Find Vacation Rentals in Dorchester County

We have 288 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
$278 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (47 ratings)
Cambridge, Dorchester County, Maryland, United States
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Vrbo
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House Taylors Island
$605 per night
House ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding (32 ratings)
Taylors Island, Dorchester County, Maryland, United States
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Vrbo
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House Taylors Island
$426 per night
House ∙ 15 guests ∙ 5 bedrooms
4.9
Outstanding (25 ratings)
Taylors Island, Dorchester County, Maryland, United States
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Vrbo
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House Algonquin
$672 per night
House ∙ 13 guests ∙ 5 bedrooms
4.9
Outstanding (14 ratings)
Algonquin, Cambridge, Dorchester County
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Vrbo
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House Cambridge
$601 per night
House ∙ 13 guests ∙ 5 bedrooms
5.0
Outstanding (8 ratings)
Cambridge, Dorchester County, Maryland, United States
Details
Vrbo
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House East New Market
$579 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (2 ratings)
East New Market, Dorchester County, Maryland, United States
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Vrbo
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House Fishing Creek
$222 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding (4 ratings)
Fishing Creek, Hoopers Island, Dorchester County
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Vrbo
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House Cambridge
$911 per night
House ∙ 22 guests ∙ 8 bedrooms
4.8
Outstanding (91 ratings)
Cambridge, Dorchester County, Maryland, United States
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Vrbo
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Farmhouse Taylors Island
$561 per night
Farmhouse ∙ 14 guests ∙ 4 bedrooms
4.9
Outstanding (92 ratings)
Taylors Island, Dorchester County, Maryland, United States
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Vrbo
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Recommended Rentals With Pools

House  Madison
$1,050 per night
House ∙ 12 guests ∙ 6 bedrooms
5.0
Outstanding (30 ratings)
Madison, Dorchester County, Maryland, United States
Pool
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Vrbo
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Cottage  Cambridge
$361 per night
Cottage ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding (102 ratings)
Cambridge, Dorchester County, Maryland, United States
Pool
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Vrbo
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House  Cambridge
$574 per night
House ∙ 10 guests ∙ 3 bedrooms
4.6
Excellent (10 ratings)
Cambridge, Dorchester County, Maryland, United States
Pool
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Vrbo
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Pet-Friendly Homes and Apartments

House  Fishing Creek
$344 per night
House ∙ 18 guests ∙ 7 bedrooms
4.8
Outstanding (17 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Pet-friendly
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Vrbo
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House  Woolford
$397 per night
House ∙ 18 guests ∙ 6 bedrooms
5.0
Outstanding (7 ratings)
Woolford, Madison, Dorchester County
Pet-friendly
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Vrbo
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House  Fishing Creek
$254 per night
House ∙ 15 guests ∙ 5 bedrooms
4.9
Outstanding (127 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Pet-friendly
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Vrbo
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Best vacation rentals with a balcony

House  Fishing Creek
$168 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (70 ratings)
Fishing Creek, Hoopers Island, Dorchester County
Balcony
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Vrbo
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House  Taylors Island
$842 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
$584 per night
House ∙ 10 guests ∙ 4 bedrooms
Cambridge, Dorchester County, Maryland, United States
Balcony
Details
Vrbo
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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 $108 per night.

Can I book a vacation rental in Dorchester County?

On tripping.com, you will find 288 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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