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, (38 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is CA $214
CA $349 total
includes taxes & fees
Aug 30 - Aug 31
Sailwinds Loft at Cambridge Creek
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

2. 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 $277
CA $584 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

3. Pet-Friendly Pond Cottage • Nature Escape Near Beaches

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
The price is CA $179
CA $219 total
includes taxes & fees
Sep 21 - Sep 22
Pet-Friendly Pond Cottage • Nature Escape Near Beaches
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

4. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (65 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is CA $318
CA $383 total
includes taxes & fees
Sep 2 - Sep 3
Waterfront Getaway with Dock
A wooden interior with a dining area, sofas, and a table.

5. 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, (14 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 $488
CA $925 total
includes taxes & fees
Sep 1 - Sep 2
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A marina with boats docked, a water tower, and residential buildings with balconies.

6. Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Pool • 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 CA $450
CA $960 total
includes taxes & fees
Sep 2 - Sep 3
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

7. 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)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $438
CA $827 total
includes taxes & fees
Sep 2 - Sep 3
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

8. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is CA $589
CA $741 total
includes taxes & fees
Sep 7 - Sep 8
Sunset Breezes - quiet waterfront retreat
A house with a large lawn and a dock extending into a calm lake.

9. 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 $374
CA $450 total
includes taxes & fees
Aug 28 - Aug 29
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A spacious living room with a large TV, blue sofa, and a ceiling fan.

10. 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)
"Really comfortable house, plenty of space. Lovely surroundings for a low-key quiet getaway. *Note, the nearby general store has closed permanently as of 30Apr2026"
United States
Rochelle K.
The price is CA $623
CA $1,072 total
includes taxes & fees
Aug 31 - Sep 1
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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 $374
CA $450 total
includes taxes & fees
Aug 28 - Aug 29
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 $93
CA $345 total
includes taxes & fees
Aug 31 - Sep 1
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)
"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 $170
CA $446 total
includes taxes & fees
Aug 30 - Aug 31
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.

14. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (58 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $216
CA $438 total
includes taxes & fees
Sep 8 - Sep 9
Soul Oasis - home on the Chesapeake Bay
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

15. 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, (6 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $184
CA $380 total
includes taxes & fees
Aug 31 - Sep 1
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A compact kitchen with a checkered floor, a dining table with chairs, and a large wall art piece.

16. Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.0 out of 10, Wonderful, (18 reviews)
"Would definitely stay here again. "
United States
Darlene P.
The price is CA $97
CA $255 total
includes taxes & fees
Sep 1 - Sep 2
Retro Hipster: Close to downtown, dining and fun
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

17. 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, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is CA $148
CA $496 total
includes taxes & fees
Aug 30 - Aug 31
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A sandy beach with footprints, a pier in the distance, and a clear sky.

18. 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 $152
CA $343 total
includes taxes & fees
Sep 16 - Sep 17
Tangier Escape, great place get away from it all on Deal Island, MD.
A bedroom with a bed, bedside tables, a lamp, and a painting on the wall.

19. Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.6 out of 10, Exceptional, (24 reviews)
"Great place "
United States
Myranda R.
The price is CA $131
CA $367 total
includes taxes & fees
Sep 23 - Sep 24
Newly updated 3 bedroom cottage with Solo Stove fire pit

20. 6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is CA $183
CA $375 total
includes taxes & fees
Aug 27 - Aug 28
6 Mi to Salisbury: Forest-view Sanctuary!
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"The upgrade has been great. I don't like the fact you have to leave your room to warm your food up. My view could have been better if the tree was removed. Room was great but they hadn't swept under the couch in awhile. Bed was comfy. The amenities and the food selection from the different restaurants was awesome. CBQ my favorite. Everything is within talking distance. Im not a gambler came to relax and that's what I did."
Rory 2-night trip
Posted 8 hours ago
Rod 'N' Reel Resort

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 $345 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.