Dorchester County Vacation Rentals, Maryland: house rentals & more

Select from 125 homes, 23 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.

Find the best place to stay - Dorchester County

Comfortable, Spacious, Family-Friendly Second living room

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Sleeps 22 · 8 bedrooms · 6 bathrooms

Ransome's Chesapeake Retreats - 250 acres with one mile long of Bay shoreline

EASTERN SHORE/CAMBRIDGE 250 ACRES on CHESAPEAKE BAY VACATION/REUNION sleeps 40

Sleeps 40 · 12 bedrooms · 8+ bathrooms

Our home blends into towering pines, lawns & hundreds of feet of waterfront

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April

Sleeps 18 · 7 bedrooms · 5 bathrooms

Popular Dorchester County destinations on Vrbo

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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:

St. Michaels Winery (16.5 mi / 26.5 km)
Chesapeake Beach Water Park (26.2 mi / 42.1 km)
Layton's Chance Vineyard and Winery (10.7 mi / 17.2 km)
Perigeaux Vineyards and Winery (25.6 mi / 41.2 km)
The Hen House (28.5 mi / 45.9 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:

Harriet Tubman Underground Railroad National Historical Park (9.1 mi / 14.6 km)
Blackwater National Wildlife Refuge (10.6 mi / 17.1 km)
Calvert Cliffs State Park (23 mi / 37 km)
Breezy Point Beach (23.9 mi / 38.4 km)
Long Wharf Park (0.3 mi / 0.6 km)
Great Marsh Park (0.9 mi / 1.4 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 most popular type of vacation rental accommodation in Dorchester County?

The most popular types of vacation rentals in Dorchester County are houses. Ready for more choices? Vrbo has a variety of options to match the diverse needs of our guests, so you'll see vacation homes in loads of shapes and sizes. The ideal fit is ready and waiting for you — discover yours today.

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

Property type, length of stay and season are some of the things that can affect the price of a vacation home. Simply click on your dates of travel to find your perfect fit. From cozy cabins to sprawling luxury villas, all Vrbo vacation rentals provide unbeatable value.

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

When you travel and the size and style of the property will influence the cost of your beachside stay. Put in your Dorchester County travel dates to see all your options on Vrbo. Did someone just say "private pool"? Use our filters to pick the features and amenities you want in your beach house.

What are popular rental amenities in Dorchester County?

Some of the most popular rental amenities people prefer in Dorchester County include a stovetop, a fridge and a microwave oven. Whether you're going on vacation with family, friends or even pets, Vrbo vacation homes include the best amenities for chilling out with the people closest to you.

Are there large group vacation rentals in Dorchester County?

With 49 vacation rentals that can sleep 10 or more people in Dorchester County, you don't have to keep anyone off the invite list. From family vacations to special events like weddings and birthday parties, Vrbo will help you find a large group rental to suit the occasion.

What are the top attractions for families in Dorchester County?

Keeping the kids amused during your stay in Dorchester County is a snap with these leading family-friendly attractions:

Great Marsh Park
Choptank River Lighthouse
Dorchester County Visitors Center

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

Gather your besties and enjoy total privacy and comfort in one of the nine two-bedroom vacation properties Dorchester County has to offer.

Are there vacation rentals with WiFi in Dorchester County?

You'll find 67 vacation rentals with WiFi in Dorchester County. If you want to disconnect from daily life during your trip, but still need to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.

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

The minimum age is generally 16, 18 or 21. It can differ from one property to another on Vrbo, so look at the rules of your preferred Dorchester County vacation home before booking.

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

It's really down to the Dorchester County property. To view a list of options offering extended stays, simply enter your dates and number of people into the Vrbo search page. You can enjoy having the entire place to yourself, along with the comforts of home like air conditioning, a fully-equipped kitchen and outdoor spaces to run around in. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.