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

Dorchester County Vacation Rentals

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Our top choices for Dorchester County vacation 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 CA $219
CA $357 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $219
CA $520 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $233
CA $534 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $420
CA $563 total
includes taxes & fees
Oct 2 - Oct 3
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 CA $293
CA $352 total
includes taxes & fees
Oct 4 - Oct 5
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 CA $486
CA $930 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $431
CA $829 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $504
CA $953 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $389
CA $469 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $350
CA $420 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $95
CA $354 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $151
CA $438 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $191
CA $415 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $176
CA $372 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $653
CA $1,220 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $509
CA $874 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $424
CA $1,026 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $156
CA $349 total
includes taxes & fees
Oct 5 - Oct 6
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 19 hours ago
Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

Find out more about Dorchester County

Everything you need to know about Dorchester County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dorchester County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dorchester County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Dorchester County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dorchester County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dorchester County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dorchester County vacation rentals we have selected for you start as low as CA $438 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dorchester County rentals

At Expedia, we put the best Dorchester County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Dorchester County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dorchester County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dorchester County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.