Dorchester County holiday homes

We found 448 holiday rentals — enter your dates for availability
Discover a selection of 132 homes, 15 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 Bookabach

Holiday rentals with weekly discounts – Dorchester County

Showing deals for:15 Jan - 22 Jan

Room
Property grounds
Dining
Exterior
Exceptional
(9 reviews)

Houseboat on Solomons Island

Solomons

8% off
NZ$4,000
for 7 nights, 1 houseboat
NZ$571 per night
includes taxes & fees
Houseboat on Solomons Island
Dine with panoramic waterfront views—perfect for unforgettable group meals
Wake up to serene water views from the primary suite
Enjoy morning coffee or evening drinks on the private waterfront deck
Interior
Exceptional
(22 reviews)

Chesapeake Bay Waterfront Retreat • 7BR • Sleeps 14 • 2 Homes in 1

Scotland

8% off
NZ$9,465
for 7 nights, 1 home
NZ$1,352 per night
includes taxes & fees
Chesapeake Bay Waterfront Retreat • 7BR • Sleeps 14 • 2 Homes in 1
Living area
Outdoor dining
Interior
Living area
Exceptional
(7 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

12% off
NZ$5,738
for 7 nights, 1 home
NZ$820 per night
includes taxes & fees
Driftwood Haven, Chesapeake Bay views throughout
dining room
Exterior
view from balcony overlooking playhouse, pergola and Brooks Creek
Outdoor banquet area
Exceptional
(277 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

8% off
NZ$4,060
for 7 nights, 1 cottage
NZ$580 per night
includes taxes & fees
Family and Pet-Friendly, Waterfront with Pier
Living area
Exterior
Property grounds
Dining
Wonderful
(17 reviews)

Magnificent Water Front Property

Solomons

7% off
NZ$10,223
for 7 nights, 1 home
NZ$1,460 per night
includes taxes & fees
Magnificent Water Front Property
Living area
Dining
Exterior
Games room
Exceptional
(6 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
NZ$7,616
for 7 nights, 1 home
NZ$1,088 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Foyer with stairs to second floor peak into 1st  floor master bedroom
Foyer into Living Room
Kitchen/dining
Living Room into Kitchen/Dining
Exceptional
(93 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
NZ$7,663
for 7 nights, 1 home
NZ$1,095 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
dining area
entryway
steps to the loft
Exterior
Exceptional
(65 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
NZ$2,326
for 7 nights, 1 cottage
NZ$332 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
Exterior
Aerial view
Aerial view
Exterior
Exceptional
(70 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay

Cambridge

8% off
NZ$12,886
for 7 nights, 1 home
NZ$1,841 per night
includes taxes & fees
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Interior
The view off of the point, breathtaking.
Pool
Another view from above.
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
NZ$8,476
for 7 nights, 1 home
NZ$1,211 per night
includes taxes & fees
Grandview- Main House
Interior
Interior
Exterior
Dining
Wonderful
(7 reviews)

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Royal Oak

8% off
NZ$15,901
for 7 nights, 1 cottage
NZ$2,272 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Interior
Living area
Outdoor dining
Dining
Exceptional
(35 reviews)

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

8% off
NZ$6,764
for 7 nights, 1 home
NZ$966 per night
includes taxes & fees
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Property grounds
Private kitchen
Interior
Room
Exceptional
(11 reviews)

Renovated Waterfront Gem w/ Private Boat Slip & Dock

Secretary

8% off
NZ$4,883
for 7 nights, 1 home
NZ$698 per night
includes taxes & fees
Renovated Waterfront Gem w/ Private Boat Slip & Dock
Living area
Room
Interior
Private kitchen
Exceptional
(17 reviews)

Bay Charm. 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil!

Prince Frederick

8% off
NZ$3,689
for 7 nights, 1 home
NZ$527 per night
includes taxes & fees
Bay Charm. 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil!
Exterior detail
Outdoor dining
Living area
Property grounds
Exceptional
(11 reviews)

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

Huntingtown

8% off
NZ$6,437
for 7 nights, 1 cottage
NZ$920 per night
includes taxes & fees
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(175 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard

6% off
NZ$2,609
for 7 nights, 1 cottage
NZ$373 per night
includes taxes & fees
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
Room
Living area
View of parking pad 1 car is  backed in and 1 for studio on the bay pulled in.
Exterior detail
Exceptional
(31 reviews)

Studio on the Bay.

St. Leonard

8% off
NZ$2,155
for 7 nights, 1 apartment
NZ$308 per night
includes taxes & fees
Studio on the Bay.
Living area
Marina
Private kitchen
Marina
Exceptional
(7 reviews)

New, Intown Waterfront Townhome wPool & Location!

Cambridge

7% off
NZ$6,274
for 7 nights, 1 home
NZ$896 per night
includes taxes & fees
New, Intown Waterfront Townhome wPool & Location!
Convenient open-concept design:  kitchen, dining and living areas
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Exceptional
(165 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
NZ$3,728
for 7 nights, 1 home
NZ$533 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Exterior
Marina
Marina
Property grounds
Exceptional
(14 reviews)

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Cambridge

8% off
NZ$2,727
for 7 nights, 1 apartment
NZ$390 per night
includes taxes & fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Dining
Property grounds
Room
Living area
Exceptional
(32 reviews)

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

Easton

8% off
NZ$4,943
for 7 nights, 1 home
NZ$706 per night
includes taxes & fees
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
Marina
The beautiful marina is just 4 blocks away
Private kitchen
Boutiques and vintage shops are right outside your door
Exceptional
(13 reviews)

Station House East: Upscale Loft in the Historic District Cambridge, MD

Cambridge

7% off
NZ$1,483
for 7 nights, 1 apartment
NZ$212 per night
includes taxes & fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Private kitchen
Exterior
Living area
Dining
Exceptional
(28 reviews)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Cambridge

8% off
NZ$8,974
for 7 nights, 1 home
NZ$1,282 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Interior
Be ready to float! Bring your own inner tubes  and tennis shoes!
Exterior detail
Living area
Exceptional
(145 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
NZ$3,675
for 7 nights, 1 cottage
NZ$525 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery

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:

  • Layton's Chance Vineyard and Winery (10.7 mi / 17.2 km)
  • St. Michaels Winery (16.5 mi / 26.5 km)
  • Chesapeake Beach Water Park (26.2 mi / 42.1 km)
  • Running Hare Vineyard (29.8 mi / 48 km)
  • Talbot Massage (14.4 mi / 23.1 km)
  • Phillips Wharf Environmental Center (17 mi / 27.3 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:

  • 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)
  • Cove Point Beach (21.3 mi / 34.3 km)
  • Flag Ponds Nature Park (22.5 mi / 36.3 km)
  • Matoaka Beach (22.9 mi / 36.8 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? Bookabach 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 Bookabach 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 Bookabach. 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, Bookabach 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, Bookabach 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 Bookabach.
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 Bookabach, 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 Bookabach 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.

More holiday ideas