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Compare 84 Vacation Homes in Wingate with updated reviews, rates, and availability.

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2.0 star property
10.0 out of 10, Exceptional, (2)
"Our stay was perfect. The home was quite lovely and equipped with all amenities. The location was very nice. The bay was only a 2 minute walk at the end of the street. Highly recommend."
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was very clean and was great for our home base while visiting family in St. Michael’s. The owner was very response and friendly. The house included all basic amenities and then some! The owner really took the time and care preparing this place for guests. Downtown Cambridge is a short drive and a cute little town with shops and restaurants. We didn’t have a ton of time to explore downtown but plan to on our next stay! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Belle of the Chesapeake Bay

9.4 out of 10, Exceptional, (11)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay

Waterfront home with private dock

10.0 out of 10, Exceptional, (7)
"We stayed here over the Labor Day weekend to celebrate a 40th birthday with friends and family. We had an amazing time and the weather was perfect. We enjoyed using the dock for swimming, crabbing and fishing during the day and enjoyed grilling and fires at night. The kids loved the kayaks, air hockey table and bunkbeds. And the views of the water from the house and patio were excellent! We highly recommend staying here and we will definitely return."
Waterfront home with private dock

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy

Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

9.0 out of 10, Wonderful, (14)
"The place was perfect for our group of friends (4 couples) Everyone had a King Bed, and their own bathroom, We rent our home in NJ so really appreciate how well the house was appointed. It had everything we needed. My only suggestion is a repeater so the internet connectivity is less spotty than we experienced. The TV's kept buffering in the bedrooms. "
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Bay Estate by AvantStay | Waterfront, Private Pond

10.0 out of 10, Exceptional, (1)
"Such a beautiful house, very nice for family or friends get together."
Bay Estate by AvantStay | Waterfront, Private Pond

Cottage on the Bay

9.8 out of 10, Exceptional, (6)
"Clean and accommodating host. Has many of the necessities for the home, including washer/dryer , soaps , trash bags , cleaning essentials , plates/bowls/cups, kitchen gadgets , and more. Home feels safe away from predator animals . Couple deers around. Bring insect repellent."
Cottage on the Bay

Pet-Friendly Quantico Home w/ River Views!

9.6 out of 10, Exceptional, (9)
"Well kept property with very comfortable beds! Breathtaking views of the Wicomico River!!"
Pet-Friendly Quantico Home w/ River Views!

Beautiful Peaceful Home

10.0 out of 10, Exceptional, (2)
"I was deciding between booking a hotel or a home and thankful that we decided on this home for our weekend getaway. After visiting the museums in Cambridge, we were welcomed to our home away from home. Very relaxing, comfortable and spacious for our family. Conveniently located to downtown and nice neighborhood. If looking for a home to stay when in the Cambridge area, this is an excellent choice."
Beautiful Peaceful Home

Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

9.4 out of 10, Exceptional, (3)
"We were in town for a reunion and this was a nice alternative to the local hotels. Updates to the house were nicely done and I love that checkout was simplified to two to three tasks, not a whole laundry list. If I had two suggestions, one would be that the plug-ins were too many and too strong - we considered opening a window for some relief but did not since we were out at the reunion most of the day. But only one per floor would likely be enough although the house is so clean (five stars!)...
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

Solomons Island Waterfront house

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is SAR 1,873
SAR 3,151 total
includes taxes & fees
13 Jan - 14 Jan
Solomons Island Waterfront house

The Schultz Estate

8.4 out of 10, Very Good, (15)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (40)
"The house was amazing clean and functional. "
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (183)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

Historic Hoopersville Getaway on Chesapeake Bay!

9.6 out of 10, Exceptional, (10)
"We had a lovely time on this trip. The house is spacious and the yard/location is great. The kitchen needed a few more things that we could have used but overall we would definitely return. There are no stores nearby so buy everything you need before arriving. You will not regret coming to this house. We made a lot of memories and enjoyed every minute. The host was very attentive and helpful."
Historic Hoopersville Getaway on Chesapeake Bay!

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (71)
"We stayed at Saddle House during 2024 Ironman Maryland, with 2 Ironmans competing and lots of support traveling to stay. I was concerned choosing a house about 20 minutes from the start/finish but it was an amazing choice with great bike route access. House is secluded and serene, amazing cleanliness, kitchen with everything you could ever need. Pictures are very accurate to the product you get. Jon was a great help finding things to do, house has incredible resources that support you during...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Wingate

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (18)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is SAR 484
SAR 1,070 total
includes taxes & fees
13 Jan - 14 Jan
Soul Oasis - home on the Chesapeake Bay

Waterfront home with private dock

10.0 out of 10, Exceptional, (7)
"We stayed here over the Labor Day weekend to celebrate a 40th birthday with friends and family. We had an amazing time and the weather was perfect. We enjoyed using the dock for swimming, crabbing and fishing during the day and enjoyed grilling and fires at night. The kids loved the kayaks, air hockey table and bunkbeds. And the views of the water from the house and patio were excellent! We highly recommend staying here and we will definitely return."
Waterfront home with private dock

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is SAR 432
SAR 859 total
includes taxes & fees
13 Jan - 14 Jan
Deal Island Bay Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.