Find Vacation Rentals in Dorchester County

We have 301 properties to choose from
Dorchester County
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Dorchester County
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Popular Dorchester County Vacation Rentals

Find the perfect Dorchester County vacation rental

House Cambridge
from $702 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (28 ratings)
Cambridge, Dorchester County, Maryland, United States
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House Hoopersville
from $434 per night
House ∙ 15 guests ∙ 7 bedrooms
4.8
Outstanding (26 ratings)
Hoopersville, Dorchester County, Maryland, United States
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Vrbo
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House Cambridge
from $905 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding (68 ratings)
Cambridge, Dorchester County, Maryland, United States
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Vrbo
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Cottage Cambridge
from $300 per night
Cottage ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (278 ratings)
Cambridge, Dorchester County, Maryland, United States
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House Cambridge
from $300 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (46 ratings)
Cambridge, Dorchester County, Maryland, United States
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House East New Market
from $609 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (5 ratings)
East New Market, Dorchester County, Maryland, United States
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House Taylors Island
from $628 per night
House ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding (30 ratings)
Taylors Island, Dorchester County, Maryland, United States
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House Cambridge
from $661 per night
House ∙ 16 guests ∙ 5 bedrooms
4.8
Outstanding (26 ratings)
Cambridge, Dorchester County, Maryland, United States
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House Fishing Creek
from $494 per night
House ∙ 15 guests ∙ 5 bedrooms
4.9
Outstanding (133 ratings)
Fishing Creek, Hoopers Island, Dorchester County
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Vacation rentals and apartments with air conditioning

House  Madison
from $538 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (31 ratings)
Madison, Dorchester County, Maryland, United States
Air conditioning
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House  Cambridge
from $462 per night
House ∙ 12 guests ∙ 3 bedrooms
4.6
Excellent (10 ratings)
Cambridge, Dorchester County, Maryland, United States
Air conditioning
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House  Cambridge
from $941 per night
House ∙ 22 guests ∙ 8 bedrooms
4.8
Outstanding (84 ratings)
Cambridge, Dorchester County, Maryland, United States
Air conditioning
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Best vacation rentals with a balcony

House  Fishing Creek
from $200 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (68 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Balcony
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House  Taylors Island
from $863 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (68 ratings)
Taylors Island, Dorchester County, Maryland, United States
Balcony
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Vrbo
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House  Cambridge
from $956 per night
House ∙ 16 guests ∙ 5 bedrooms
4.7
Excellent (23 ratings)
Cambridge, Dorchester County, Maryland, United States
Balcony
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Cabins and Homes With Fireplaces

House  Cambridge
from $554 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (28 ratings)
Cambridge, Dorchester County, Maryland, United States
Fireplace
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HomeToGo
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House  Cambridge
from $1,080 per night
House ∙ 27 guests ∙ 7 bedrooms
4.7
Excellent (11 ratings)
Cambridge, Dorchester County, Maryland, United States
Fireplace
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Vrbo
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House  Cambridge
from $960 per night
House ∙ 16 guests ∙ 4 bedrooms
5.0
Outstanding (60 ratings)
Cambridge, Dorchester County, Maryland, United States
Fireplace
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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 $128 per night.

Can I book a vacation rental in Dorchester County?

On tripping.com, you will find 301 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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