Dorchester County Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Top cities in Dorchester County

A lighthouse on a pier with a boat docked below.
Vacation Rentals

Cambridge

Cambridge

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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
Nov 14 - Nov 15
Cambridge Apt in Walkable Neighborhood
A living room with two grey sofas, a coffee table, and a ceiling fan.

2. 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 $449 total
includes taxes & fees
Nov 14 - Nov 15
Cambridge Apt in Walkable Neighborhood
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, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is CA $250
CA $534 total
includes taxes & fees
Dec 13 - Dec 14
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

4. 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, (15 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is CA $250
CA $534 total
includes taxes & fees
Dec 13 - Dec 14
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

5. 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 $344 total
includes taxes & fees
Nov 18 - Nov 19
Sailwinds Loft at Cambridge Creek
A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

6. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
The price is CA $321
CA $370 total
includes taxes & fees
Nov 14 - Nov 15
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
A marina with boats docked, a water tower, and residential buildings with balconies.

7. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
The price is CA $300
CA $807 total
includes taxes & fees
Nov 15 - Nov 16
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

8. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (69 reviews)
"Excellent stay! Just as described! Very quiet, private location."
United States
Mills Family A.
The price is CA $314
CA $362 total
includes taxes & fees
Nov 16 - Nov 17
Waterfront Getaway with Dock
A dining area with a round table, chairs, and a decorative table runner.

9. 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 $555 total
includes taxes & fees
Nov 16 - Nov 17
More, than just a place to sleep - welcome home!
A wooden interior with a dining area, sofas, and a table.

10. 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, (16 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 $323
CA $633 total
includes taxes & fees
Nov 15 - Nov 16
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A rustic cabin with a sign reading 'A-M-A-L-G-A-M-A-T-E-D' and a small outdoor seating area with two chairs.

11. Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!

Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
Seaford
10.0 out of 10, Exceptional, (1 review)
"This was a clean, comfortable place to stay. We only stayed one night, but would've enjoyed staying longer. Sitting outside with coffee in the morning was special. The number of different birds we heard was amazing. We didn't have time to explore the pond, but it added to a nice, quiet stay."
United States
Whitney H.
The price is CA $154
CA $221 total
includes taxes & fees
Nov 22 - Nov 23
Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

12. 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, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $409
CA $716 total
includes taxes & fees
Nov 19 - Nov 20
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.

13. 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 $452 total
includes taxes & fees
Nov 24 - Nov 25
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A house with a large lawn and a dock extending into a calm lake.

14. 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 $408 total
includes taxes & fees
Nov 16 - Nov 17
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A room with a large bed, multiple windows, and a ceiling fan.

15. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (29 reviews)
"Amazing experience"
United States
Chad
The price is CA $101
CA $362 total
includes taxes & fees
Nov 14 - Nov 15
Salisbury Riverfront Lofts
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

16. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $210
CA $422 total
includes taxes & fees
Nov 18 - Nov 19
Soul Oasis - home on the Chesapeake Bay
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
9.0 out of 10, Wonderful, (16 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 $230
CA $379 total
includes taxes & fees
Nov 14 - Nov 15
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A bedroom with a bed, bedside tables, a lamp, and a painting on the wall.

18. 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, (30 reviews)
"I always stay here when I come for work it’s a pretty nice place quiet and clean I highly recommend it to everyone it’s visiting"
United States
Luis A.
The price is CA $121
CA $349 total
includes taxes & fees
Nov 15 - Nov 16
Newly updated 3 bedroom cottage with Solo Stove fire pit
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

19. 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 $207
CA $424 total
includes taxes & fees
Nov 22 - Nov 23
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Living area

20. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is CA $321
CA $574 total
includes taxes & fees
Nov 18 - Nov 19
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
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.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
Cottage image
Cottages
Cottages

Top Dorchester County Hotel Reviews

A two-story house with a porch, a front door, and a small garden area.
The Wildset

The Wildset

The Wildset
Downtown St. Michaels

10/10 Excellent

Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings.
Canada
Mairi
Reviewed August 11, 2026
The Wildset

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 $94 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.