Choptank River Rentals
From $375 per night (USD)VRBO
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 $375 per night (USD)VRBO
From $390 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 $390 per night (USD)Expedia
From $354 per night (USD)VRBO
Fall Weekends Await!
- 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 $354 per night (USD)VRBO
From $263 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 $263 per night (USD)VRBO
From $332 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 $332 per night (USD)VRBO
From $285 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 $285 per night (USD)VRBO
From $426 per night (USD)VRBO
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STRN-23-58 Simplicity Cottage is a circa 1920 Waterman's Cottage. Wide water views and bay breezes! This fantastic 1920' ...
From $426 per night (USD)VRBO
From $566 per night (USD)Expedia
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 $566 per night (USD)Expedia
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Pet-Friendly Cambridge Home - Walk to River!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Retreat to Cambridge with your loved ones and book this 3-bedroom, 1.5-bath vacation rental, 'The Happy Heron!' This hom ...
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From $446 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 $446 per night (USD)Expedia
From $222 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 $222 per night (USD)VRBO
From $1135 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 $1135 per night (USD)VRBO
From $449 per night (USD)VRBO
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 $449 per night (USD)VRBO
From $189 per night (USD)Expedia
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 $189 per night (USD)Expedia
From $349 per night (USD)VRBO
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 ...
From $349 per night (USD)VRBO
From $230 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 $230 per night (USD)Expedia
From $366 per night (USD)VRBO
Duck Cove Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR License - STRN-24-52 Come enjoy our charming, fully updated and renovated waterfront cottage located in the Eastern ...
From $366 per night (USD)VRBO
From $664 per night (USD)Expedia
WATERFRONT!! HOT TUB!! 4 BED\/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy this large peaceful Waterfront cabin-style home with your whole group! This beautifully updated home is super spac ...
From $664 per night (USD)Expedia
From $383 per night (USD)VRBO
Waterviews, Comfort & Convenience!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for some rest or relief…or perhaps just a little fun? This home is just steps away from the Cambridge Yacht Basi ...
From $383 per night (USD)VRBO
From $435 per night (USD)Expedia
Idyllic private waterfront location within walking distance to historic Oxford!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Sailor's Cottage allows you to get away from it all within walking distance of the charming and historic town of Oxford. ...
From $435 per night (USD)Expedia
From $469 per night (USD)VRBO
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Conductor's Rest, a fully renovated 2-bedroom historic condo nestled in the heart of downtown Cambridge, Mary ...
From $469 per night (USD)VRBO
From $1198 per night (USD)VRBO
The Wilder Way with a beautiful pool, hot tub, and a pickleball court!!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 23
If you’re looking for a place to go to relax with your family and friends look no farther! Surrounded by woodland and fi ...
From $1198 per night (USD)VRBO
From $127 per night (USD)VRBO
\nCozy retreat in peaceful wooded setting. Pet friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy peace and quiet in country setting where you can recharge your batteries. Small one room cottage with bathroom, ...
From $127 per night (USD)VRBO
From $158 per night (USD)Expedia
Hambrooks Home with Hottub\/ Mid Term stays welcomed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to my home of 2 beds, 2 baths, a large office so you can keep your nose to the grindstone if desired, and plenty ...
From $158 per night (USD)Expedia
From $485 per night (USD)VRBO
Waterfront Cambridge Home: Pool & Dock!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Find your slice of paradise at ‘Hudson Creek Retreat,’ a 4-bed, 5-bath Cambridge vacation rental. This family home offer ...
From $485 per night (USD)VRBO
From $507 per night (USD)Expedia
Riverfront Denton Estate on 7 Acres w\/ Fire Pit!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Dog Friendly w/ Fee | Private Dock | Pool Table Spend your next Maryland getaway staying in style at a former Governor' ...
From $507 per night (USD)Expedia
From $277 per night (USD)VRBO
Tranquil 3BR Retreat with BBQ & Bikes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Fishin Frank's Cottage on Tilghman Island Tucked away in the charming Watermans community of Tilghm ...
From $277 per night (USD)VRBO
From $190 per night (USD)Expedia
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Cambridge is waiting for you at this enchanting 4-bedroom house. Step inside and be greeted by the amazing decor that ex ...
From $190 per night (USD)Expedia
From $385 per night (USD)VRBO
The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Drinking Gourd...a freshly renovated 2-bedroom penthouse in the heart of the historic downtown district o ...
From $385 per night (USD)VRBO
From $640 per night (USD)Expedia
Minutes from Downtown Cambridge and Downtown Easton | 104+ Acre Farm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Farmhouse Surrounded by Nature This charming 4BR, 4BA vacation home with 104+/- acres on the Choptank River is the perf ...
From $640 per night (USD)Expedia
From $441 per night (USD)VRBO
Downtown Cambridge | Driveway Parking | Modern Upgrades
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Your Cambridge Hideaway With Driveway Parking Escape to a charming retreat where historic allure meets modern ...
From $441 per night (USD)VRBO
From $1095 per night (USD)Expedia
Ironman & Eagleman - 4-bedroom house in charming Cambridge.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This 4-bedroom house in Cambridge is perfect for your Eastern Shore experience. With 2 queen beds and 4 twin beds, guest ...
From $1095 per night (USD)Expedia
From $1052 per night (USD)VRBO
Gorgeous retreat across from yacht club, the Choptank, and IronMan finish line!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect location for an easy getaway in any season. The home is across the street from the IRONMAN Maryland finish l ...
From $1052 per night (USD)VRBO
From $2484 per night (USD)Expedia
\"Belle Aire Landing\" a Large Beautiful Waterfront Estate! Under New Management!
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 22
*Under New Management for 2025!* When thinking about an amazing vacation, the words that come to mind should be like 'A ...
From $2484 per night (USD)Expedia
From $235 per night (USD)VRBO
Sailwinds Loft at Cambridge Creek
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Waterview second story loft apartment in downtown Cambridge, MD with private entrance and secure bike storage! Located j ...
From $235 per night (USD)VRBO
From $832 per night (USD)VRBO
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to Juniper Cove! Large luxury waterfront home on 15 private acres, with a large in-ground salt water pool in Cam ...
From $832 per night (USD)VRBO
From $194 per night (USD)VRBO
Peaceful 2-Bedroom Estate for Monthly\/Bi-weekly Stay on Eastern Shore
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Difficult to find a temporary but comfortable transition place to live when moving? or you are a work-on-the-go, get rea ...
From $194 per night (USD)VRBO
From $237 per night (USD)Expedia
Tilghman Island Retreat By Knapps Narrows!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 4
Furnished Sunroom | Family Friendly | Half-Mi to Marina Make your way to this lovely Tilghman Island vacation rental, i ...
From $237 per night (USD)Expedia
From $540 per night (USD)VRBO
Stunning Waterfront Escape with New Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Whether you're looking to relax poolside or explore the surrounding area, this waterfront home has everything y ...
From $540 per night (USD)VRBO
From $392 per night (USD)Expedia
Holiday Cheer & Cozy Nights by the Fire
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Minutes from St Michaels, this peaceful retreat will have guests never wanting to leave. Panoramic views of the ...
From $392 per night (USD)Expedia
From $376 per night (USD)VRBO
Downtown Oxford | Outdoor Dining | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Old School Charm Meets New School Living! This charming 3BR, 2BA duplex vacation home within walking distance from Down ...
From $376 per night (USD)VRBO