Wingate Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Wingate

Sun loungers, beach towels
Soul Oasis - home on the Chesapeake Bay

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
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

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
Property grounds
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Cottage in Fishing Creek

10.0 out of 10, Exceptional, (51)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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
Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD

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
Fridge, microwave, oven, stovetop
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

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
Terrace/patio
El Camino

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
On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.

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.
Fridge, microwave, oven, stovetop
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

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!
Property grounds
Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views

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
Property grounds
Waterfront Cottage in Beautiful Hoopers Island

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
Terrace/patio
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.

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

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
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

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
Beach
Belle of the Chesapeake Bay

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
Property grounds
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 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
Outdoor pool, a heated pool
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

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
Exterior
Lovely Waterfront Houes

Vacation Home in Lusby

Lovely Waterfront Houes
Interior
Waterfront Wildlife Retreat on the Patuxent River

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.
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Top Wingate Hotel Reviews

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

10/10 Excellent
"The room was very clean and the staff was very courteous and professional. "
Deidra 2-night trip
Posted 3 days ago
Comfort Inn & Suites Cambridge

Find out more about Wingate

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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.