Vacation rentals in Dorchester County

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top vacation rentals in Dorchester County

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

9.76 mi from city center
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

3.53 mi from city center
Get rates
An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

10.08 mi from city center
Get rates
An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

7.41 mi from city center
Get rates
This vacation home features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Laundry facilities are provided for your convenience.
Pool
Hot Tub
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

8.05 mi from city center
Get rates
This vacation home features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. There's a sauna on site, and laundry facilities and concierge services are also offered.
Pool
Hot Tub
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

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

9.25 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

19.79 mi from city center
Get rates
This cottage includes a garden and barbecue grills.
Kitchen
Pet friendly
Waterfront Solomons Apartment

Waterfront Solomons Apartment

26.77 mi from city center
$254 nightly
The price is $269 total per night
$269 total
Nov 4 - Nov 5
Total with taxes and fees
This apartment featured laundry facilities and barbecue grills.
Pool
Kitchen
The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

26.94 mi from city center
Get rates
This vacation home includes a garden and barbecue grills.
Kitchen
Air conditioning
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2 out of 5
28.38 mi from city center
Get rates
This houseboat features barbecue grills.
Kitchen
Pet friendly
Tiny, Funky, and Full of Love - Welcome to the Love Shack

Tiny, Funky, and Full of Love - Welcome to the Love Shack

37.37 mi from city center
Get rates
A hot tub is featured at this apartment, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Washer
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

23.85 mi from city center
Get rates
A garden is available at this cabin.
Pool
Kitchen
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

28.35 mi from city center
Get rates
This vacation home features an outdoor pool and a hot tub. There's a sauna on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

16.75 mi from city center
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

26.11 mi from city center
Get rates
A sauna is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

26.77 mi from city center
$277 nightly
The price is $294 total per night
$294 total
Nov 16 - Nov 17
Total with taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

16.76 mi from city center
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

16.81 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Dorchester County
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

The Best Way to Find Vacation Rentals in Dorchester County 

How cheap is a vacation rental in Dorchester County?


You can find Dorchester County vacation rentals from just $269 per night. 


How do you look for the best vacation rental deals in Dorchester County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Dorchester County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Dorchester County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Dorchester County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Dorchester County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Dorchester County?


Whether you’re a winter wanderer or planning a summer sojourn, Dorchester County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Dorchester County?


Take your pick from the excitement of the big Dorchester County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Dorchester County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Dorchester County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.