Vacation rentals in Dorchester County

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Top cities to explore in Dorchester County

Cambridge

Cambridge

Vacation Rentals
Cambridge

Top vacation rentals in Dorchester County

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

10.08 mi from city center
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An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

9.76 mi from city center
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A hot tub is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

10.35 mi from city center
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Private 9 acre Family Retreat on the Chesapeake Bay

Private 9 acre Family Retreat on the Chesapeake Bay

10.84 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River

26.36 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Cottage near the Bay

Cottage near the Bay

42.33 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Dryer
Chesapeake Houseboat Getaway on Kent Island, Maryland

Chesapeake Houseboat Getaway on Kent Island, Maryland

28.27 mi from city center
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This houseboat features barbecue grills.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

16.79 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

26.94 mi from city center
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This vacation home includes a garden and barbecue grills.
Kitchen
Air conditioning
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

39.86 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

28.35 mi from city center
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This vacation home features an outdoor pool and a hot tub. There's a sauna on site, and laundry facilities and barbecue grills are also offered.
'river's Edge Retreat With Kayaks & River Access!

'river's Edge Retreat With Kayaks & River Access!

3 out of 5
48.63 mi from city center
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This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and barbecue grills. A garden is also provided.
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

26.77 mi from city center
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This vacation home includes a garden and laundry facilities.
Kitchen
Washer
The Cottage

The Cottage

30.06 mi from city center
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This vacation home features laundry facilities.
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

2 out of 5
49.22 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

23.19 mi from city center
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This vacation home features a water park and laundry facilities.
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

40 mi from city center
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This cottage features laundry facilities.
The Lazy Crab Beach House - Free beach passes

The Lazy Crab Beach House - Free beach passes

26.58 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
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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.

The Best Way to Find Vacation Rentals in Dorchester County 

How cheap is a vacation rental in Dorchester County?


You can find Dorchester County vacation rentals from just per night. 


How do you look for the best vacation rental deals in Dorchester County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Dorchester County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Dorchester County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Dorchester County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Dorchester County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Dorchester County?


Whether you’re a winter wanderer or planning a summer sojourn, Dorchester County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Dorchester County?


Take your pick from the excitement of the big Dorchester County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Dorchester County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Dorchester County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.