
Vacation rentals in Dorchester County
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Top-rated vacation rentals in Dorchester County
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Other great vacation rentals in Dorchester County
Top guest favorite

Home in Deal Island Historic District
4.97 out of 5 average rating, 29 reviewsRusty Anchor
RachelRating, 5 stars3 days ago
Rustic and charming, the Rusty Anchor was exactly what we hoped for. The screened porch was a favorite hang out spot. The kitchen sink was absolutely adorable. And the host had tons of family friendly amenities available like a baby bath, beach toys, coloring books, and board games. It looks just like the pictures. Her recommendations for the Washington Inn (now Sugar Water), the local beach, and the produce stand were all fantastic. We didn’t want to leave. If you are looking for a low-key, relaxing get-away, this is the perfect place.
Guest favorite

Home in Taylors Island
5 out of 5 average rating, 15 reviewsHolliday House
JamesRating, 5 stars2 weeks ago
nice quiet place to relax and feel right at home

Home in Cambridge
4.87 out of 5 average rating, 127 reviewsDorothy's Chesapeake Delight
Amy HRating, 5 stars1 week ago
This location was absolutely stunning. Being on the water, having a fire in the fire pit, watching the sunset…everything was amazing! The shower in the bathroom is super vintage and cute. I had never seen one like it in person. Since we went in late spring there were a lot of mosquitoes so bring bug spray or wear long clothes. The house was very cozy and clean. Check in was a breeze. There are a lot of restaurants and stores within 30 mins of the house. Overall, it was a very memorable stay and I would absolutely book again!
Top guest favorite

Home in Fishing Creek
5 out of 5 average rating, 47 reviewsFishing Creek waterfront cottage
SophieRating, 5 stars3 weeks ago
Words cannot express how beautiful and picturesque Robin’s home and property is. I got married on Hoopers Island and we stayed at Robin’s home. The house itself is incredible, from the decorations, to the appliances, to the views; everything was phenomenal! I highly encourage anyone looking for a place to stay on Fishing Creek, to stay at Robins. Robin as a host was incredible. Responsive, generous and so kind. Thank you Robin for making my wedding weekend truly special!
Top guest favorite

Cottage in Princess Anne
5 out of 5 average rating, 7 reviewsWaterfront Cottage in Mt. Vernon
ChristinaRating, 5 stars1 week ago
We had an amazing stay at Melanie’s waterfront home! The location was absolutely perfect right on the water with stunning views and peaceful surroundings. We loved having access to the kayaks, grill, and outdoor furniture it made it easy to relax and enjoy the beautiful setting. The house was fully equipped with everything we needed for a comfortable stay, and the neighborhood was quiet with super friendly neighbors. Melanie was a fantastic host thoughtful, responsive, and even left us a list of local restaurant recommendations, which turned out to be excellent! This spot was exactly what we were looking for, and we’re already looking forward to coming back. Highly recommend!
Superhost

Home in Lusby
4.88 out of 5 average rating, 41 reviewsWaterfront home with three bedrooms,3 full baths
BreckRating, 5 stars3 days ago
Dale is an incredibly proactive and helpful host. He checked in with us several times to ensure we had everything we need and went out of his way to meet us on our schedule to check in and show us around. This is a great spot to relax and look at the ocean or an easy commute to Solomon's Island and all its amenities. You also get access to the community's private beach, which is beautiful and a real asset!
Superhost

Home in Madison
5 out of 5 average rating, 10 reviewsMadison Bay Getaway
MarkRating, 5 stars2 days ago
A beautiful home in a great quiet location. This home has everything you need was a great stay. Ramona is a great host.
Top guest favorite

Cottage in Deal Island Historic District
4.94 out of 5 average rating, 16 reviewsCozy "Waterfront Cottage"
JohnRating, 5 stars9 months ago
The cottage is perfect. For a quiet getaway. We caught blue fish right of the pier. And cooked them same day. We had a great time. The weather was beautiful. Sunsets are spectacular. Thanks Debbie, you are a great host.
Destinations to explore
- Apartment rentals Dorchester County
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- Rentals with a kayak Dorchester County
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- Sandy Point State Park
- Maryland Renaissance Festival
- Quiet Waters Park
- Flounder Pavilion Beach Front - Sandy Point State Park
- Heritage Shores
- Ragged Point Beach
- Plantation Lakes Golf and Country Club
- Breezy Point Beach & Campground
- Gerry Boyle Park
- Brownies Beach
- Idlewilde Restoration Project
- Chesapeake Beach Water Park
- Rose Haven Memorial Park
- Six Flags America
- Quiet Waters Dog Beach
- Oxford Beach
- Matapeake Clubhouse and Beach
- Piney Point Beach
- Lane Beach
- Bayfront Beach
- North Beach Boardwalk/Beach
- Guard Shore
- Sandyland Beach
- Bare Neck Shore