Vacation rentals in Wingate

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Top-rated vacation rentals in Wingate

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Solomons

4.96 out of 5 average rating, 26 reviews

Solomons Yellow House - Waterfront

SheilaRating, 5 stars3 weeks 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
Guest favorite

Home in Mechanicsville

4.92 out of 5 average rating, 13 reviews

Modern luxury waterfront retreat, 1 hr to DC

BrookeRating, 5 stars4 weeks ago
This place was amazing! Very clean and beautiful and cozy. We felt right to home, would definitely like to stay again in the warmer months.
Guest favorite

Cottage in North Beach

4.98 out of 5 average rating, 141 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

JonathanRating, 5 stars1 month ago
Daniel’s place was amazing. We stayed for Christmas and it did not disappoint. Daniel had thought of everything from appliances in the kitchen, to games both inside and out and the place was spotless. The beds were extremely comfortable and I have no complaints at all. Would recommend and happily stay again. Enjoyed morning walks along the water.
Guest favorite

Cottage in Chesapeake Beach

4.94 out of 5 average rating, 84 reviews

Cozy Getaway - Breezy Point Beach

JenniferRating, 5 stars4 months ago
Wonderful place! So cute and very clean! The porch was my favorite. Host was very responsive. The kitchen had everything we needed. The only thing i would recommend is a mirror in the master bedroom.
Superhost

Cottage in Heathsville

4.83 out of 5 average rating, 75 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

AllyRating, 5 stars5 months ago
This was a wonderful getaway for my family and friends. We had two toddlers that loved the river beach and pool. There were plenty of toys to keep the kids and adults busy!
Guest favorite

Home in Fruitland

4.97 out of 5 average rating, 128 reviews

Amazingly convenient yet secluded.

LawrenceRating, 5 stars1 month 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.
Guest favorite

Home in Cambridge

5 out of 5 average rating, 14 reviews

"Riverside Retreat"

ValerieRating, 5 stars4 months ago
I had such a great stay at this property and Doug was a great host! The location is fantastic—it's in a friendly, welcoming community that's just a short walk to great restaurants and coffee shops, which was super convenient. The space itself was clean, comfortable, and had a cozy, inviting vibe that made me feel right at home. If you're visiting Cambridge, Maryland, I definitely recommend staying here—it’s the perfect spot for a relaxing getaway. Would stay again in a heartbeat!
Guest favorite

Cottage in Easton

5 out of 5 average rating, 101 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

KathleenRating, 5 stars1 month ago
This was a fantastic place for a relaxing break between the holidays! I loved being right on the river, it was so serene and comfortable. The house was wonderful with the windows looking right out onto the river. I'd definitely recommend this place and hope to return. Cheryl was there to greet me when I arrived and sent great information about things to do in the area.
Guest favorite

Home in Cambridge

4.98 out of 5 average rating, 122 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

BeverlyRating, 5 stars2 months ago
Betty’s place was absolutely immaculate and beautiful! It had everything we needed and was wonderful for creating fun family memories. We would definitely stay here again and have saved it for future visits to Cambridge! Thank you again to our host Betty!
Guest favorite

Cottage in Lottsburg

4.98 out of 5 average rating, 80 reviews

Enchanting Edge of the World Cottage

KirstenRating, 5 stars3 weeks ago
We very much enjoyed Tim’s place. It’s gorgeous and peaceful. Unfortunately we had to cut our trip short due to a snow storm but we would love to come back one day!
Guest favorite

Home in Lusby

4.88 out of 5 average rating, 56 reviews

Beachfront Oasis with Amazing Views

DanielleRating, 5 stars2 months ago
We stayed here for Thanksgiving and thoroughly enjoyed our stay. Great communication from owner. House was clean. Proximity to the ocean was fantastic. Great views and we really enjoyed shark tooth hunting. As stated in the listing, trash had to be taken to a nearby facility. Very easy (and free) process. Would definitely stay here again. 5/5
Guest favorite

Cottage in Saint Leonard

4.98 out of 5 average rating, 130 reviews

Block to Beach, Screened deck, Hot Tub, No CF

LaurenRating, 5 stars3 weeks ago
This was the perfect getaway! The house was so clean and felt like home. The hot tub was perfect for the cold nights after fossil hunting. You can see the beach and water from the back screened deck in the winter and the sunsets are beautiful. Lots of beaches near by to find shark teeth as well. Also there are lots of board games to play. Would definitely book again!

Popular amenities for Wingate vacation rentals

Other great vacation rentals in Wingate

Guest favorite

Home in Montross

4.94 out of 5 average rating, 193 reviews

The Glebe

KevinRating, 5 stars1 month ago
Beautiful home, Beautiful area, and very relaxing!
Guest favorite

Home in Cambridge

5 out of 5 average rating, 34 reviews

Serene getaway with great waterfront views!

EugeniaRating, 5 stars4 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

4.88 out of 5 average rating, 34 reviews

Waterfront home with two bedrooms,3 full bathrooms

PaulRating, 5 stars2 months ago
This was an absolutely perfect coastal getaway, with everything you need to enjoy a laid back time away. Dale is extremely friendly and helpful. He made checking in and checking out straightforward, and he was flexible and accommodating even though we arrived late in the evening. The home has everything you need, including snacks and toiletries in case you forget anything. It's also extremely easy to find and gives you all the privacy and comfort you would want to enjoy the beautiful sunrises over the bay. You won't be disappointed.
Guest favorite

Home in Taylors Island

4.97 out of 5 average rating, 39 reviews

A Vacation for All, Away From It All

ChristyneRating, 5 stars1 month 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!
Superhost

Home in Leonardtown

4.85 out of 5 average rating, 13 reviews

Garden Getaway

ErickaRating, 5 stars4 weeks ago
We had our two dogs with us while we stayed for over 2 weeks waiting to move into our new house. Fenced in yard was a life saver and plenty of room for us to celebrate Christmas
Guest favorite

Home in Scotland

5 out of 5 average rating, 28 reviews

Bay Front Beach House

DanielleRating, 5 stars5 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

4.8 out of 5 average rating, 20 reviews

Ye Ole Pirate House

SusyRating, 5 stars3 months ago
What a charming little house and the host was so kind! h Had everything we needed for a short stay where we could cook our own meals. the area is Beautiful and we will be back!
Guest favorite

Home in Cambridge

5 out of 5 average rating, 15 reviews

Eastern Shore Getaway

StephanieRating, 5 stars3 months ago
My family and I had a wonderful stay at Erika’s place! She was incredibly accommodating and flexible with our check-in time, making the whole process smooth. The house itself was beautiful, spacious, and perfect for spreading out. It’s also very kid-friendly—Erika thoughtfully provided plenty of toys and coloring books, which made the stay even more enjoyable for the little ones.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Dorchester County
  5. Wingate