Choptank River Rentals
From $216 per night (USD)VRBO
Station House West: 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 $216 per night (USD)VRBO
From $211 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 $211 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 $593 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 $593 per night (USD)Expedia
From $339 per night (USD)VRBO
Waterviews, Comfort & Convenience!
- Bedrooms:
- 2
- 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 $339 per night (USD)VRBO
From $308 per night (USD)Expedia
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 $308 per night (USD)Expedia
From $180 per night (USD)VRBO
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 $180 per night (USD)VRBO
From $490 per night (USD)Expedia
Waterfront Cambridge Home: Pool & Dock!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Find your slice of paradise at ‘Hudson Creek Retreat,’ a 4-bed, 4-bath Cambridge vacation rental. This family home offer ...
From $490 per night (USD)Expedia
From $537 per night (USD)VRBO
Riverfront Denton Estate on 7 Acres w/ Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Dog Friendly w/ Fee | Private Deck | Pool Table Spend your next Maryland getaway staying in style at a former Governor' ...
From $537 per night (USD)VRBO
From $306 per night (USD)VRBO
Pet-Friendly Island Getaway | Bikes & Porch
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience the best of Tilghman Island in this bright and inviting 3-bedroom, 2-bath cottage. Perfect for famil ...
From $306 per night (USD)VRBO
From $223 per night (USD)VRBO
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
- Bedrooms:
- 2
- 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 $223 per night (USD)VRBO
From $376 per night (USD)Expedia
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 $376 per night (USD)Expedia
From $857 per night (USD)VRBO
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 $857 per night (USD)VRBO
From $1095 per night (USD)Expedia
Ironman & Eagleman - 4-bedroom house in charming Cambridge.
- Bedrooms:
- 2
- 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 $1007 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 $1007 per night (USD)VRBO
From $2089 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 $2089 per night (USD)Expedia
From $174 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 $174 per night (USD)VRBO
From $871 per night (USD)VRBO
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,15%off 7day stay
- Bedrooms:
- 3
- 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 $871 per night (USD)VRBO
From $281 per night (USD)VRBO
Tilghman Island Retreat By Knapps Narrows!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Furnished Sunroom | Family Friendly | Half-Mi to Marina Make your way to this lovely Tilghman Island vacation rental, i ...
From $281 per night (USD)VRBO
From $860 per night (USD)VRBO
Stunning Waterfront Escape with New Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Whether you're looking to relax poolside or explore the surrounding area, this waterfront home has everything y ...
From $860 per night (USD)VRBO
From $443 per night (USD)VRBO
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Wake up to sweeping Chesapeake Bay views just minutes from St. Michaels. Cast a line from your private dock, si ...
From $443 per night (USD)VRBO
From $424 per night (USD)Expedia
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 $424 per night (USD)Expedia
From $1257 per night (USD)VRBO
Short drive to Downtown Cambridge | Private Dock | Guest House
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 14
Bucolic and Serene NEW POOL COMING SOON! This charming 6BR, 3BA Victorian waterfront vacation home complimented by a 1B ...
From $1257 per night (USD)VRBO
From $530 per night (USD)Expedia
Charming, waterfront 3-bedroom house in lovely Cambridge with AC, WiFi
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Get ready to relax by the water in this 3-bedroom house in Cambridge. This charming waterfront property features 2 king ...
From $530 per night (USD)Expedia
From $150 per night (USD)VRBO
Cambridge Apt in Walkable Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Waterfront Setting | Close to Local Eats Explore the quiet side of the Chesapeake Bay with your closest travel buddy at ...
From $150 per night (USD)VRBO
From $188 per night (USD)VRBO
Charming 1-bedroom cottage on the water, minutes from St Michaels MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
King Size Comfort. The ambience of each cottage is one of relaxed comfort. Fashionable cottage décor is enhanced with co ...
From $188 per night (USD)VRBO
From $247 per night (USD)VRBO
Waterfront cottage, 1 bd 1 bath, Perfect for your next getaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The perfect couples’ getaway. The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhan ...
From $247 per night (USD)VRBO
From $227 per night (USD)VRBO
Charming 2-bedroom cottage, waterfront, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect, small family, getaway. The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is ...
From $227 per night (USD)VRBO
From $422 per night (USD)VRBO
Walk to Dtwn: Waterfront Eastern Shore Townhome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Game Room | Scenic Waterfront Deck | Community Pool | Pet Friendly w/ Fee | EV Charger Experience life in the heart of ...
From $422 per night (USD)VRBO
From $935 per night (USD)Expedia
New! Chesapeake Bay Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Escape to this lovely 6-bedroom house and guest house on the Chesapeake Bay for a relaxing getaway. Amazing Freightliner ...
From $935 per night (USD)Expedia
From $270 per night (USD)VRBO
Aurora Blue - A Stylish Experience \n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stylish experience at the centrally located retreat. New owners purchased East and renovated the entire home both inside ...
From $270 per night (USD)VRBO
From $970 per night (USD)Expedia
Downtown Oxford | Private Beach | Private Pool | Luxury
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxury awaits at The Beach House, a stunning 4-bedroom, 4.5-bathroom vacation extravaganza in the vibrant Oxford neighbo ...
From $970 per night (USD)Expedia
From $1107 per night (USD)VRBO
Spacious 7-bedroom property with guest house, Wifi, AC in lovely Cambridge
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 6
Take it all in and relax at this beatiful Cambridge waterfront getaway on nearly five acres. It boasts a guest house wit ...
From $1107 per night (USD)VRBO
From $897 per night (USD)VRBO
Waterfront Retreat w Heated Salt Water Pool: Private Pier w Boat Docking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 15
Welcome to your perfect family getaway on Maryland’s Eastern Shore! Set on 4 peaceful acres along the river, our home is ...
From $897 per night (USD)VRBO
From $203 per night (USD)VRBO
Walk to Park & River: Dog-Friendly Cambridge Gem
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Half-Mi to Historic Downtown | Covered Porch | Yard Space | Great Fishing Area Whether you’re here to explore Cambridge ...
From $203 per night (USD)VRBO
From $289 per night (USD)Expedia
Walkable Condo w/ Drawbridge Views in Cambridge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Community Pool | Walk to Happy Hour at Portside | River-View Balcony Dive into waterfront serenity at this Cambridge va ...
From $289 per night (USD)Expedia
From $110 per night (USD)VRBO
Fabulous townhome in a safe community in Cambridge
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Located in Cambridge, enjoy what this 2-Bedroom + Office townhome has to offer. With 1 queen bed and kids bunk beds, gue ...
From $110 per night (USD)VRBO
From $970 per night (USD)VRBO
Waterfront Retreat w/Guest House&Heated Salt Water Pool: Pier w/ Boat Docking
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 15
Welcome to your perfect riverside escape! Nestled on 4 scenic acres along the river, our property offers a peaceful resp ...
From $970 per night (USD)VRBO
From $401 per night (USD)VRBO
Walk to Waterfront • Cozy Oxford Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Discover the charm of Maryland’s Eastern Shore at our cozy cottage nestled in the heart of Oxford. Just steps f ...
From $401 per night (USD)VRBO
From $975 per night (USD)Expedia
Waterfront Paradise | Pool, Views & Serenity
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Gather your favorite people and escape to a spacious waterfront haven in Royal Oak. From coffee at sunrise on ...
From $975 per night (USD)Expedia
From $141 per night (USD)VRBO
Station House East: Upscale Loft in the Historic District Cambridge, MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into style and comfort in this beautifully appointed 1-bedroom, 1.5-bath condo located in the iconic Four Corners ...
From $141 per night (USD)VRBO