Dorchester County holiday rentals

We found 445 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of 118 homes, 11 apartments and other holiday rentals in Dorchester County that are 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

Holiday rentals with weekly discounts - Dorchester County

Showing deals for:21 Nov - 28 Nov

Exceptional

(7 reviews)

New Island Home on the Chesapeake Bay Sunsets

Church Creek, MD

8% off

AU$1,223 per night

includes taxes & fees

Very good

(6 reviews)

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Cambridge, MD

12% off

AU$326 per night

includes taxes & fees

Exceptional

(15 reviews)

CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16

Cambridge, MD

8% off

AU$1,906 per night

includes taxes & fees

Backyard view from the deck. Fire pit on the right side of the photo

Exceptional

(131 reviews)

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

Cambridge, MD

8% off

AU$722 per night

includes taxes & fees

Exceptional

(21 reviews)

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Easton, MD

8% off

AU$606 per night

includes taxes & fees

Exceptional

(12 reviews)

Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier

Cambridge, MD

8% off

AU$2,403 per night

includes taxes & fees

Exceptional

(6 reviews)

Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.

Cambridge, MD

8% off

AU$668 per night

includes taxes & fees

Exceptional

(51 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,15%off 7day stay

Cambridge, MD

8% off

AU$1,465 per night

includes taxes & fees

Exceptional

(6 reviews)

Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD

Cambridge, MD

8% off

AU$889 per night

includes taxes & fees

Exceptional

(7 reviews)

Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres

Vienna, MD

8% off

AU$665 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Dorchester County

Renovated Historic Waterfront Home with Pool, Dock, 200 acres

Sleeps 18 · 7 bedrooms · 4 bathrooms

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

Sleeps 10 · 5 bedrooms · 2+ bathrooms

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.