book this 3-bedroom, 1.5-bath vacation rental, 'The Happy Heron!' This hom ...
From $245 per night (USD)VRBO
- From $285 per night (USD)
Expedia
Downtown Oxford | Outdoor Dining | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This bright and airy 3BR, 2BA cape cod vacation home in Oxford is designed with your comfort in mind. The free-flowing f ...
From $285 per night (USD)Expedia
- From $299 per night (USD)
VRBO
Beautiful Home in Historic Waterfront District, Walk to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
➤ Just 1 block from the water, this Spacious unique Historic Home has been Renovated & Beautifully Furnished for a comfo ...
From $299 per night (USD)VRBO
- From $1019 per night (USD)
VRBO
Scenic and private waterfront eastern shore home.
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 18
Welcome to "The Cove at Cambridge" in Cambridge, Maryland. It is located on a private 38-acre farm with over 1000 ft of ...
From $1019 per night (USD)VRBO
- From $275 per night (USD)
VRBO
House in quiet neighborhood, on the water, with large backyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Cambridge, this delightful house is a dream. With 2 tranquil bedrooms featuring 2 queen beds, guests will fee ...
From $275 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Charming 4 bedroom in Historic Cambridge\n\n
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy the old world charm of this home, built in 1894 in the historic district of the picturesque and diverse town of Ca ...
From $450 per night (USD)Expedia
- From $235 per night (USD)
VRBO
B&B - The Lawson
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This delightful bed & breakfast is the perfect home base for your visit. The property includes a small beach, Adirondack ...
From $235 per night (USD)VRBO
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Expedia
Upscale Condo in Historic Downtown Cambridge, Maryland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to this fully renovated historic condo nestled in the heart of downtown Cambridge, Maryland, with its fabulous d ...
Click For PricingExpedia
- From $900 per night (USD)
VRBO
Historic and Spacious Stewart House
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 12
The Stewart House is a large, beautiful 18 th century home in located the heart of the historic district of Cambridge on ...
From $900 per night (USD)VRBO
- From $197 per night (USD)
Expedia
Relaxation Haven on the Shore near Choptank River
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
No matter you're from a family long time no see for each other or a group of friends who miss your get togethers, Relaxa ...
From $197 per night (USD)Expedia
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VRBO
Beautiful Home in the Historic District w\/pool
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
This beautiful home in the Historic West End has so much to offer! Walking distance to all that Downtown Cambridge has ...
Click For PricingVRBO