Dorchester County Vacation Rentals, Maryland: house rentals & more

Select from 113 homes, 20 cottages, and other vacation rentals in Dorchester County to find one that's perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, like air conditioning and WiFi. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Dorchester County

Showing deals for:Aug 8 - Aug 15

Exceptional

(6 reviews)

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

Huntingtown, MD

10% off

Exceptional

(7 reviews)

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

East New Market, MD

7% off

Every sunrise brings new hope for a brighter future.

Exceptional

(48 reviews)

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

Fishing Creek, MD

10% off

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Dorchester County

Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate

Sleeps 60 · 20 bedrooms · 16+ bathrooms

Top rated rentals - Dorchester County

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Choose a vacation rental for your Dorchester County getaway

Experience the unique character of Dorchester County with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Dorchester County

Are you looking for things to do in the area? Venture out of your cozy vacation rental and check out everything that makes Dorchester County a one-of-a-kind vacation spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

Layton's Chance Vineyard and Winery (10.7 mi / 17.2 km)
St. Michaels Winery (16.5 mi / 26.5 km)
Hog Neck Golf Course (17.6 mi / 28.3 km)
Perigeaux Vineyards and Winery (25.6 mi / 41.2 km)
Chesapeake Beach Water Park (26.2 mi / 42.1 km)
Running Hare Vineyard (29.8 mi / 48 km)

Exploring the natural landscape of Dorchester County

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Dorchester County is a great place to get out in nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

Long Wharf Park (0.3 mi / 0.6 km)
Gerry Boyle Park at Great Marsh (0.9 mi / 1.4 km)
Blackwater National Wildlife Refuge (10.6 mi / 17.1 km)
Elliott Island (18.6 mi / 30 km)
Middle Hooper Island (21 mi / 33.9 km)
Cove Point Beach (21.3 mi / 34.3 km)

Transportation options to and around Dorchester County

If you prefer train travel, the main station is Cambridge Station.

Frequently asked questions

What is the best area to stay in Dorchester County when booking a vacation rental?

East New Market is one of the most popular neighborhoods to get a Vrbo vacation rental in Dorchester County. Consider our collection of relaxing properties and then go out and experience the best of this destination.

What is the most popular type of vacation rental accommodation in Dorchester County?

According to our data, cottages are the most desirable type of vacation rental in Dorchester County. But that goes without saying, everyone’s idea of an epic stay can vary. Vrbo has vacation rentals in a variety of sizes and shapes, so you’re sure to discover the perfect fit for you.

How much does it cost to rent a vacation rental in Dorchester County?

The average price for a vacation rental in Dorchester County is determined by a number of factors, such as property type, length of stay and season. Whether you’re thinking about a sprawling villa with lots of bedrooms or an apartment just enough for two, just enter your dates of travel to discover some great-value stays.

How much does it cost to rent a beach house in Dorchester County?

Prices for beach houses in Dorchester County will vary depending on the type and size of the property and when you plan to travel. Just enter your travel dates into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filters to refine your search results by amenities, ratings, nearby activities and more.

Are there pet-friendly vacation rentals in Dorchester County?

Pack a travel bag and a bone for your puppy dog because Dorchester County has 39 properties that welcome pets with open arms. Let your happy hound enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check the “Pets allowed” filter box.

Are there large group vacation rentals in Dorchester County?

With 60 vacation rentals that can sleep 10 or more guests in Dorchester County, there’s no need to hold back on your invites. From fun family vacations to events like birthday and Christmas parties, Vrbo will help you find a large group rental to suit the occasion.

Are there one-bedroom vacation rentals in Dorchester County?

Yes, you’ll find 18 one-bedroom properties in Dorchester County to pick from. A one-bedroom vacation rental is an excellent option if it’s just you and your other half or if you’re traveling solo. Throw in more space, privacy and convenience compared to a regular hotel, and you’ve got yourself a memorable trip.

Can I find two-bedroom vacation rentals in Dorchester County?

Dorchester County has 10 two-bedroom vacation properties to pick from. Discover a vacation home with all the comfort and privacy you’re looking for at a price that won’t break the bank on Vrbo.

Are there vacation rentals with WiFi in Dorchester County?

Whether you want to keep up with the latest news, check emails or surf social media, there are 76 vacation homes with WiFi in Dorchester County. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.

How can I find vacation rentals with air conditioning in Dorchester County?

You’ll have your pick of 115 vacation homes with air conditioning in Dorchester County offering that cool, cool breeze and extra level of comfort. Enter your travel dates and then take advantage of our filter tool to help you locate stays with air conditioning.

How old do you have to be to rent a vacation rental in Dorchester County?

Age restrictions can vary across properties on Vrbo, so look at the rules of the vacation home in Dorchester County you’re interested in. But typically, it’s 16, 18 or 21.

How long can I rent a vacation rental in Dorchester County for?

How long you can book a vacation rental in Dorchester County varies according to the property. Just enter your selected travel dates to see a list of options offering extended stays. With tons of creature comforts like kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to find the perfect place to call your home away from home in Dorchester County.

Does Vrbo offer discounts for vacation homes in Dorchester County?

Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some fabulous bargains and discounts on Vrbo. From weekend retreats to extended vacations, we’ve got you covered for your next Dorchester County escape.