
Holiday rentals in Deal Island Historic District
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Top-rated holiday rentals in Deal Island Historic District
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Deal Island Historic District
Top guest favourite

Home in Fruitland
4.97 out of 5 average rating, 128 reviewsAmazingly convenient yet secluded.
LawrenceRating, 5 stars4 months ago
We stayed for a week over Thanksgiving 2024. Keith and his wife were there to meet us when we arrived and gave us a tour of the house. Very nice people. It's an older house, but it's in good shape. We felt at home once we unpacked. The beds are VERY comfortable--we slept great. Good internet connection. No troubles with any fixtures or equipment. One bathroom is quite small, but we made it work. Convenient to restaurants and shopping--there's a Texas Roadhouse, a Chinese restaurant and a Walmart across the street, a grocery store one stoplight away. Also convenient for us because family lives in Fruitland within a 5 minute drive. The house is on a main road, but we never had trouble making left turns out of the driveway. Turn right and you're a few minutes from the bypass, turn left and you're a block from the main business route through Fruitland and Salisbury. It was a good place to stay.
Top guest favourite

Home in Chincoteague
5 out of 5 average rating, 31 reviewsThe Shell Hunter
KatieRating, 5 stars3 months ago
This has to be the cleanest Airbnb I’ve ever stayed in. It was incredibly comfortable and in a perfect location. I was nervous about bringing my 6 year old here in the winter but we had plenty to do. Janel answers my questions almost immediately and provided so much in her home! I highly recommend this home to anyone looking to stay in the area.
Superhost

Home in Chincoteague
4.9 out of 5 average rating, 93 reviewsOn a Whim, a family retreat!
JeanneRating, 5 stars3 weeks ago
This was a quiet place to stay in the off season. The house was very clean and well equipped with everything we needed.
Top guest favourite

Home in Cambridge
5 out of 5 average rating, 34 reviewsSerene getaway with great waterfront views!
EugeniaRating, 5 stars6 months ago
We recently had a wonderful stay at Travis's place, and we couldn't have felt more at home. The house is not only beautiful but also comfortable, making it the perfect retreat. It’s one of the best-stocked homes I’ve encountered on Airbnb, which made our stay even more enjoyable. Travis was a wonderful host, always responsive and ready to assist with any questions. I truly hope to return in the future. Thank you, Travis, for hosting us in your lovely home!
Superhost

Home in Lusby
4.89 out of 5 average rating, 36 reviewsWaterfront home with three bedrooms,3 full baths
JoyceRating, 5 stars4 days ago
Perfect weekend away! The home backed up to the Chesapeake Bay. The home was very relaxing. Would definitely stay again!
Top guest favourite

Home in Taylors Island
4.97 out of 5 average rating, 39 reviewsA Vacation for All, Away From It All
ChristyneRating, 5 stars4 months ago
If you are looking for a peaceful escape, you found it. Although this home can be used for large gatherings, it is also the perfect getaway for 2. My husband and I loved watching the water and the natural wildlife. DO NOT MISS THE OPPORTUNITY TO EXPERIENCE THIS HOUSE!
Guest favourite

Home in Scotland
5 out of 5 average rating, 28 reviewsBay Front Beach House
DanielleRating, 5 stars7 months ago
Our family's stay at Dana's Bayfront Beach house was absolutely lovely. The house was spacious and looked exactly like the photos with breathtaking views from every room. We loved sitting on the deck and watching the sunrise over the bay in the mornings and the moon rising over a sky full of stars at night. We also enjoyed watching the wildlife. There were Osprey, Jellyfish, crabs, herons and gulls that we could watch from the pier. The kitchen was large and well appointed with pots and pans, dishes and cutlery and we particularly loved the Ninja toaster oven and Keurig coffee maker. We found the beds comfortable and appreciated the AC and ceiling fans which kept us cool even during a very warm and humid week! Thanks Dana! We hope to come back again soon!
Superhost

Home in Princess Anne
4.82 out of 5 average rating, 22 reviewsYe Ole Pirate House
AlessandroRating, 5 stars2 months ago
beautiful quiet place, great host
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- Assateague Island National Seashore
- Jolly Roger Amusement Park
- Ocean City Boardwalk
- Heritage Shores
- Gerry Boyle Park
- Ragged Point Beach
- Cove Point Beach
- Trimper Rides of Ocean City
- Jolly Roger at the Pier
- Assateague State Park
- Sound Beach
- Parramore Beach
- Guard Shore
- Lane Beach
- Wallops Beach
- Langford Sand
- Vir-Mar Beach
- Brownies Beach
- Plantation Lakes Golf and Country Club
- Chesapeake Beach Water Park
- The Links at Lighthouse Sound
- Breezy Point Beach & Campground
- Cedar Island Beach
- Gargathy Beach