Wingate Vacation Rentals from CA $1,208: Short-Term Rentals for 2026

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

Private 2 Acre Waterfront Family Retreat with Pool & Pier : Visitors like this Wingate vacation home rental. It is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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Our top choices for Wingate vacation rentals

A hallway with a framed artwork of a bird, a wooden entertainment unit with a TV, and a dining area with a bar stool.

1. Tangier Escape, great place get away from it all on Deal Island, MD.

Deal Island Historic District

Jennifer P.

CA $349 total

includes taxes & fees

Nov 3 - Nov 4

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

2. Deal Island Bay Cottage

Deal Island

Margaret H.

CA $364 total

includes taxes & fees

Oct 25 - Oct 26

A house with a large lawn and a dock extending into a calm lake.

3. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Fishing Creek

Robin E.

CA $421 total

includes taxes & fees

Oct 26 - Oct 27

4. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Fishing Creek

Thomas S.

CA $468 total

includes taxes & fees

Oct 26 - Oct 27

A grassy area with a wooden dock extending into a calm body of water, surrounded by trees and greenery.

5. Waterfront Getaway with Dock

Woolford

Meagan G.

CA $352 total

includes taxes & fees

Oct 25 - Oct 26

A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

6. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

CA $356 total

includes taxes & fees

Oct 26 - Oct 27

A living room with a dark gray sofa, a small round table, and a green throw blanket. There is a brick accent wall and a ceiling fan.

7. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

CA $552 total

includes taxes & fees

Nov 1 - Nov 2

A spacious living room with a large TV, blue sofa, and a ceiling fan.

8. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

Joyce F.

CA $1,055 total

includes taxes & fees

Oct 26 - Oct 27

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Top Wingate Hotel Reviews

Comfort Inn & Suites Lexington Park near Pax River

8/10 Good

"Clean, friendly staff and convenient to multiple areas."

Serenity Bay-Spacious House-Prv Pool-6 bdrms-5baths-Hot Tub-AskAbout 2NightStays

8/10 Good

"Our extended family stayed for a week over Labor Day weekend. I loved the main floor but didn't go up or downstairs due to health issues. I had the master bedroom for which the only issue was adjusting the temperature of the water in the shower. The rental agent was helpful in resolving that.My adult children reported to me that a couple bedrooms were stuffy and the ceiling fans were not much help. Apparently, there was only one floor vent in each room and it was under the bed. Also, the TV in one room did not work. I reported this to the rental agent who said she would see that it was either fixed or replaced but that didn't happen before we left.Those issues were far outweighed by the positives for this home. The kitchen is spacious and very well equipped. We have never had a rental with two refrigerators, two microwaves, two dishwashers, and two sinks! We could not get hot water in one of the sinks, and the filtered water didn't seem to work, but these were minor issues and we did not report them. I really loved the pool and its surrounding area, and spent the majority of my time there. Family was often there every day also.The fire pit was large, comfortable, and set up safely. Bonfires were enjoyable, as were various outdoor areas to congregate, enjoy the beautiful views, and share meals.All in all, it was an enjoyable week in a beautiful home. I'd recommend it to large families."

'The Bayside Escape' Remote Chesapeake Bay Estate

10/10 Excellent

"The house was perfect for us. It was super clean, the beds were all comfortable, and there was plenty of comfortable furniture to gather on. We appreciated that toilet paper, soap, dish soap, coffee filters, etc. were provided. The location was idyllic and serene. It was like staying in an Andrew Wyeth painting. It was the perfect place to have the family gather to cheer on our Ironman!"

Belle of the Chesapeake Bay

10/10 Excellent

"This house was perfect for a short summer getaway with our family, including our 2 grandkids! The beds were super comfortable and the layout of the house worked perfectly for two couples and a family of 4. The boardwalk in Solomons was lovely with beautiful sunsets. We loved the outdoor sculpture garden, the Calvert State Park cliffs by the beach and the awesome mariners museum. The food at the Pier was outstanding, as was the ice cream shop next to the bait and tackle place down the street. All in all, this was a great visit! Glad we found this house to accommodate us so well!"

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wingate vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wingate vacation rentals we have selected for you start as low as CA $1,208 per night. Entering your travel dates in the search wizard 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.

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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: Visitors like this Wingate vacation home rental. It is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

What can I see and do in Wingate?

While you're exploring the area, Blackwater National Wildlife Refuge and Crab Island are a couple of picturesque spots to get outside and enjoy nature. Harriet Tubman Underground Railroad National Historical Park and Elms Beach 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.

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Check prices for these dates

Our top choices for Wingate vacation rentals

1. Tangier Escape, great place get away from it all on Deal Island, MD.

2. Deal Island Bay Cottage

3. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

4. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

5. Waterfront Getaway with Dock

6. Sailwinds Loft at Cambridge Creek

7. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

8. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

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

11. 4-BR Waterfront Turret Home

12. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

13. Lakefront Cabin Near Solomons Island w/ Hot Tub

14. Lakefront Cabin Near Solomons Island w/ Hot Tub

Find vacation rentals that suit your style

Top Wingate Hotel Reviews

Comfort Inn & Suites Lexington Park near Pax River

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Soul Oasis - home on the Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Serenity Bay-Spacious House-Prv Pool-6 bdrms-5baths-Hot Tub-AskAbout 2NightStays

'The Bayside Escape' Remote Chesapeake Bay Estate

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Belle of the Chesapeake Bay

Find out more about Wingate

Frequently asked questions

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