Holiday rentals in Deal Island Historic District

4.96 out of 5 average rating, 26 reviews

Home in Solomons

Solomons Yellow House - Waterfront

SheilaRating, 5 stars3 months ago

Really enjoyed holiday get away . Place was located near water with great views. We enjoyed walking around the neighborhood was quaint. The town was was pretty with water on each side with the Christmas lights at night . We truly enjoyed our relaxing stay . Would definitely book again

4.9 out of 5 average rating, 111 reviews

Home in Chincoteague

Chincoteague Island Creekside Cottage

DoloresRating, 5 stars6 months ago

We thoroughly enjoyed our weekend stay. We liked that the home was in a quieter area in Chincoteague but within close proximity to restaurants, activities and especially to Assateague. There were only two of us, but the house could have easily accomodated a family. It was well laid out, clean and amply stocked with all the essentials. It was also tastefully furnished and had comfy couches. My only wish was that the house had cable or one of the movie channels, so that in the evening, we might have relaxed with a show before bedtime. One day, we took Captain Dan's boat tour, a recommendation from Kathleen, and it was an exciting and interesting outing. We traveled the back channels in the marshes where we saw lots of ponies and a bald eagle soared overhead in one area. Captain Dan had lots of stories to share which kept us entertained the whole trip. Since it was our anniversary, we splurged on a five course dinner at the Channel Bass Inn and Restaurant. Food was excellent.

4.98 out of 5 average rating, 125 reviews

Home in Cambridge

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

ChrisRating, 5 stars4 days ago

This was the perfect getaway for three couples (two with kids below the age of two). Large and peaceful enough to enjoy just staying at the house, but also a great home base for exploring everything Cambridge and the Eastern Shore has to offer! We’d all like to come back again!

4.83 out of 5 average rating, 125 reviews

Tiny home in Salisbury

Cattail's Branch

LaurelRating, 5 stars1 day ago

This place is everything you need and nothing you don't. It's minimal and simple - a true tiny home! But we enjoyed every minute of it. The setting against a wildlife area was amazing, we had great privacy from the other homes in the area, the deck was spacious and the fire pit was perfect. Inside everything was clean and comfortable. The back roads to Assateague were gorgeous! The best part was that we had our dog along for the ride too and it was still an affordable stay. Great value!

5 out of 5 average rating, 18 reviews

Apartment in Tangier

The Tarryn Elizabeth Unit A

ChrisRating, 5 stars1 month ago

Very good spot for a small family trip to Tangier (I came alone, so it was more than enough.) The house is spotless, and Travis has some extras there for his guests (coffee, water, fishing rods, board games for young kids on a rainy day.) Travis also sent me the phone number for an evening ferry off the island, which was extremely helpful. I had a great stay at Travis' place, and would stay here again. I hope to soon.

Holiday rentals for every style

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Popular amenities for Deal Island Historic District holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Deal Island Historic District's top sights

Arby's Dockside Bar and Grill4 locals recommend

Arby's General Store4 locals recommend

Deal Island Boat Ramp3 locals recommend

Other great holiday rentals in Deal Island Historic District

4.97 out of 5 average rating, 128 reviews

Home in Fruitland

Amazingly 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.

5 out of 5 average rating, 31 reviews

Home in Chincoteague

The 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.

4.9 out of 5 average rating, 93 reviews

Home in Chincoteague

On 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.

5 out of 5 average rating, 34 reviews

Home in Cambridge

Serene 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!

4.89 out of 5 average rating, 36 reviews

Home in Lusby

Waterfront 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!

4.97 out of 5 average rating, 39 reviews

Home in Taylors Island

A 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!

5 out of 5 average rating, 28 reviews

Home in Scotland

Bay 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!