Find Vacation Rentals in Dorchester County

We have 365 properties to choose from
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Popular Dorchester County Vacation Rentals

Find the perfect Dorchester County vacation rental

House Cambridge
from $712 per night
House ∙ 16 guests ∙ 5 bedrooms
4.8
Outstanding(29 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $732 per night
House ∙ 16 guests ∙ 5 bedrooms
5.0
Outstanding(60 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Fishing Creek
from $213 per night
House ∙ 14 guests ∙ 6 bedrooms
4.7
Excellent(23 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Vrbo
Details
House Cambridge
from $880 per night
House ∙ 18 guests ∙ 7 bedrooms
5.0
Outstanding(64 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $742 per night
House ∙ 14 guests ∙ 7 bedrooms
5.0
Outstanding(31 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Taylors Island
from $570 per night
House ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding(30 ratings)
Taylors Island, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $876 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(75 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $910 per night
House ∙ 22 guests ∙ 8 bedrooms
4.8
Outstanding(88 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
House Cambridge
from $807 per night
House ∙ 16 guests ∙ 8 bedrooms
4.8
Outstanding(5 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
Details
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Recommended Rentals With Pools

House  Cambridge
from $1,007 per night
House ∙ 20 guests ∙ 7 bedrooms
4.8
Outstanding(8 ratings)
Cambridge, Dorchester County, Maryland, United States
Pool
Vrbo
Details
House  Cambridge
from $835 per night
House ∙ 17 guests ∙ 6 bedrooms
4.9
Outstanding(78 ratings)
Cambridge, Dorchester County, Maryland, United States
Pool
Vrbo
Details
House  Secretary
from $471 per night
House ∙ 10 guests ∙ 5 bedrooms
4.9
Outstanding(12 ratings)
Secretary, East New Market, Dorchester County
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Hoopersville
from $411 per night
House ∙ 15 guests ∙ 8 bedrooms
4.8
Outstanding(27 ratings)
Hoopersville, Dorchester County, Maryland, United States
Pet-friendly
Vrbo
Details
House  Fishing Creek
from $375 per night
House ∙ 15 guests ∙ 7 bedrooms
4.8
Outstanding(27 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Pet-friendly
HomeToGo
Details
House  Madison
from $912 per night
House ∙ 18 guests ∙ 7 bedrooms
4.9
Outstanding(86 ratings)
Madison, Dorchester County, Maryland, United States
Pet-friendly
Vrbo
Details
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Best vacation rentals with a balcony

House  Cambridge
from $1,018 per night
House ∙ 27 guests ∙ 7 bedrooms
4.8
Outstanding(4 ratings)
Cambridge, Dorchester County, Maryland, United States
Balcony
HomeToGo
Details
House  Cambridge
from $366 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(29 ratings)
Cambridge, Dorchester County, Maryland, United States
Balcony
HomeToGo
Details
House  Fishing Creek
from $210 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding(69 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Balcony
Vrbo
Details
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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 $99 per night.

Can I book a vacation rental in Dorchester County?

On tripping.com, you will find 365 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.
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