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

A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

1. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is HK$1,216
HK$1,913 total
includes taxes & fees
30 Sept - 1 Oct
Sailwinds Loft at Cambridge Creek
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

2. 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, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is HK$1,216
HK$2,861 total
includes taxes & fees
30 Sept - 1 Oct
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

3. 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, (25 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$1,294
HK$2,802 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A bedroom with a bed, a dresser, a mirror, and a window with curtains.

4. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is HK$2,330
HK$3,057 total
includes taxes & fees
12 Oct - 13 Oct
More, than just a place to sleep - welcome home!
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

5. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (67 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is HK$1,804
HK$2,079 total
includes taxes & fees
18 Oct - 19 Oct
Waterfront Getaway with Dock
A wooden interior with a dining area, sofas, and a table.

6. 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, (15 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveller
The price is HK$2,524
HK$4,946 total
includes taxes & fees
30 Sept - 1 Oct
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A lakeside property with a large house, a shed, and a dense forest in the background.

7. 'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
'the Bayside Escape' Remote Chesapeake Bay Estate
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

8. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is HK$2,283
HK$4,441 total
includes taxes & fees
7 Oct - 8 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A spacious living room with a large TV, blue sofa, and a ceiling fan.

9. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (35 reviews)
"Beautiful piece of property and clean, comfortable accommodations! Would definitely return if plan to be in that area again!!"
United States
Joyce F.
The price is HK$2,789
HK$4,926 total
includes taxes & fees
6 Oct - 7 Oct
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A house with a large lawn and a dock extending into a calm lake.

10. 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$2,157
HK$2,453 total
includes taxes & fees
26 Oct - 27 Oct
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A lakeside property with a large house, a shed, and a dense forest in the background.

11. 'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay. They house was beautiful, the amenities were excellent, and we loved the crabs!! We went for a family weekend (mix of 18 kids and adults) and it was very spacious and comfortable for everyone. The pergola in the back was an especially big hit! We highly recommend and would stay again."
United States
Bridget C.
'The Bayside Escape' Remote Chesapeake Bay Estate
A house with a large lawn and a dock extending into a calm lake.

12. 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$1,941
HK$2,224 total
includes taxes & fees
26 Oct - 27 Oct
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A room with a large bed, multiple windows, and a ceiling fan.

13. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is HK$526
HK$1,959 total
includes taxes & fees
1 Oct - 2 Oct
Salisbury Riverfront Lofts
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

14. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is HK$835
HK$2,440 total
includes taxes & fees
5 Oct - 6 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

15. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (63 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is HK$1,059
HK$2,204 total
includes taxes & fees
27 Oct - 28 Oct
Soul Oasis - home on the Chesapeake Bay
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

16. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is HK$974
HK$1,989 total
includes taxes & fees
5 Oct - 6 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A pathway lined with trees and lights leading to a wooden building with a visible window.

17. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is HK$3,624
HK$6,303 total
includes taxes & fees
26 Oct - 27 Oct
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

18. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is HK$2,824
HK$4,782 total
includes taxes & fees
30 Sept - 1 Oct
Turnbridge Manor
A spacious living room with a large sofa, a television, and a view of the ocean.

19. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is HK$2,353
HK$5,314 total
includes taxes & fees
26 Oct - 27 Oct
4-BR Waterfront Turret Home
A sandy beach with footprints, a pier in the distance, and a clear sky.

20. 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, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is HK$863
HK$1,929 total
includes taxes & fees
6 Oct - 7 Oct
Tangier Escape, great place get away from it all on Deal Island, MD.
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

Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

8/10 Good
"Our toilet rocked back and forth and the handle in the shower came off in my hand. Tub had a big patch that had been covered with a hard, sharp glue"
Dawn 3-night trip
Posted 23 hours ago
Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches