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 living room with two grey sofas, a coffee table, and a ceiling fan.

1. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is CA $135
CA $460 total
includes taxes & fees
Oct 17 - Oct 18
Cambridge Apt in Walkable Neighborhood
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

2. 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 $221
CA $361 total
includes taxes & fees
Oct 18 - Oct 19
Sailwinds Loft at Cambridge Creek
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

3. 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 $242
CA $547 total
includes taxes & fees
Nov 3 - Nov 4
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A bedroom with a bed, dresser, and a door.

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

More, than just a place to sleep - welcome home!
Cambridge
The price is CA $425
CA $572 total
includes taxes & fees
Oct 13 - Oct 14
More, than just a place to sleep - welcome home!
A living room with two grey sofas, a coffee table, and a ceiling fan.

5. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
Cambridge
8.0 out of 10, Very good, (4 reviews)
"great location."
United States
Anonymous traveller
The price is CA $94
CA $472 total
includes taxes & fees
Oct 17 - Oct 18
Cambridge Apt in Walkable Neighborhood
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

6. 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 $295
CA $357 total
includes taxes & fees
Oct 18 - Oct 19
Waterfront Getaway with Dock
A wooden interior with a dining area, sofas, and a table.

7. 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 $443
CA $881 total
includes taxes & fees
Oct 13 - Oct 14
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A spacious living room with a large TV, blue sofa, and a ceiling fan.

8. 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 $449
CA $890 total
includes taxes & fees
Oct 13 - Oct 14
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

9. 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 $392
CA $782 total
includes taxes & fees
Oct 14 - Oct 15
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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 $392
CA $473 total
includes taxes & fees
Oct 13 - Oct 14
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A house with a large lawn and a dock extending into a calm lake.

11. 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 $353
CA $425 total
includes taxes & fees
Oct 13 - Oct 14
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A room with a large bed, multiple windows, and a ceiling fan.

12. 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 $88
CA $348 total
includes taxes & fees
Nov 12 - Nov 13
Salisbury Riverfront Lofts
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

13. 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)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is CA $160
CA $454 total
includes taxes & fees
Oct 20 - Oct 21
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

14. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $140
CA $485 total
includes taxes & fees
Oct 19 - Oct 20
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Three birds perched on a wooden structure by the water.

15. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is CA $1,139
CA $1,976 total
includes taxes & fees
Oct 13 - Oct 14
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
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 $169
CA $368 total
includes taxes & fees
Oct 13 - Oct 14
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

17. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $218
CA $382 total
includes taxes & fees
Oct 13 - Oct 14
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

18. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is CA $170
CA $413 total
includes taxes & fees
Oct 13 - Oct 14
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A lakeside view with chairs and a table, a rainbow, and trees.

19. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is CA $295
CA $505 total
includes taxes & fees
Oct 13 - Oct 14
Bright and airy waterfront getaway
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.

20. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is CA $513
CA $881 total
includes taxes & fees
Oct 13 - Oct 14
Turnbridge Manor
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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"The resort was beautiful and very well maintained, the staff were accommodating and went out of their way to make sure we had what we needed or asked for. My only negative would be to make access to links/online information for room service, and restaurant menus. I spent too much time trying to navigate to find these things based on the flyers I was given at check in. For visitors who are not computer savvy, this is very challenging. But other than that, would love to come and stay again."
Debra 1-night trip
Posted 7 hours ago
Hyatt Regency Chesapeake Bay

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 $454 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.