A lighthouse on a pier with a red roof and white walls, surrounded by calm water.

Dorchester County Holiday Rentals

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Our top choices for Dorchester County holiday rentals

Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (34 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is HK$1,216
HK$1,995 total
includes taxes & fees
5 Jul - 6 Jul
Sailwinds Loft at Cambridge Creek
Marina

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

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
7.8 out of 10, Good, (7 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is HK$1,608
HK$3,118 total
includes taxes & fees
20 Jul - 21 Jul
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
9.4 out of 10, Exceptional, (23 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is HK$2,078
HK$3,899 total
includes taxes & fees
28 Jul - 29 Jul
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (59 reviews)
"Great place, will stay again"
United States
Matt S.
Waterfront Getaway with Dock
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)
"Great space. Great location for exploring Cambridge on foot. Check-in easy. Everything clean. Everything works."
United States
Peter G.
The price is HK$2,157
HK$3,982 total
includes taxes & fees
28 Jul - 29 Jul
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
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, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is HK$2,039
HK$3,841 total
includes taxes & fees
28 Jul - 29 Jul
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
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 HK$2,118
HK$2,552 total
includes taxes & fees
17 Jul - 18 Jul
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
9.0 out of 10, Wonderful, (13 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 HK$3,005
HK$5,530 total
includes taxes & fees
8 Jul - 9 Jul
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
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 HK$2,118
HK$2,552 total
includes taxes & fees
17 Jul - 18 Jul
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Marina

Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend getaway at the beautiful gated community. Great water views and a walkable community. The townhouse met all our needs. Fully stocked with essential items. The added bonus is a the workout room with top of the line equipment. A nice touch! Two great decks overlooking the marina. The owners are very responsive."
United States
Melissa
The price is HK$2,737
HK$5,930 total
includes taxes & fees
6 Jul - 7 Jul
Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8
Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is HK$3,576
HK$7,165 total
includes taxes & fees
5 Jul - 6 Jul
'the Bayside Escape' Remote Chesapeake Bay Estate
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is HK$3,772
HK$4,728 total
includes taxes & fees
29 Jul - 30 Jul
Sunset Breezes - quiet waterfront retreat
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, (15 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 HK$2,679
HK$4,910 total
includes taxes & fees
7 Jul - 8 Jul
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (56 reviews)
"Cottage was exactly as listed. Great value"
United States
Tom B.
The price is HK$635
HK$1,463 total
includes taxes & fees
8 Jul - 9 Jul
Cottage near the Bay
2 bedrooms, individually decorated, individually furnished

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (26 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is HK$636
HK$2,082 total
includes taxes & fees
7 Jul - 8 Jul
Salisbury Riverfront Lofts
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (54 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is HK$1,184
HK$2,469 total
includes taxes & fees
13 Jul - 14 Jul
Soul Oasis - home on the Chesapeake Bay
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is HK$812
HK$2,306 total
includes taxes & fees
6 Jul - 7 Jul
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Free WiFi, bed sheets

Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.8 out of 10, Exceptional, (21 reviews)
"Great place "
United States
Myranda R.
The price is HK$808
HK$2,028 total
includes taxes & fees
7 Jul - 8 Jul
Newly updated 3 bedroom cottage with Solo Stove fire pit
Beach

Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is HK$863
HK$1,929 total
includes taxes & fees
15 Jul - 16 Jul
Tangier Escape, great place get away from it all on Deal Island, MD.
Fridge, microwave, oven, stovetop

Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (16 reviews)
"Nice large, bright kitchen, each room has a bathroom! Nice river view, many shops within walking distance and good coffee and breakfast right diwnstairs! Loved the funky, whimsical decor too."
United States
Joan
The price is HK$706
HK$1,657 total
includes taxes & fees
6 Jul - 7 Jul
Retro Hipster: Close to downtown, dining and fun
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

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

10/10 Excellent
"Location, clean room and staff are friendly. Breakfast is good for the price that we pay."
Martheeswaran 1-night trip
Posted less than an hour ago
Comfort Inn & Suites Cambridge