Wingate Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Rentals in Wingate

Cottage in Lusby

9.8 out of 10, Exceptional, (38)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is ¥19,385
¥43,562 total
includes taxes & fees
Dec 9 - Dec 10
Soul Oasis - home on the Chesapeake Bay

Vacation Home in Cambridge

10.0 out of 10, Exceptional, (80)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cottage in Fishing Creek

10.0 out of 10, Exceptional, (51)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Vacation Home in Lusby

10.0 out of 10, Exceptional, (63)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
United States
Whitney H.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Condo in Downtown Cambridge

10.0 out of 10, Exceptional, (6)
The price is ¥23,029
¥55,315 total
includes taxes & fees
Dec 8 - Dec 9
Station House East: Upscale Loft in the Historic District Cambridge, MD

Cottage in Point Lookout

10.0 out of 10, Exceptional, (125)
"Beautiful home in a stunning location! The house is comfortable and has all the amenities needed for a relaxing retreat. The backyard and beach are really incredible - Hays Beach is my new favorite stretch along the Chesapeake Bay. We plan to return for another family vacation!"
United States
Courtney F.
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

Cabin in Ridge

10.0 out of 10, Exceptional, (50)
"Great location, the dock is perfect for sunsets, nice balance of waterfront but also cabin vibes"
United States
Alan B.
El Camino

Cottage in Point Lookout

9.8 out of 10, Exceptional, (80)
"We had a very nice and relaxing time on the beach and even got to watch a launch from wallops. "
United States
Ethan B.
Private Beach Front Getaway at The Sunshine Beach Cottage.

Vacation Home in Madison

9.8 out of 10, Exceptional, (8)
"the place was great. easy access to water and toys."
United States
Allen C.
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Vacation Home in Dameron

10.0 out of 10, Exceptional, (5)
"Such a beautiful house, very nice for family or friends get together."
United States
Yu S.
Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views

Cottage in Fishing Creek

10.0 out of 10, Exceptional, (82)
"Beautiful location, so peaceful and quiet, we loved our stay! "
United States
Janna C.
Waterfront Cottage in Beautiful Hoopers Island

Vacation Home in Cambridge

2.0 star property
9.4 out of 10, Exceptional, (6)
"I looked for a place that was on the water, allowed dogs, and had enough beds for our group. This house met all of our needs, and was very comfortable. The fans on the screened porch were appreciated. "
United States
Stephanie S.
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.

Vacation Home in Cambridge

8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
United States
Priscilla A.
The price is ¥53,582
¥102,331 total
includes taxes & fees
Dec 6 - Dec 7
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Vacation Home in Woolford

9.6 out of 10, Exceptional, (21)
"This property is beautiful and perfect for large groups. There is plenty of room and very inviting. We had a great time!"
United States
Shannon T.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Vacation Home in Lusby

9.0 out of 10, Wonderful, (18)
"Spacious home in a quiet neighborhood. We all had our own room. We enjoyed the sunroom. Near Cove Point Park/Pool. We enjoyed taking our kids to the pool and our dogs to the dog park inside Cove Point Park. Communication with Becky was great. I definitely recommend to stay at the Belle! Thank you! "
United States
Jackie T.
Belle of the Chesapeake Bay

Cottage in Point Lookout

10.0 out of 10, Exceptional, (124)
"Perfect place for a quiet getaway at the beach!"
United States
Cheryl S.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Vacation Home in Woolford

9.8 out of 10, Exceptional, (75)
"We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family."
United States
Linda S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Condo in Downtown Cambridge

8.8 out of 10, Excellent, (5)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is ¥20,160
¥46,027 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Vacation Home in Lusby

Lovely Waterfront Houes

Vacation Home in Lusby

10.0 out of 10, Exceptional, (173)
"This property is tops in all of Maryland. If you want to catch crabs in a perfect property this is the place. "
United States
Chrissy L.
Waterfront Wildlife Retreat on the Patuxent River
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Wingate Hotel Reviews

Find out more about Wingate

Search for holiday rentals in Wingate on Expedia! You can easily find your home rentals, villas, holiday apartments in Wingate using one of the methods below:

  • View our selection of featured holiday rentals in Wingate
  • Use the map to find apartments and other holiday homes in the Wingate neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wingate while they last

Look no further and take a look at our great range of rental properties in Wingate!

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Wingate?

Yes, you can find vacation rentals near the most popular points of interest in Wingate, or you can choose a more secluded option if you want a relaxing place to stay. Wingate is known for its restaurants.

What are some of the best vacation home rentals in Wingate?

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28: Visitors like this Wingate vacation home rental. It is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What can I see and do in Wingate?

While you're exploring the area, Lower Hooper Island and Middle Hooper Island are a couple of picturesque spots to get outside and enjoy nature. Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad National Historical Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Wingate?

Vacation rentals are private properties you can reserve for a couple days or more in Wingate. Vacation rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.