Book for Dorchester County holiday rental accommodation: short-term rental properties & homes| Stayz

Select from 127 homes, 23 cottages and other holiday rentals in Dorchester County to find one that's perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a pool. At the end of the day, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Popular Dorchester County destinations on Stayz

Find spaces that suit your style

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

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Choose a holiday rental for your Dorchester County getaway

Learn about the unique charm of Dorchester County with a stay in a holiday home rental. This city has something for everyone. 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 top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Dorchester County a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

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)
Hog Neck Golf Course (17.6 mi / 28.3 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 an adventurous traveller or just want to appreciate the scenery, Dorchester County is a great place to spend some time outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

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)

Transport options to and around Dorchester County

If you'd prefer to travel by train, the main station serving the city is Cambridge Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in Dorchester County?

The most popular types of holiday homes in Dorchester County are houses. Ready for more choices? Stayz has a variety of options to match the diverse needs of our guests, so you'll see holiday 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 holiday home in Dorchester County?

Property type, length of stay and season are some of the things that can affect the price of a holiday home. Simply click on your dates of travel to find your perfect fit. From cosy cabins to sprawling luxury villas, all Stayz holiday homes 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 Stayz. Did someone just say "private pool"? Use our filters to pick the features and amenities you want in your beach house.

What are popular home amenities in Dorchester County?

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

Are there large group holiday homes in Dorchester County?

With 49 holiday homes that can sleep 10 or more people in Dorchester County, you don't have to keep anyone off the invite list. From family holidays to special events like weddings and birthday parties, Stayz will help you find a large group home 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 Centre

Can I find two-bedroom holiday homes in Dorchester County?

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

Are there holiday homes with WiFi in Dorchester County?

You'll find 67 holiday homes 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 Stayz.

How old do you have to be to rent a holiday home in Dorchester County?

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

How long can I rent a holiday home 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 Stayz 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.