Wingate Vacation Rentals

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Vacation Rentals in Wingate

Waterfront Cottage in Beautiful Hoopers Island
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (46)
"Comfortable, clean home directly on the Chesapeake Bay."
Private Beach Front Getaway at The Sunshine Beach Cottage.
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (6)
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is $130
$285 total
includes taxes & fees
Jun 12 - Jun 13
Soul Oasis - home on the Chesapeake Bay
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Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Beach
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, (4)
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (29)
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Fridge, microwave, oven, stovetop
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (171)
"Groomsmen stayed here for wedding. Great experience in a beautiful location. Swimming and kayaking right out the back door. Owners were very kind and helpful. Definitely recommend this beautiful spot."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Shewell’s Rambler in the Chesapeake Ranch Estates
View from property
Shewell’s Rambler in the Chesapeake Ranch Estates
9.2 out of 10, Wonderful, (19)
"Nice and super clean. Nice location. We will stay again next time we visit family. "
Shewell’s Rambler in the Chesapeake Ranch Estates
Two bedroom home on charming Solomons Island
Living area
Two bedroom home on charming Solomons Island
9.6 out of 10, Exceptional, (5)
"Beautiful home and great view! I loved the porch swing and deck! The deck is perfect to people watch! There is always an interesting crowd headed to the Tiki bar!! Great stay! Planning on returning soon."
Two bedroom home on charming Solomons Island
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Beach umbrellas, beach towels
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
9.4 out of 10, Exceptional, (9)
"The cabin itself was lovely with a southwestern feel. Very clean when we arrived and met our expectations. The outside space was the best! Even though it was a rainy weekend, we were able to take the kayaks out on the lake during a break in the rain. Unfortunately the weather prohibited us from visiting the beach but the property was close to Solomon's Island where there is plenty of shopping and dining. My only complaint was the mattress in the master bedroom. It felt wore out and we kind of...
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
The Schultz Estate
Outdoor dining
The Schultz Estate
9.6 out of 10, Exceptional, (5)
"This house is great for large groups with plenty of comfortable bedrooms, three bathrooms (note one is only a tub, no shower), and loads of outdoor seating and fire options. This is an old farmhouse, so quirks of an old wooden house on the Eastern shore come with that. Personal bug spray at this property is essential as the mosquitos are very intense. The owner did stop by to give us a lawn spray for them but we did not use it as I am a master naturalist and community garden manager who is...
The Schultz Estate
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, (5)
"We had a lovely stay at The Blue Heron. We had a retreat scheduled with friends that we had to relocate last minute due to snow in western Maryland. We stumbled upon this listing, and the home was perfect for our needs. Plenty of beds, fully stocked kitchen, several rooms and couches for those who wanted to read, others to play games, and others to watch football playoffs on tv. The best part of the house was the dining room table that could seat up to 18 (?). It was nice to be able to not have...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (25)
"We loved the proterty! House was set up with pleanty of room for 4 of us. It was clean and comfortable. Out back was very private. Would definitely stay here again. We had a blast!"
The price is $220
$265 total
includes taxes & fees
Jun 10 - Jun 11
Waterfront Getaway with Dock
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
Exterior
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
10.0 out of 10, Exceptional, (66)
"My family had a wonderful stay at Ivy Cove. We were in town for our niece’s wedding and it was close enough to participate in all family activities but far enough away to be a peaceful haven to relax. The house is beautiful. Beds were very comfortable. We really enjoyed the fire pit and game room. The owner was fantastic. We would absolutely stay again in this amazing home."
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
Quaint Island Getaway
Beach nearby, sun loungers
Quaint Island Getaway
10.0 out of 10, Exceptional, (11)
"This is a charming place, full of really nice interior touches. The location gives you access to some great marshland so you are treated to a daily dose of great bird sightings, including ospreys, red-winged blackbirds, herons and others. The house has everything you need. The only advice I would give - to remind guests to clean off the grill when they are done using it. We had to clean it thoroughly as it had obviously not been cleaned in awhile. I suggest you add that to the short list of...
Quaint Island Getaway
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Smart TV, books
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
9.8 out of 10, Exceptional, (10)
"Just as advertised!!!! Highly recommend!!"
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Cambridge Beach Home on Choptank River w/ Pier!
TV, fireplace, books
Cambridge Beach Home on Choptank River w/ Pier!
10.0 out of 10, Exceptional, (12)
"This place was perfect for our group of 9. Super well equipped. There wasn't a single thing we needed that it didn't have. Lovely!"
Cambridge Beach Home on Choptank River w/ Pier!
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn
Dining
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn
9.6 out of 10, Exceptional, (10)
"Great place! Great location"
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn
Luxury Waterfront Retreat with in ground pool and close to town
Beach/ocean view
Luxury Waterfront Retreat with in ground pool and close to town
10.0 out of 10, Exceptional, (24)
"We stayed here as two families for thanksgiving. The kids (ages 6-15) loved the upstairs. So cozy and the game room was great for family movie night. The kitchen was perfect for all of our cooking. Lots of counter space, drink fridge really helped give extra space in main fridge, kitchen is very well stocked with pots, bakeware, crockpot, blender, and plenty of dinnerware/silverware. The backyard, dock, patio, and awesome view of the sunsets was our afternoon/evening entertainment. We went into...
Luxury Waterfront Retreat with in ground pool and close to town
Historic Hoopersville Getaway on Chesapeake Bay!
Fridge, microwave, stovetop, dishwasher
Historic Hoopersville Getaway on Chesapeake Bay!
9.6 out of 10, Exceptional, (9)
"Our vacation on Chesapeake Bay was wonderful. The house was clean and comfortable. It is an older home, but we loved the character and charm. There is a very large yard for playing, bikes and some board games/puzzles that we enjoyed. The island was very quiet so made for a relaxing vacation. The home came with kayaks, and we had a blast kayaking with our 2 and 4 year old on the ocean. I would highly recommend this home for a big gathering or small family like our trip. We felt so rested after...
Historic Hoopersville Getaway on Chesapeake Bay!
Cozy Catalina Cabin
Fridge, microwave, oven, stovetop
Cozy Catalina Cabin
10.0 out of 10, Exceptional, (9)
"Great stay in southern md. Would do again"
Cozy Catalina Cabin
Don't see what you're looking for?
See all available properties in Wingate
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.

Other types of properties in Wingate you may be interested in

Hyatt Regency Chesapeake Bay
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1010)
"Gorgeous property!"
The price is $187
$254 total
includes taxes & fees
Jul 8 - Jul 9
Hyatt Regency Chesapeake Bay
Comfort Inn & Suites Cambridge
Standard Room, 2 Queen Beds, Non Smoking | Desk, blackout drapes, iron/ironing board, free WiFi
Comfort Inn & Suites Cambridge
2.5 star property
8.2 out of 10, Very Good, (641)
"The hotel was decent. The staff was friendly and the bed sheets were clean. It smells like the previous guest had smoked in the room. The breakfast was ok. "
The price is $109
$121 total
includes taxes & fees
Jun 17 - Jun 18
Comfort Inn & Suites Cambridge
Days Inn & Suites by Wyndham Cambridge
Premium bedding, desk, iron/ironing board, free cribs/infant beds
Days Inn & Suites by Wyndham Cambridge
2.5 star property
6.8 out of 10, (909)
"Much of the hotel was under renovation."
The price is $90
$100 total
includes taxes & fees
Jun 10 - Jun 11
Days Inn & Suites by Wyndham Cambridge
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.

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 $130 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.

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 Schultz Estate : You might want to consider this vacation home rental near Wingate, which offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Wingate?

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

Recent reviews of Wingate properties
Expedia verified reviews

Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5/5 Excellent
"Beautiful and unique property on the bay! Breakfast was delicious! "
A verified traveler stayed at Swanendele Inn at St. Mary's Maryland
Posted 3 days ago
Swanendele Inn at St. Mary's Maryland