Holiday Rentals in Dorchester County

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Top Cities in Dorchester County

Holiday RentalsHoliday Rentals

Cambridge

Cambridge

Our top choices for Dorchester County holiday rentals

Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is €448
includes taxes & fees
5 May - 6 May
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Exterior

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is €279
includes taxes & fees
8 May - 9 May
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Smart TV

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
8.8 out of 10, Excellent, (10 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is €528
includes taxes & fees
3 May - 4 May
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (25 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is €216
includes taxes & fees
13 May - 14 May
Sailwinds Loft at Cambridge Creek
Exterior

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is €279
includes taxes & fees
8 May - 9 May
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Marina

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (11 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is €383
includes taxes & fees
5 May - 6 May
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (43 reviews)
"The place was vey clean, whic is of upmost improtance to me. We loved the veiw and the location."
United States
Crystal H.
The price is €464
includes taxes & fees
27 May - 28 May
Sunset Breezes - quiet waterfront retreat
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (12 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is €369
includes taxes & fees
5 May - 6 May
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (57 reviews)
"Great place, will stay again"
United States
Matt S.
The price is €236
includes taxes & fees
20 May - 21 May
Waterfront Getaway with Dock
Marina

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very good, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is €324
includes taxes & fees
1 Jun - 2 Jun
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is €373
includes taxes & fees
5 May - 6 May
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Iron/ironing board, WiFi, bed sheets

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is €209
includes taxes & fees
19 May - 20 May
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Oven, stovetop

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is €372
includes taxes & fees
9 May - 10 May
40' Bristol sailboat with spectacular views
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is €313
includes taxes & fees
2 May - 3 May
Cottage Located on the Patuxent River!
Marina

Summer is almost here on Smith Island! Get ready for a great season on the Bay

Summer is almost here on Smith Island! Get ready for a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host."
United States
Timothy S.
The price is €259
includes taxes & fees
31 May - 1 Jun
Summer is almost here on Smith Island! Get ready for a great season on the Bay
Beach nearby, sun-loungers, beach towels

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (127 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is €253
includes taxes & fees
5 May - 6 May
Soul Oasis - home on the Chesapeake Bay
Apartment D: Riverfront Grand

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (23 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is €213
includes taxes & fees
3 May - 4 May
Salisbury Riverfront Lofts
Dining

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (13 reviews)
"Pet friendly, easy check out, no cleaning involved."
United States
Naomi B.
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (53 reviews)
"Great little place "
United States
Eric R.
The price is €163
includes taxes & fees
4 May - 5 May
Cottage near the Bay
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

Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland

10/10 Excellent
"Great!"
Henderson 1-night trip
Posted 5 hours ago
Hampton Inn & Suites Salisbury/Fruitland

Find out more about Dorchester County

Holiday Homes in Dorchester County

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