Search Holiday Rentals in Wingate

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    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

Top Holiday Rentals in Wingate

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

10.0 out of 10, Exceptional, (51)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

9.8 out of 10, Exceptional, (73)
"We had a wonderful stay including boating, kayaking, swimming, fishing, campfires and crabs! The house was perfect for our group and the owner was very accommodating."
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (77)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (168)
"Rented the house to celebrate a graduation from St Mary’s College. It was perfect. "
Waterfront Wildlife Retreat on the Patuxent River

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

10.0 out of 10, Exceptional, (192)
"Great for our group of 2 families. Plenty of beds, nice gathering space, access to the creek, played in the grassy field. Would/will likely return! "
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (72)
"If you want to relax by the water and getaway from the hustle and bustle, this is the place. The cottage is updated and cozy with amazing views. Just step off the patio onto the sand. Cottage was stocked with essentials and extra goodies to make it feel like home."
Private Beach Front Getaway at The Sunshine Beach Cottage.

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (118)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Casa Maria heart of downtown Cambridge Maryland

9.8 out of 10, Exceptional, (10)
"Place was quiet and clean. Few minutes drive from the center of town. Definitely a great experience!"
The price is £137
includes taxes & fees
22 Sept - 23 Sept
Casa Maria heart of downtown Cambridge Maryland

El Camino

10.0 out of 10, Exceptional, (43)
"Awesome location and accommodations. Very clean and comfortable. "
El Camino

Walk to Beach: Elegant Escape in Lusby!

10.0 out of 10, Exceptional, (1)
"The property was very comfortable, convenient, well organized and beautifully prepared. "
Walk to Beach: Elegant Escape in Lusby!

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (51)
"It’s a wonderful house with everything you need. The views are amazing - perfection! "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Single family home with screened porch.

10.0 out of 10, Exceptional, (12)
"The house was very nicely done and extremely well stocked and the host was very friendly and super easy to deal with. We especially like the location for sunrise walks with the dogs and easy access to the national parks. "
Single family home with screened porch.

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

8.6 out of 10, Excellent, (8)
"Spacious, orderly interior, lovely setting, great amenities: kayaks, fire pit, creek feeds into Chop tank, close to Saint Michaels and Secretary.Big bedrooms with new comfy beds, plenty of bathrooms and showers.Just a lovely place and excellent communication from host."
The price is £513
includes taxes & fees
26 Aug - 27 Aug
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (31)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
The price is £238
includes taxes & fees
24 Aug - 25 Aug
Soul Oasis - home on the Chesapeake Bay

Amazing views waterfront 3-bedroom home in Madison

9.6 out of 10, Exceptional, (5)
Amazing views waterfront 3-bedroom home in Madison

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

2.0 star property
8.4 out of 10, Very good, (7)
"House was spacious plenty of room, great amenities, and very clean! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths

10.0 out of 10, Exceptional, (77)
"Gorgeous property to stay in and celebrate our daughter's graduation from St Mary's College of Maryland. A paradise so close to campus. "
Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9.6 out of 10, Exceptional, (18)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Cottage on the Bay

9.8 out of 10, Exceptional, (8)
"good place to fish good place to enjoy with family quiet and very clean place"
Cottage on the Bay

Belle of the Chesapeake Bay

9.0 out of 10, Wonderful, (14)
"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
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

Frequently asked questions

Can I find a holiday rental in Wingate?

Yes, there are holiday rentals close to the most popular sights in Wingate, or you can select a more secluded option if you're looking for a relaxing stay. Wingate is known for its restaurants.

What are some of the best holiday rentals that Wingate has to offer?

Bay view from Calvert Cliffs, Solomons Island & State Park nearby: This holiday home rental outside of Wingate is located on a lake, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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. Elliott Island and Blackwater National Wildlife Refuge are a couple of places you'll find in the wider area.

What are holiday rentals like in Wingate?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wingate. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.