Vacation Rentals in Dorchester County

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Top Vacation Rentals in Dorchester County

Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (262)
"This was an extension of our original 4-day stay. We had so much wonderful and fun time that we stayed an extra day. The owners Rob and Clarissa were the best host!"
United States
Alicia J.
Family and Pet-Friendly, Waterfront with Pier
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
9.8 out of 10, Exceptional, (7)
"Great House "
United States
Conrad L.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
United States
Ronald S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (13)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
9.8 out of 10, Exceptional, (133)
"Great location with lots of privacy. The dock and the kayaks were a great hit with the family. Really no need to go anywhere. The house was really nice and very spacious. Some of the amenities like the grill and kitchen supplies could use some updating. A nice place to unwind with family and friends."
United States
Lisa T.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (80)
"Beautiful location, so peaceful and quiet, we loved our stay! "
United States
Janna C.
Waterfront Cottage in Beautiful Hoopers Island
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (122)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
7.0 out of 10, Good, (6)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (50)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
United States
Lynne J.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (145)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
$254 nightly
The price is $269
Oct 30 - Oct 31
Total with taxes and fees
Waterfront Solomons Apartment
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"First, Brett is an exceptional host. Very helpful and responsive. This is a very special place in a wonderful community with incredible views. Rustic, warm and the perfect place to relax. We didn’t want to leave! Highly recommend."
United States
Dee D.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
2.0 star property
8.4 out of 10, Very Good, (6)
"Really nice area. I will be returning. Very nice. Thank you!"
United States
Bruce G.
$196 nightly
The price is $210
Oct 30 - Oct 31
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Tiny, Funky, and Full of Love - Welcome to the Love Shack
10.0 out of 10, Exceptional, (12)
"Such a great accommodation!!! We were here for a swim meet in town and Katie was the greatest host. We had all the comforts and amenities needed. We will def be staying again. "
United States
Joleen H.
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Belle of the Chesapeake Bay
9.2 out of 10, Wonderful, (17)
"Excellent communication from the owner, Julie and the property manager. Our family (newborn to adults) stayed at this property while in town for a wedding at Rousby Hall. We were a quick and easy 15 minute drive away from the venue. The house was very clean and nicely set up to accommodate our group. We only wish we had more time to spend at the house than we did. The pictures are exactly what you see when you check in - no unhappy surprises. Thank you for hosting us and being so flexible...
United States
eileen b.
Belle of the Chesapeake Bay
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"Wonderful home and host. Very easy to check-in and communication was excellent. "
United States
Ann T.
$290 nightly
The price is $307
Nov 16 - Nov 17
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
9.8 out of 10, Exceptional, (76)
"The property is just as listed! Thoroughly enjoyed the house, the grounds, and the beach! Rick was accommodating and responsive. What a great place!"
United States
David and Ilana X.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
10.0 out of 10, Exceptional, (125)
"Really enjoyed our time here. The outdoor space in the back was great with the swing and the fire pits. Our kids loved walking to the beach everyday and catching crabs. "
United States
David Z.
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Salisbury Riverfront Lofts
3.0 star property
9.2 out of 10, Wonderful, (22)
"Very nice place clean & roomy."
United States
Brian
$242 nightly
The price is $261
Oct 30 - Oct 31
Total with taxes and fees
Salisbury Riverfront Lofts
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
9.8 out of 10, Exceptional, (43)
"House was beautiful! Right on the bay and easily accommodated our group. "
United States
James T.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
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.
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Top Dorchester County Hotel Reviews

Find out more about Dorchester County

Discover your perfect Dorchester County vacation rental with Expedia

How many vacation rentals are available in Dorchester County?


Expedia has plenty of vacation rentals to choose from in and around  Dorchester County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Dorchester County?


The selection of Dorchester County vacation rentals we have selected for you start as low as $210 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Dorchester County?


Vacation rentals in Dorchester County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Dorchester County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Dorchester County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Dorchester County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Dorchester County?


Find vacation rentals in Dorchester County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Dorchester County.  


What amenities are available in a vacation rental in Dorchester County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Dorchester County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Dorchester County?   


Everytime is a great time to head to Dorchester County! Staying in a Dorchester County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Dorchester County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Dorchester County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Dorchester County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Dorchester County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.