Vacation rentals in Dorchester County
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Top cities to explore in Dorchester County

Cambridge
Top vacation rentals in Dorchester County

Family and Pet-Friendly, Waterfront with Pier

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Waterfront Cottage in Beautiful Hoopers Island

Waterfront property with private boat ramp and new dock!

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Chesapeake Houseboat Getaway on Kent Island, Maryland

Sweet Bamboo Beach Cottage

Floating 2 bed 2 bath condo stunning views of the bay

Relaxing Waterfront Cottage Near St Michaels, Maryland

The Blue Crab Beach House - Free beach passes

Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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 $600 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.
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