Wingate Vacation Rentals

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Vacation Rentals in Wingate

Outdoor dining
The Schultz Estate
10.0 out of 10, Exceptional, (4)
"Had a great stay! Beautiful location! House was clean roomy, overall had a great time! The only thing I would say is work on the doors closing. In restrooms."
The Schultz Estate
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (53)
"Had a wonderful time really enjoyed the use of the dock the house was perfect had everything you could of possibly needed definitely will be back!"
Waterfront Cottage in Beautiful Hoopers Island
Exterior
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 CA $177
CA $394 total
includes taxes & fees
Jun 5 - Jun 6
Soul Oasis - home on the Chesapeake Bay
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Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (28)
"The house was great and nice area!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Beach nearby, sun loungers
Quaint Island Getaway
10.0 out of 10, Exceptional, (9)
"This was a very nice well kept home in historical Deal Island. This home was very well equipped with everything you need to make your stay comfortable. Which was really appreciated because there is no stores really close. I would definitely stay here again."
Quaint Island Getaway
Fridge, microwave, oven, stovetop
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (170)
"We spent the weekend relaxing in the outdoors with family. We kayaked, had an outdoor fire and enjoyed the wildlife that floated or flew by."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Beach
Belle of the Chesapeake Bay
10.0 out of 10, Exceptional, (2)
"The property was very clean and nicely appointed."
Belle of the Chesapeake Bay
Property grounds
El Camino
10.0 out of 10, Exceptional, (23)
"We wanted a quiet break away from it all. The cabin is clean and comfy. Located by a lovely creek. Sat on the porch and listened to the birds milling about in the trees. We loved it."
El Camino
Property grounds
Waterfront Lusby Home w/ Deck & Stunning Views!
10.0 out of 10, Exceptional, (1)
Waterfront Lusby Home w/ Deck & Stunning Views!
TV, fireplace, books
Cambridge Beach Home on Choptank River w/ Pier!
10.0 out of 10, Exceptional, (11)
"We are a group of mid 50s ladies that went to Jr High and High School together. We do an annual "girls" trip and usually head to Deep Creek Lake or Ocean City where some of us own second homes. We decided to switch things up this year and found this amazing rental. From the moment we walked in the door and saw the lovely note and goodies that were left for us - to the beautiful decor and gorgeous bedrooms. There was absolutely nothing missed in this rental. Kitchen fully stocked AND MORE!!! The...
Cambridge Beach Home on Choptank River w/ Pier!
Fridge, microwave, oven, stovetop
Tidal Serenity- Remote Waterfront Home with dock
10.0 out of 10, Exceptional, (15)
"Your Tidal Serenity home is a dream come true! Our stay was an incredible nature experience. The house was clean and comfy and the dock was the perfect centerpiece for adventure and fun. We kayaked, crabbed, fished and spotted a TON of amazing birds. We visited Blackwater Bakery in Cambridge, Emily’s Farm, Blackwater National Refuge and Harriet Tubman’s Underground Railroad National Park and mostly-hung around the property exploring Taylor’s island on bike and foot. We hope to visit...
Tidal Serenity- Remote Waterfront Home with dock
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
Beach
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, (4)
"The home is nicely decorated and clean. The host went above and beyond to help with anything we needed. Would definitely recommend to stay here."
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Exterior
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
10.0 out of 10, Exceptional, (42)
"My husband and I loved our visit to Sunrise Cottage! Everything was perfect and we can't wait to return."
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
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 CA $299
CA $364 total
includes taxes & fees
May 28 - May 29
Waterfront Getaway with Dock
Interior
Hays Beach House - Hot Tub - Private Beach
10.0 out of 10, Exceptional, (1)
"This is our 16th year vacationing at Hay Beach, but our first time staying at this property. The house is very confrontable and the layout is great, plenty of room for our family, 3 couples. The second level deck was the hangout, beautiful views of the sun rises with morning coffee, watching large pods of dolphins swimming 30 yards off the beach, eagles flying overhead and cocktails every evening. The guys fished from kayaks while the girls laid in the sun on the deck every day ... great...
Hays Beach House - Hot Tub - Private Beach
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!
Fridge, microwave, stovetop, dishwasher
Waterfront Taylor’s Island Rental w/ Private Dock!
10.0 out of 10, Exceptional, (6)
"This was a great spot to come and visit. The dock gave the ability to crab and fish whenever. The house and view of the water were amazing. The only downfall for us was the amount of jelly fish so we did not get in the water much. We did bring our boat and launched it right down the road. We are out at the local restaurants and the community was welcoming. We drove around and saw the Harriet Tubman Underground Railroad and visited Cambridge many times."
Waterfront Taylor’s Island Rental w/ Private Dock!
On the beach
Waterfront Scotland Beach Retreat w/Private Beach!
10.0 out of 10, Exceptional, (35)
"Overall it was a great experience. The house is huge, there are 2 living rooms, plenty of bathrooms for the amount of beds that are there. The views were amazing. There were a few things we didn’t have access too only because we stayed during the off season and one thing that we were told we would have access too but after we checked in we’re told it was under renovation; the bocce ball area. Overall a great stay. Not a lot to do in the area during off season but I could see it being an amazing...
Waterfront Scotland Beach Retreat w/Private Beach!
On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (45)
"My husband and I have been to this cottage once before. It's our secret getaway. It has everything you need plus the beach is just a few feet away. You can't find another place like this one!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
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

Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1002)
"Gorgeous property. Beautiful views. Well maintained and kept clean. The bed was the best lullaby ever. I slept ever so soundly. Breakfast was bountiful and delicious. The young lady that checked us in was on the surly side and could use some professional development on friendliness and hospitality for people of all cultures. But, the gentleman from Ghana that check me out made up for what she lacked and redeemed my experience. I would definitely stay again. "
The price is CA $244
CA $334 total
includes taxes & fees
May 22 - May 23
Hyatt Regency Chesapeake Bay
Exterior
Holiday Inn Express Cambridge, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (618)
"Excellent staff and facility!"
The price is CA $162
CA $180 total
includes taxes & fees
Jun 2 - Jun 3
Holiday Inn Express Cambridge, an IHG Hotel
Standard Room, 2 Queen Beds, Non Smoking
Comfort Inn & Suites Cambridge
2.5 star property
8.2 out of 10, Very good, (634)
"Everything was great "
The price is CA $133
CA $148 total
includes taxes & fees
May 28 - May 29
Comfort Inn & Suites 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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Wingate. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 : Visitors like this Wingate vacation home rental. It 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