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Holiday Rentals in Dorchester County

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Top Cities in Dorchester County

Cambridge
Holiday RentalsHoliday Rentals

Cambridge

Cambridge

Our top choices for Dorchester County holiday rentals

Fridge, microwave, oven, stovetop
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Holiday Home in Cambridge

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
10.0 out of 10, Exceptional, (80)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Exterior
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Cottage in Fishing Creek

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
10.0 out of 10, Exceptional, (51)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Smart TV
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cottage in Cambridge

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (16)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Holiday Home in Cambridge

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
9.8 out of 10, Exceptional, (7)
"Wow! What an incredible property and house. We were a group of families with small kids, and it was heaven for them playing in the pool, on the dock, on the playground, and in the expansive yard. Lots of beautiful sunsets on the patio for the grown-ups too. We never had to leave. Can't recommend highly enough. "
United States
Lea F.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Exterior
Family and Pet-Friendly, Waterfront with Pier

Cottage in Cambridge

Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (265)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier
Exterior
250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!

Holiday Home in Church Creek

250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!
250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!
Property grounds
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Holiday Home in Cambridge

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
9.8 out of 10, Exceptional, (133)
"This was our second time staying here. Love the location and size of the property. Plenty of space for the kids to play catch, ride bikes, and lots of crabbing and fishing. "
United States
Joe B.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Terrace/patio
Waterfront Cottage in Beautiful Hoopers Island

Cottage in Fishing Creek

Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (82)
"Beautiful location, so peaceful and quiet, we loved our stay! "
United States
Janna C.
Waterfront Cottage in Beautiful Hoopers Island
Fridge, microwave, oven, stovetop
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

Holiday Home in East New Market

"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
3.0 star property
10.0 out of 10, Exceptional, (2)
"Clean, well-appointed kitchen. Loved the crab shack!! Would highly recommend. Used the kayaks and canoe. The pool was perfect! The property is beautiful. Highly reccomend"
United States
kathleen l.
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
Property grounds
Waterfront property with private boat ramp and new dock!

Cottage in Cambridge

Waterfront property with private boat ramp and new dock!
9.2 out of 10, Wonderful, (17)
"Clean and convenient. Another bed in the first room would be a suggestion."
United States
Maureen S.
Waterfront property with private boat ramp and new dock!
Smart TV
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Holiday Home in Cambridge

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
United States
Priscilla A.
The price is €541
includes taxes & fees
15 Dec - 16 Dec
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Interior
Floating 2 bed 2 bath condo stunning views of the bay

Houseboat in Stevensville

Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Exterior
Soul Oasis - home on the Chesapeake Bay

Cottage in Lusby

Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (38)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is €245
includes taxes & fees
15 Dec - 16 Dec
Soul Oasis - home on the Chesapeake Bay
Exterior
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Holiday Home in Drayden

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
9.8 out of 10, Exceptional, (78)
"My family and I had a wonderful time. This is a great place to get away from it all. We loved fishing from the dock and having a fire by the water at night. Thanks again for a great time."
United States
Jeramie E.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Terrace/patio
Tiny, Funky, and Full of Love - Welcome to the Love Shack

Apartment in Piney Point

Tiny, Funky, and Full of Love - Welcome to the Love Shack
10.0 out of 10, Exceptional, (14)
"The place had everything we needed and the yard was great for the dogs. Would definitely stay here again."
United States
Dawn B.
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Apartment D: Riverfront Grand
Salisbury Riverfront Lofts

Apartment in Salisbury

Salisbury Riverfront Lofts
3.0 star property
9.4 out of 10, Exceptional, (23)
"It was a great stay nice comfortable place "
United States
Adam
The price is €215
includes taxes & fees
21 Dec - 22 Dec
Salisbury Riverfront Lofts
Terrace/patio
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Cabin in Port Republic

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (181)
"We thoroughly enjoyed our stay in this kitschy, cool, rustic cabin with a million-dollar view. Communing with the ospreys, hummingbirds and the bald eagle who perched numerous times on a nearby tree was an added bonus. And, the owner may be the most friendly/helpful we’ve ever rented from. We hope to be back some day. Thanks!"
United States
Brennan H.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Dining
Million Dollar View of the Chesapeake Bay

Holiday Home in Deale

Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (130)
"Absolutely beautiful and peaceful location. Everything was appreciated- the games for lazy evenings, the crab pots, the comfortable beds and living spaces. Stunning view!"
United States
Michelle D.
Million Dollar View of the Chesapeake Bay
Exterior
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Cottage in Stevensville

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
10.0 out of 10, Exceptional, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
View from property
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

Cottage in Point Lookout

Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand
10.0 out of 10, Exceptional, (125)
"Beautiful home in a stunning location! The house is comfortable and has all the amenities needed for a relaxing retreat. The backyard and beach are really incredible - Hays Beach is my new favorite stretch along the Chesapeake Bay. We plan to return for another family vacation!"
United States
Courtney F.
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dorchester County Hotel Reviews

Best Western Salisbury Plaza

Best Western Salisbury Plaza

10/10 Excellent
"Very sweet and professional young lady. Definitely will recommend this hotel to my employees when they travel this direction. "
Patrick 1-night trip
Posted 4 days ago
Best Western Salisbury Plaza

Find out more about Dorchester County

Holiday Homes in Dorchester County

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