Dorchester Area Rentals
- From $533 per night (USD)
VRBO
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 15
This 4 bedroom 2 bath home is perfectly situated on a picturesque peninsula on Hudson Creek. There is a beautiful water ...
From $533 per night (USD)VRBO
- From $1092 per night (USD)
Expedia
Algonquin on the Choptank River is a great getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The house is on the Choptank River with awesome views, a pier with boat lift, great fishing and water activities. The h ...
From $1092 per night (USD)Expedia
- From $419 per night (USD)
VRBO
Beautiful Colonial Home on the Choptank River
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this newly updated 4-bedroom, 2-bath colonial home for a fun-filled retreat on the Cambridge coast! Offering k ...
From $419 per night (USD)VRBO
- From $220 per night (USD)
Expedia
Waterfront Getaway with Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bicyclist's and outdoorsman's dream! Neat little rancher on two waterfront acres just 4 miles from Blackwater Wildlife R ...
From $220 per night (USD)Expedia
- Click For Pricing
Expedia
Charming and Private with a Water view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This thoughtfully furnished, cozy 1 bedroom house is an ideal love nest or quiet retreat for writers, artists, nature lo ...
Click For PricingExpedia
- From $750 per night (USD)
Expedia
Indian Fields - 25-Acre Nature Lovers retreat!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 13
Indian Fields - Twenty-five acre nature lovers retreat! Pool, Kayaks, Fire Pit - The family Dog is Welcome! Bring your ...
From $750 per night (USD)Expedia
- From $270 per night (USD)
VRBO
Sunset Breezes - quiet waterfront retreat
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. G ...
From $270 per night (USD)VRBO
- From $595 per night (USD)
Expedia
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
We would like to welcome you to our charming getaway. This is the ideal spot for families, friends, or business retreats ...
From $595 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Cambridge Home w\/ Private Dock ~ 4 Mi to Dtwn
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Immerse yourself in the scenic views, maritime heritage, history, and art that Cambridge has to offer with a stay at thi ...
From $399 per night (USD)VRBO
- From $432 per night (USD)
Expedia
Tidal Serenity- Remote Waterfront Home with dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Two full houses one property. Perfectly set up for a multi-generational, authentic Eastern Shore vacation, Tidal Sereni ...
From $432 per night (USD)Expedia
- From $750 per night (USD)
VRBO
Waterfront Home, Large Property with Pool, Discount for Monthly\/Seasonal Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
This charming century old Eastern Shore farmhouse is situated on Brooks Creek in the heart of the Chesapeake Bay. It is ...
From $750 per night (USD)VRBO
- Click For Pricing
Expedia
Historic 1918 House 1\/2 Block from the Choptank River
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
This old fisherman's home in the historic district of Cambridge has been recently renovated and is close to restaurants, ...
Click For PricingExpedia
- From $270 per night (USD)
VRBO
Riverside Lodge Bed & Breakfast on the Honga River UNIT B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
NEWLY RENOVATED ROOMS! A historic Lodge on the Honga River and the Chesapeake Bay, Riverside Lodge offers overnight acco ...
From $270 per night (USD)VRBO
- Click For Pricing
Expedia
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
Welcome to our year-round waterfront retreat on 5 acres with breathtaking views on Hudson Creek. Perfect for family reun ...
Click For PricingExpedia
- From $270 per night (USD)
VRBO
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
NEWLY RENOVATED ROOMS! A historic Lodge on the Honga River and the Chesapeake Bay, Riverside Lodge offers overnight acco ...
From $270 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
NEWLY RENOVATED ROOMS! A historic Lodge on the Honga River and the Chesapeake Bay, Riverside Lodge offers overnight acco ...
From $270 per night (USD)Expedia
- From $626 per night (USD)
VRBO
Waterfront Insta-Worthy Sunsets! 5BR w\/ Bikes , Kayaks and 🐾 Friendly
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Priceless waterfront sunsets from every view in this amazing home. Go back in time and enjoy the Old School Eastern Shor ...
From $626 per night (USD)VRBO
- From $256 per night (USD)
Expedia
Historic Hoopersville Getaway on Chesapeake Bay!
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 18
The historic Queen Anne Victorian vacation rental home is the perfect getaway for friends and family. With 7 bedrooms, 2 ...
From $256 per night (USD)Expedia
- From $762 per night (USD)
VRBO
Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Beautiful Private Retreat with Pool located on Covey Creek The Bird's Nest on Covey Creek is a comfortable and well-appo ...
From $762 per night (USD)VRBO
- From $159 per night (USD)
Expedia
360° Water Views, Hoopers Island Vacation Studio, Fishing Creek
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
WATERFRONT & WATERBACK, 360° views! Hoopers Island Bayside Haven; romantic, scenic, peaceful GETAWAY, SPACIOUS 1 bedroom ...
From $159 per night (USD)Expedia
- From $900 per night (USD)
VRBO
Need a vacation? Walk to the waterfront 🌊 at the Bungalow ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Island Living at our Bayside Bungalow! RELAX while you turn back time and enjoy chasing the sunsets on the beautiful Ch ...
From $900 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Riverside Lodge Bed & Breakfast on the Honga River UNIT A
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
NEWLY RENOVATED ROOMS! A historic Lodge on the Honga River and the Chesapeake Bay, Riverside Lodge offers overnight acc ...
From $270 per night (USD)Expedia
- Click For Pricing
VRBO
Waterside 4-Bedroom Chesapeake Styled Townhome
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Have fun with the whole family. Located on the grounds of a beautiful resort. This Chesapeake styled townhome features 4 ...
Click For PricingVRBO
- From $1230 per night (USD)
Expedia
Short drive to Downtown Cambridge | Sleeps 22 | Pool | Private Dock | Kayaks | P
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 22
Multi-Family Compound with Loads of Amenities - Pool, Beach, Beach Volleyball & More! Hudson Manor is fabulous for large ...
From $1230 per night (USD)Expedia
- From $1777 per night (USD)
VRBO
Short drive to Downtown Cambridge | Private Dock | Sleeps 22 | Pool | Hot Tub |
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 22
When a list of vocabulary words such as 'unique', 'remarkable', and 'spectacular' still fail to describe how special a p ...
From $1777 per night (USD)VRBO
- From $989 per night (USD)
Expedia
Short drive to Downtown Cambridge | Pool | Private Dock | Game Room | Stunning V
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 20
With over 6500 square feet of living space, tall ceilings, and spacious rooms, this modern farmhouse offers plenty of sp ...
From $989 per night (USD)Expedia
- From $950 per night (USD)
VRBO
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 18
Choptank oasis offers the perfect Eastern Shore experience: 200' pier great for crabbing and fishing, river kayaking/ca ...
From $950 per night (USD)VRBO
- From $320 per night (USD)
Expedia
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
WATERFRONT! HOT TUB! KAYAKS! Relax with the entire family at this peaceful 3 bedroom private waterfront cottage on a qui ...
From $320 per night (USD)Expedia
- From $208 per night (USD)
VRBO
Waterfront Cottage in Beautiful Hoopers Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come relax and unwind at this updated two bedroom waterfront property. Bring your boat and tie off on our pier. Enjoy ...
From $208 per night (USD)VRBO
- From $274 per night (USD)
Expedia
Dorchester County Home Near Choptank River!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Head to Cambridge, Maryland, for a relaxing retreat on the Eastern Shore! Located between the Choptank River and the his ...
From $274 per night (USD)Expedia
- From $356 per night (USD)
VRBO
Private, gated country home with outdoor pavilion & EV charger - dog-friendly
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Hinterland House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $356 per night (USD)VRBO
- From $670 per night (USD)
Expedia
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Welcome to The Blue Heron, named for "Henry", the Heron that visits daily. Spacious areas for large groups to gather a ...
From $670 per night (USD)Expedia
- 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 $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 $685 per night (USD)
VRBO
Large Luxury Townhouse with Elevator adjacent to the Chesapeake Hyatt
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a 4 Bedroom, 3.5 Bath LUXURY townhouse overlooking the 1st hole of the RiverMarsh Golf Course at the Hyatt Regency ...
From $685 per night (USD)VRBO
- From $922 per night (USD)
Expedia
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
From the hosts that have maintained a five star ratings on our cottage vacation rental, we would like to invite you to e ...
From $922 per night (USD)Expedia
- From $1199 per night (USD)
VRBO
Chesapeake Waterfront- 7bd\/5ba, Beach, Pool, Pets, Dock
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 18
** Pool open April 1 - Book 3 nights get the 4th FREE through April ** Families and groups LOVE our 7 Bedroom, 5 Bath lu ...
From $1199 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Waterfront Getaway on the Choptank River
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedroom 1 bath home situated on 2 acres. Home comes equipped with sleeper sofa and all the outdoor possibilities the w ...
From $250 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Family and Pet-Friendly, Waterfront with Pier
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
There are two houses on the property. In June of 2015 we completed a full and total re-build of the carriage house and ...
From $275 per night (USD)VRBO
- From $686 per night (USD)
Expedia
Multi-Generational Waterfront Retreat with Pool. 2 weeks still open. 10% off.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
2024 will be our sixth year that we have invited guests to rent summer weeks at our home. We think it is a very special ...
From $686 per night (USD)Expedia
- From $799 per night (USD)
VRBO
Hudson Creek Gorgeous Private Home Awaits your arrival. This place has it all!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 15
Our House is coming on the market soon - We are in the process of purchasing it and anticipating close by the end of Jun ...
From $799 per night (USD)VRBO
- Click For Pricing
VRBO
Victorian Home In Historic West End
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
Victorian home in the Cambridge West End historic district. 3 blocks from water; walk to main street, & on one of the pr ...
Click For PricingVRBO
- From $436 per night (USD)
VRBO
Attractive Waterfront Home over looking Choptank River. Sleeps 5
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This remolded waterfront home has a open floor plan for entertaining and comfortable living. The view of the river is f ...
From $436 per night (USD)VRBO
- From $540 per night (USD)
VRBO
Waterfront Nature\/Outdoor Lovers Secluded Estate
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Thunderstick Lodge is 158-acre outdoor lovers paradise. This late 1800s built estate was totally remodeled in 2020. Eigh ...
From $540 per night (USD)VRBO
- From $591 per night (USD)
VRBO
Waterfront Haven in Cambridge, Md - sleeps 10, 4 bedrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our newly renovated 1920s Waterfront bungalow, where there is something for everyone. Looking for a getaway ...
From $591 per night (USD)VRBO
- From $264 per night (USD)
VRBO
Quarterdeck at Swan Cove Manor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on 22 acres, the Quarterdeck at Swan Cove Manor is one of five homes on the property. Very private with private ...
From $264 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This charming private waterfront cottage on 7 private acres sits on Marylands beautiful Eastern Shore. Cedar Point cotta ...
From $850 per night (USD)VRBO
- From $405 per night (USD)
VRBO
Modernized classic. Historic district near water.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Well maintained and modernized classic home 3 blocks from the Great Marsh Park on the Choptank River A short walk to dow ...
From $405 per night (USD)VRBO
- From $950 per night (USD)
VRBO
A Beautiful Waterfront Retreat for Family Gatherings!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Come take a break with your extended family and friends to a remote area of Dorchester County, Maryland. With 2.5 acres ...
From $950 per night (USD)VRBO
- From $1421 per night (USD)
VRBO
Mariner at Swan Cove Manor
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 18
The Mariner on Swan Cove has a very private location and awaits your next family vacation getaway. It is one of 5 homes ...
From $1421 per night (USD)VRBO
- Click For Pricing
Expedia
Waterfront Vintage Eastern Shore Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Cedar Grove Beach is a lovely vintage Eastern Shore property perfect for a family vacation or a group of friends to get ...
Click For PricingExpedia
- From $800 per night (USD)
VRBO
House close to Great Marsh Park and Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two story Three bedroom house on tree line street half block from Great Marsh Park and Choptank River walking distance t ...
From $800 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Outrigger at Swan Cove Manor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Nestled on 22 acres the Outrigger is one of 5 homes on the property. Very private, ample parking and a fully stocked kit ...
From $600 per night (USD)VRBO
- From $708 per night (USD)
VRBO
Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 17
Brick rancher nestled on a 23-acre nature hideaway. Large deck attached to a huge screened porch overlooking (private) i ...
From $708 per night (USD)VRBO
- From $300 per night (USD)
VRBO
BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
2 night min. Till June 6 th!! SUMMER…PROMO:: FISHING TRIP IN 18 FOOT FIBERGLASS BOAT!!! FOR THOSE WHO BOOK A “WEEK” VA ...
From $300 per night (USD)VRBO
- Click For Pricing
VRBO
Chesapeake Waterfront with Private Beach & Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
You'll love the guest cottage at Cedar Point Farm because of the expansive water views along nearly a mile of shoreline, ...
Click For PricingVRBO
- From $1500 per night (USD)
VRBO
Waterfront Family Retreat with Pool on 7+ acres!
- Bedrooms:
- 6
- Bathrooms:
- 10
- Sleeps:
- 24
Looking for a place to really enjoy nature, boating, fishing, swimming, family games, campfires and more? Bring your boa ...
From $1500 per night (USD)VRBO
- From $524 per night (USD)
VRBO
Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Create unforgettable memories by reserving your riverside retreat today! The primary bedroom features a luxurious king ...
From $524 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Cottage on Cabin Creek
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The cottage is the perfect place for a couple's get away. The views of Cabin Creek are stunning. You will enjoy beautifu ...
From $250 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Year Round Waterfront Estate \/ Family Reunions \/ Retreats - Sleeps 28
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 28
This 6,900 square foot 7 bedroom 6 - 1/2 bathroom waterfront estate home with enormous swimming pool comfortably sleeps ...
From $1500 per night (USD)VRBO
- From $254 per night (USD)
VRBO
The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Better pricing on other sites, Please look there. 'The Cottage' at Heron Cove is a cozy retreat situated on a scenic p ...
From $254 per night (USD)VRBO
- From $435 per night (USD)
VRBO
BayDreams - IronMan\/Eagleman Retreat on the bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Heavenly sunsets will dazzle you at our Chesapeake Bay vacation home. Whether you are fishing, crabbing, paddle boarding ...
From $435 per night (USD)VRBO
- From $1370 per night (USD)
VRBO
CH Waterfront Home w\/ Dock, Pool, Sandy Beach, Kayaks, 5BR\/3.5BA Sleeps up to 16
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
This magnificent historic home was has been recently renovated to include all the modern day comforts and is situated on ...
From $1370 per night (USD)VRBO
- From $5100 per night (USD)
VRBO
Weddings\/Reunions\/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate
- Bedrooms:
- 17
- Bathrooms:
- 20
- Sleeps:
- 60
***Waterfronts homes with pools are booked until September 13, 2020. We are also taking reservations for 2021*** This es ...
From $5100 per night (USD)VRBO
- From $1350 per night (USD)
VRBO
Waterfront 5BR\/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
The Spinnaker at Swan Cove has a great location on 6 private waterfront acres and awaits your next family vacation or ge ...
From $1350 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Peaceful Cambridge Home on Jenkins Creek
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
While we do not include linens/towels, we know you'll find other provided amenities, our convenient location, waterfront ...
From $375 per night (USD)VRBO
- From $728 per night (USD)
VRBO
A Vacation Away From It All-Family And Pet Friendly
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Built in 1990, this exceptional post and beam Lodge offers over 4,700 square feet with 5 bedrooms and 5 baths. Random-wi ...
From $728 per night (USD)VRBO
- From $222 per night (USD)
VRBO
Private waterfront cottage with pool on Church Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Close to Blackwater National Wildlife Refuge and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfro ...
From $222 per night (USD)VRBO
- From $179 per night (USD)
VRBO
Best Kept Secret By the Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Begin your story on Hooper's Island, surrounded by the Chesapeake Bay and Honga River on Maryland's Eastern Shore. T ...
From $179 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Private Waterfront Family Retreat w\/ Pool Pickleball Basketball and Volleyball
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Beautifully appointed 19th century farmhouse situated on 23 acres of pristine beauty with pool and 2,000 feet of unspoil ...
From $550 per night (USD)VRBO
- From $799 per night (USD)
VRBO
GORGEOUS, WATERFRONT HOME WITH POOL IS PERFECT FOR FAMILIES! WINTER DEALS NOW
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Hudson Creek Beautiful Private Estate has it all and is a Perfect Get Away! Think of it as a Country Home on the Water - ...
From $799 per night (USD)VRBO
- From $750 per night (USD)
Expedia
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Come get away to a private oasis on the Warwick River, 10 minutes from the Hyatt and Historic Cambridge. It's as quiet a ...
From $750 per night (USD)Expedia
- From $985 per night (USD)
VRBO
Private 2 Acre Waterfront Family Retreat with Pool & Pier
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 22
Fishing Cove is a fully-furnished eight-bedroom six-bath private waterfront family-friendly house tucked away in a lush ...
From $985 per night (USD)VRBO
- From $845 per night (USD)
VRBO
Renovated Historic Waterfront Home with Pool, Dock, 200 acres
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 18
Spocott is a 350-year-old house, newly renovated to provide a unique blend of history, environment, and modern comfort f ...
From $845 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Spacious, pet-friendly 3-bedroom home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this updated, single-level home with 3 bedrooms, a separate office (with doors), high-speed wifi, a large FENC ...
From $239 per night (USD)VRBO
- From $1800 per night (USD)
Expedia
Remarkable waterfront property on 270 acres
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 15
Located on the Little Choptank River, Cherry Point Farm is a 280-acre historic sporting estate with over 25,000 feet of ...
From $1800 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Stylish Victorian in Historic District
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the heart of the peaceful Historic District of Cambridge, this Victorian stunner c. 1912 is the place to book ...
From $300 per night (USD)VRBO
- Click For Pricing
Expedia
Waterfront retreat with heated pool, historic guest house.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Beautiful, sun-filled, waterfront home where the Choptank meets the Chesapeake Bay. Water views from nearly every window ...
Click For PricingExpedia
- From $497 per night (USD)
VRBO
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Experience a peaceful waterfront retreat on Maryland’s eastern shore at this stunning Cambridge vacation rental! Complet ...
From $497 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
- From $915 per night (USD)
VRBO
Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 17
This 8BR, 5 BA, 2 HBA property is what you are looking for! Your dream vacation awaits down the lane of Bayberry Cove wi ...
From $915 per night (USD)VRBO
- From $219 per night (USD)
Expedia
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 $219 per night (USD)Expedia
- From $624 per night (USD)
VRBO
365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 13
Get away from the city and forget your worries in this spacious and serene lodge that borders Blackwater National Wildli ...
From $624 per night (USD)VRBO
- From $499 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 $499 per night (USD)Expedia
- From $499 per night (USD)
VRBO
Pristine 5 Acre Home\/Pool\/Pool House
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bring the whole family to this great place with lots of room for fun. Located on 5 acres, this home boosts a large pool, ...
From $499 per night (USD)VRBO
- From $295 per night (USD)
Expedia
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)Expedia
- From $243 per night (USD)
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 ...
From $243 per night (USD)VRBO
- From $330 per night (USD)
VRBO
Nanticoke River Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
The whole group will be comfortable in this spacious and unique space. A true historic Vienna home near the Nanticoke Ri ...
From $330 per night (USD)VRBO
- From $339 per night (USD)
VRBO
Luxe Chesapeake Getaway \/ 3-Bedroom Townhome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
✢ Gorgeous new townhome on the historic Cambridge waterfront ✢ Adjacent to the beautiful Downtown with shops, restaurant ...
From $339 per night (USD)VRBO
- From $228 per night (USD)
Expedia
The Schultz Estate
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Historic restored home on 8.5 acres, beautiful setting with wild life including deer, white heron, fox turtle and rabbit ...
From $228 per night (USD)Expedia
- From $414 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 $414 per night (USD)VRBO
- From $325 per night (USD)
Expedia
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 $325 per night (USD)Expedia
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Expedia
Waterfront Hoopers Island Light House Point Vacation Rental Sunsets pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Hoopers Island Light House Point Vacation Rental Open Water Views for miles! Water access from Faux beach Dock area as s ...
Click For PricingExpedia
- From $100 per night (USD)
Expedia
Casa Maria heart of downtown Cambridge Maryland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Short term rental up for your consideration. We are offering this newly renovated first floor apartment that has the fo ...
From $100 per night (USD)Expedia
- From $295 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 $295 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $331 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 $331 per night (USD)VRBO
- From $550 per night (USD)
Expedia
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)Expedia
- 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 $656 per night (USD)
Expedia
Cambridge Beach Home on Choptank River w\/ Pier!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Your next waterfront retreat awaits at this 5-bedroom, 3-bath Cambridge vacation rental! This lovely property features 5 ...
From $656 per night (USD)Expedia