![](https://a0.muscache.com/im/pictures/1ff6d909-5ba6-42f3-9d2c-fa2327780936.jpg)
Vacation rentals with a pool in Dorchester County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Dorchester County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Dorchester County rentals with a pool
House rentals with a pool
![](https://a0.muscache.com/im/pictures/d342f6b7-320b-49ab-af70-b2991d1301ed.jpg?im_w=720)
Superhost
Home in Saint Marys City
4.92 out of 5 average rating, 52 reviewsHistoric Rosecroft
![](https://a0.muscache.com/im/pictures/miso/Hosting-712981554178511773/original/e8fb0e08-538b-4644-ab16-415d19abd740.jpeg?im_w=720)
Superhost
Home in Cambridge
4.8 out of 5 average rating, 15 reviewsChesapeake Sunset Retreat
![](https://a0.muscache.com/im/pictures/06e88964-101e-48c5-b2c4-4d8999edef1f.jpg?im_w=720)
Superhost
Home in Taylors Island
4.7 out of 5 average rating, 82 reviewsThe Marina Oasis in Taylors Island
![](https://a0.muscache.com/im/pictures/miso/Hosting-20123351/original/396a2626-f600-41ff-9de8-0b7647cbcdb7.jpeg?im_w=720)
Guest favorite
Home in Woolford
5 out of 5 average rating, 106 reviewsStarboard on McKeil Point, w/heated pool & hot tub
![](https://a0.muscache.com/im/pictures/hosting/Hosting-781115050008608314/original/4feff941-b7ad-4468-b9b6-04e7b0322531.jpeg?im_w=720)
Home in Cambridge
5 out of 5 average rating, 4 reviewsAlmost Heaven
![](https://a0.muscache.com/im/pictures/miso/Hosting-23324551/original/c9f12f86-9781-406d-bec9-0ad46f305d58.jpeg?im_w=720)
Guest favorite
Home in Ridge
4.86 out of 5 average rating, 44 reviewsWaterfront Paradise with a Private Pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-1047323460862850824/original/a65f5b00-993c-45a1-ac33-10260b9b3b2e.jpeg?im_w=720)
Home in Lusby
5 out of 5 average rating, 4 reviewsOsprey Eyrie on the Chesapeake Bay
![](https://a0.muscache.com/im/pictures/miso/Hosting-662261371457005532/original/15d00a5c-5228-4e30-bf00-a197027085f1.jpeg?im_w=720)
Guest favorite
Home in Tilghman Island
5 out of 5 average rating, 23 reviewsGreat new rates July & August Book now!
Destinations to explore
- Rentals with pools United States
- Rentals with pools Washington
- Rentals with pools Baltimore
- Rentals with pools Maryland
- Rentals with pools Maryland
- Rentals with breakfast Dorchester County
- Rentals with outdoor seating Dorchester County
- Kid-friendly rentals Dorchester County
- Monthly Rentals Dorchester County
- Rentals with a fire pit Dorchester County
- Rentals with a washer and dryer Dorchester County
- Apartment rentals Dorchester County
- Rentals with a kayak Dorchester County
- Beachfront rentals Dorchester County
- Pet-friendly rentals Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Rentals with a patio Dorchester County
- Rentals with a hot tub Dorchester County
- House rentals Dorchester County
- Rentals with lake access Dorchester County
- Rentals with a fireplace Dorchester County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes