Find Vacation Rentals in Dorchester County

We have 381 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Dorchester County Vacation Rentals

Find the perfect Dorchester County vacation rental

House Cambridge
from $1,042 per night
House ∙ 16 guests ∙ 5 bedrooms

367 m² House

5.0
Outstanding(60 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $837 per night
16 guests ∙ 5 bedrooms

House

4.8
Outstanding(29 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $969 per night
House ∙ 22 guests ∙ 8 bedrooms

321 m² House

4.8
Outstanding(88 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Taylors Island
from $554 per night
House ∙ 14 guests ∙ 5 bedrooms

362 m² House

5.0
Outstanding(30 ratings)
Taylors Island, Dorchester County, Maryland, United States
Vrbo
Details
House Fishing Creek
from $341 per night
14 guests ∙ 6 bedrooms

House

4.6
Excellent(24 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Vrbo
Details
House Madison
from $1,062 per night
House ∙ 24 guests ∙ 10 bedrooms

418 m² House

5.0
Outstanding(69 ratings)
Madison, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $856 per night
House ∙ 18 guests ∙ 7 bedrooms

418 m² House

5.0
Outstanding(64 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $1,053 per night
House ∙ 28 guests ∙ 7 bedrooms

641 m² House

5.0
Outstanding(90 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $891 per night
House ∙ 16 guests ∙ 8 bedrooms

353 m² House

4.8
Outstanding(5 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
Show more

Recommended Rentals With Pools

House  Cambridge
from $1,084 per night
House ∙ 27 guests ∙ 12 bedrooms

960 m² House

4.7
Excellent(41 ratings)
Cambridge, Dorchester County, Maryland, United States
Pool
Vrbo
Details
Cottage  Cambridge
from $363 per night
Cottage ∙ 4 guests ∙ 1 bedroom

86 m² Cottage

4.9
Outstanding(99 ratings)
Cambridge, Dorchester County, Maryland, United States
Pool
Vrbo
Details
Villa  Fishing Creek
from $819 per night
20 guests ∙ 6 bedrooms

Villa

5.0
Outstanding(6 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Pool
Vrbo
Details
Show more

Pet-Friendly Homes and Apartments

House  Madison
from $718 per night
12 guests ∙ 4 bedrooms

House

Madison, Dorchester County, Maryland, United States
Pet-friendly
Vrbo
Details
House  Cambridge
from $578 per night
House ∙ 15 guests ∙ 4 bedrooms

227 m² House

4.9
Outstanding(142 ratings)
Cambridge, Dorchester County, Maryland, United States
Pet-friendly
Vrbo
Details
House  Taylors Island
from $434 per night
House ∙ 9 guests ∙ 7 bedrooms

195 m² House

5.0
Outstanding(21 ratings)
Taylors Island, Dorchester County, Maryland, United States
Pet-friendly
Vrbo
Details
Show more

Vacation rentals with a balcony

House  Cambridge
from $412 per night
House ∙ 8 guests ∙ 4 bedrooms

167 m² House

5.0
Outstanding(29 ratings)
Cambridge, Dorchester County, Maryland, United States
Balcony
HomeToGo
Details
House  Cambridge
from $454 per night
House ∙ 8 guests ∙ 5 bedrooms

167 m² House

5.0
Outstanding(29 ratings)
Cambridge, Dorchester County, Maryland, United States
Balcony
Vrbo
Details
House  Fishing Creek
from $200 per night
House ∙ 4 guests ∙ 2 bedrooms

149 m² House

4.9
Outstanding(69 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Balcony
Vrbo
Details
Show more

Frequently Asked Questions

How much does it cost to book a vacation rental in Dorchester County?

You can book a vacation rental in Dorchester County for as little as $100 per night.

Can I book a vacation rental in Dorchester County?

On tripping.com, you will find 381 available vacation rental offers in Dorchester County.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Dorchester

Find the best Dorchester vacation rentals on Tripping.com. With over 293 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Dorchester range from $25 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 263 homes in Dorchester offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 110 rentals with pool or jacuzzi, or relax with the family in one of the 257 homes with cable TV. For all those pet owners with dogs or cats, Dorchester offers 118 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 7 vacation rental sites in Dorchester where the top providers in that area are HomeAway, TripAdvisor, and Expedia. There are 210 HomeAway rentals, 28 TripAdvisor short term rentals and 22 Expedia vacation rentals.
image-tag