Choptank River Rentals
From $366 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 $366 per night (USD)VRBO
From $422 per night (USD)Expedia
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
- Bedrooms:
- 1
- 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 $422 per night (USD)Expedia
From $785 per night (USD)VRBO
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 m ...
From $785 per night (USD)VRBO
From $549 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 $549 per night (USD)Expedia
From $393 per night (USD)VRBO
1915 Historic Cambridge Property w/ Fire Pit!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Experience the deep-rooted history of Cambridge when you book this 5-bedroom, 3.5-bathroom vacation rental. This ideally ...
From $393 per night (USD)VRBO
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The Yellow Victorian in Historic Cambridge – Walk to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
The best kept little secret! Historic Cambridge, less than 2hours from DC/VA and 1 hour to the beach. House is located j ...
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From $432 per night (USD)VRBO
Historic Renovated Jackrabbit Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make some memories at this unique and family-friendly 19th Century farmhouse. Relax, ride bikes a few short blocks to th ...
From $432 per night (USD)VRBO
From $385 per night (USD)VRBO
Family-Friendly Cambridge Home w/ Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape the hustle and bustle of your busy lives and retreat to this 3-bedroom, 2.5-bathroom vacation rental home! Along ...
From $385 per night (USD)VRBO
From $1708 per night (USD)VRBO
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 12
Looking to getaway, relax and recharge? This newly renovated coastal 7-bedroom, 6-bathroom waterfront getaway with a sp ...
From $1708 per night (USD)VRBO
From $640 per night (USD)Expedia
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Shorely, this is a true outdoor paradise! Originally a waterman's cottage, Neavitt Cottage has been tastefully updated ...
From $640 per night (USD)Expedia
From $430 per night (USD)VRBO
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your private escape on Tilghman Island — a waterfront home with panoramic water views, a dock for b ...
From $430 per night (USD)VRBO
From $966 per night (USD)Expedia
Breathtaking Waterfront Estate
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Durham-Hythe Estate is nestled within 7.5 acres of idyllic grounds with its own 750ft shoreline, 75ft private d ...
From $966 per night (USD)Expedia
From $907 per night (USD)VRBO
Waterfront Home on Chesapeake Bay with Dock, Bikes & Sunset Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to the quiet charm of Tilghman Island at this bright, open-concept waterfront home. Located directly on ...
From $907 per night (USD)VRBO
From $705 per night (USD)Expedia
Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore ...
From $705 per night (USD)Expedia
From $1206 per night (USD)VRBO
Scenic and private waterfront eastern shore home.
- Bedrooms:
- 3
- Bathrooms:
- 5
- 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 $1206 per night (USD)VRBO
From $104 per night (USD)VRBO
The Crabby Little Oyster Cottage in Cambridge MD
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Crabby Little Oyster Cottage offers incomparable peace and quiet and convenience. This home has some special touches ...
From $104 per night (USD)VRBO
From $254 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 $254 per night (USD)VRBO
From $1386 per night (USD)Expedia
Waterfront Home w/ Stunning Views, Deepwater Dock, Pool, HotTub, Kayaks & More
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to your private waterfront retreat in this 4,500 sq. ft. luxury home just off the Choptank River. Floor-to-ceilin ...
From $1386 per night (USD)Expedia
From $300 per night (USD)VRBO
Romantic Waterfront Cottage with Amazing Sunsets
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on the Chesapeake Bay side of Tilghman Island, our beautiful property is host to several cottages (one, two and ...
From $300 per night (USD)VRBO
From $671 per night (USD)Expedia
Private 9 acre Family Retreat on the Chesapeake Bay
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
This beautiful large home consists of 5 bedrooms, 4 bathrooms with stunning views of the Chesapeake. The home offers a l ...
From $671 per night (USD)Expedia