Wingate Vacation Rentals

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Vacation Rentals in Wingate

Exterior
Shewell's A-Frame on Mill Creek

Shewell's A-Frame on Mill Creek

Lusby
10.0 out of 10, Exceptional, (5)
"It was really pretty in this area. We had great weather to go fossil hunting and played in the water. Very relaxing!"
United States
Lani
Shewell's A-Frame on Mill Creek
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
9.6 out of 10, Exceptional, (21)
"The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected. "
United States
Elizabeth M.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Beach
Belle of the Chesapeake Bay

Belle of the Chesapeake Bay

Lusby
9.0 out of 10, Wonderful, (18)
"Plus: nice size house; responsive property manager; kitchen reasonably well equipped; nice shared living area; great to have second refrigerator and stove. Minus: no broom (that we could find); leaves thick and slippery on the driveway and steps (with a broom we could have swept them aside, which would have been very helpful); hot water was SCALDING and it was difficult to get any faucet so that it was hot w/o being too hot (honestly, this would be a safety issue if children were staying at...
United States
Kathleen M.
Belle of the Chesapeake Bay
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

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

Cambridge
10.0 out of 10, Exceptional, (79)
"Good stay overall"
United States
Bill C.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Outdoor pool, a heated pool
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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

Woolford
9.8 out of 10, Exceptional, (74)
"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."
United States
Susan G.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Outdoor spa tub
Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons

Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons

Lusby
9.6 out of 10, Exceptional, (4)
"So communicative and thoughtful- helpful throughout and it’s a wonderful house stocked with everything we’d want. Thank you!!"
United States
Elizabeth S.
Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons
Property grounds
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek
10.0 out of 10, Exceptional, (51)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Fridge, microwave, oven, stovetop
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

Point Lookout
10.0 out of 10, Exceptional, (125)
"We had a fantastic stay at the Hideaway in Hays Beach. We were coming up to see our 93yr old Grandmother who lives about 45 minutes away. Our families rented two homes in the area and were able to enjoy our time with three generations that aren’t able to see each other often. The home was exactly as shown, perfectly decorated and incredibly well stocked! We’d absolutely come back!"
United States
Seth H.
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand
Terrace/patio
El Camino

El Camino

Ridge
10.0 out of 10, Exceptional, (49)
"Awesome location and accommodations. Very clean and comfortable. "
United States
Kristen H.
El Camino
Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD

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

Downtown Cambridge
10.0 out of 10, Exceptional, (1)
"Location very convenient, flat beautiful, clean, very friendly, respo sive and accommodating hostess! Thank you!"
United States
Solveig S.
$252 nightly
The price is $267
Dec 9 - Dec 10
Total with taxes and fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

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

Downtown Cambridge
8.8 out of 10, Excellent, (5)
"Should provide assigned parking space. The location is not near the water or close to the water compared to the photo you see when booking. "
United States
Felicia
$280 nightly
The price is $297
Nov 10 - Nov 11
Total with taxes and fees
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Fridge, microwave, oven, stovetop
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

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

Lusby
10.0 out of 10, Exceptional, (53)
"Just what we needed for an extended weekend getaway with family. The view of the water was do nice. House was very clean on arrival "
United States
Kim P.
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

Lusby
10.0 out of 10, Exceptional, (61)
"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
Fridge, microwave, oven, stovetop
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Madison
9.8 out of 10, Exceptional, (7)
"What a wonderful family get away! The house was perfectly appointed with everything we needed. It was spotlessly clean, smelled great and felt comfortable from the get-go. It’s in a quiet location with a really nice view and much larger beach area than we expected. We even got to witness turtles nesting from a distance, saw lots of geese and a bald eagle. Very comfortable beds and wonderful new furnishings. The master bath blew us away! Thank you for such a nice stay! We loved it! "
United States
Sue P.
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
Property grounds
Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

Fishing Creek
10.0 out of 10, Exceptional, (80)
"Great little spot for a long weekend getaway. Very quiet, little traffic. It is remote, so stopping in Cambridge for groceries is recommended."
United States
Robert F K.
Waterfront Cottage in Beautiful Hoopers Island
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock

Waterfront Getaway with Dock

Woolford
10.0 out of 10, Exceptional, (51)
"Great location with everything you may need. It is close to restaurants and Emily’s produce.2nd time staying and will be back again. "
United States
Edna L.
$255 nightly
The price is $270
Nov 10 - Nov 11
Total with taxes and fees
Waterfront Getaway with Dock
On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.

Private Beach Front Getaway at The Sunshine Beach Cottage.

Point Lookout
9.8 out of 10, Exceptional, (80)
"Everything was as advertised. Clean and tidy. Easy to find. Had everything we needed while visiting some state parks. Kids loved the beach and already asked to go back"
United States
Erik S.
Private Beach Front Getaway at The Sunshine Beach Cottage.
Interior
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

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

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.
$623 nightly
The price is $660
Nov 10 - Nov 11
Total with taxes and fees
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Property grounds
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Point Lookout
10.0 out of 10, Exceptional, (124)
"This was the perfect spot for our first vacation with our baby. Quiet, private, and fun! So glad we stayed. "
United States
Paige T.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Fridge, microwave, oven, stovetop
Single family home with screened porch.

Single family home with screened porch.

Fishing Creek
10.0 out of 10, Exceptional, (16)
"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. "
United States
melissa w.
Single family home with screened porch.
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

Comfort Inn & Suites

10/10 Excellent
"The room was extremely clean and the staff were WONDERFUL!! shoutout to Mike at the frost desk for working every day that we stayed and was always there to greet us every morning at breakfast and when we returned. He was so helpful and the breakfast staff kept everything so stocked and fresh. Beautiful room and beautiful location. I had a last minute change of travel plans and they were able to accommodate me! 10/10"
Scarlett 3-night trip
Posted 2 days ago
Comfort Inn & Suites

Find out more about Wingate

Everything you need to know about Wingate vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wingate vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wingate vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wingate vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wingate. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wingate in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $267 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wingate rentals

At Expedia, we put the best Wingate vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wingate rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wingate vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wingate. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks: Visitors like this Wingate vacation home rental. It is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.