Dorchester County Vacation Rentals

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Dorchester County Vacation Rentals

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

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

Cambridge MD
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Hot Tub
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

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

Cambridge MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

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

Cambridge MD
Guests staying at this vacation home enjoy an outdoor pool, an arcade/game room, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Kitchen
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge MD
At this cottage, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Pool
Kitchen
250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!

250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!

Church Creek MD
At this vacation home, guests have access to features like laundry facilities.
Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

Fishing Creek MD
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Pet friendly
Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"

Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"

3 out of 5
East New Market MD
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this beach vacation home include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek MD
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
Waterfront property with private boat ramp and new dock!

Waterfront property with private boat ramp and new dock!

Cambridge MD
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Cambridge MD
$558 nightly
The price is $591 total per night
$591 total
Dec 23 - Dec 24
Total with taxes and fees
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills.
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

Port Republic MD
At this cabin, guests have access to a garden.
Pool
Kitchen
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton MD
Guests staying at this vacation home enjoy an outdoor pool, an arcade/game room, and laundry facilities. Other amenities at this beach vacation home include barbecue grills and a garden.
Pool
Kitchen
Salisbury Riverfront Lofts

Salisbury Riverfront Lofts

3 out of 5
501 W Main St Salisbury MD
$250 nightly
The price is $269 total per night
$269 total
Dec 28 - Dec 29
Total with taxes and fees
At Salisbury Riverfront Lofts, guests have access to features like laundry facilities. You can put free parking to good use if you drive.
Kitchen
Parking included
Tiny, Funky, and Full of Love - Welcome to the Love Shack

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

Piney Point MD
Guests staying at this apartment enjoy a hot tub, laundry facilities, and a garden. This smoke-free apartment building also has barbecue grills.
Hot Tub
Washer
Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay

Deale MD
Guests of this vacation home enjoy access to a water park, laundry facilities, and a water dispenser. Other amenities at this family-friendly vacation home include barbecue grills and a garden.
Kitchen
Washer
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

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

Stevensville MD
Guests staying at this cottage enjoy a sauna, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
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
Stevensville MD
At this houseboat, guests have access to barbecue grills.
Kitchen
Pet friendly
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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.

Hotel Options in Dorchester County

    Hyatt Regency Chesapeake Bay

    Hyatt Regency Chesapeake Bay

    100 Heron Blvd Cambridge MD
    $176 nightly
    The price is $200 total per night from Jan 1 to Jan 2
    $200 total
    Jan 1 - Jan 2, 2026
    Total with taxes and fees
    8.6/10 Excellent! (1,001 reviews)
    Comfort Inn & Suites Cambridge

    Comfort Inn & Suites Cambridge

    2936 Ocean Gtwy Cambridge MD
    $105 nightly
    The price is $117 total per night from Dec 28 to Dec 29
    $117 total
    Dec 28 - Dec 29
    Total with taxes and fees
    8.2/10 Very Good! (794 reviews)
    Cambridge Inn

    Cambridge Inn

    2831 Ocean Gateway Cambridge MD
    $76 nightly
    The price is $85 total per night from Dec 29 to Dec 30
    $85 total
    Dec 29 - Dec 30
    Total with taxes and fees
    5.2/10 (551 reviews)

Orbitz makes it easy to find vacation rentals in Dorchester County 

🏠 What is the best price for a Dorchester County vacation rental?


Dorchester County rentals range between $85 and $591 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Dorchester County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Dorchester County getaway. Orbitz filters your search results so you can find the best Dorchester County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Dorchester County vacation rentals with Orbitz?


You may be able to cancel or amend your Dorchester County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Dorchester County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Dorchester County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Dorchester County?


When you book a Dorchester County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Dorchester County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Dorchester County—with plenty of hidden gems. We also have plenty of inventory in Dorchester County main cities and near popular attraction spots.


🏠 Why should I book my Dorchester County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Dorchester County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


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