Wingate Holiday Rentals

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Find properties with these dates

Tonight
May 3 - May 4
Tomorrow
May 4 - May 5
This weekend
May 3 - May 5

Holiday Rentals in Wingate

Waterfront Cottage in Beautiful Hoopers Island
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (52)
"A small house, well situated overlooking the waterfront, with a private pier. House interior was very clean and tidy!"
Waterfront Cottage in Beautiful Hoopers Island
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, (28)
"The house was great and nice area!"
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, (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**
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Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (25)
"Three of us stayed overnight on a girl's weekend visit to Blackwater. This property is beautiful! Sunrise over the water was amazing. The house was spotless, stocked with everything you need right down to shower products. The furniture is very comfortable, beds are as well. We didn't get to use the screened porch as it was too chilly, but it will be great in warmer weather. The chickens had a lot to say in the morning, so I felt obligated to stop and visit for a bit. Will definitely stay here...
The price is AU$404
includes taxes & fees
3 June - 4 June
Waterfront Getaway with Dock
Waterfront Scotland Beach Retreat w/Private Beach!
On the beach
Waterfront Scotland Beach Retreat w/Private Beach!
10.0 out of 10, Exceptional, (34)
"We enjoyed our stay at this beautiful home. The property is very clean and the owner's have spent a great deal of attention to detail and design. The location is quiet and the views of the bay are spectacular. Our final night included a beautiful starry sky filled with views of the milky way and shooting stars."
Waterfront Scotland Beach Retreat w/Private Beach!
Waterfront Lusby Home w/ Deck & Stunning Views!
Property grounds
Waterfront Lusby Home w/ Deck & Stunning Views!
10.0 out of 10, Exceptional, (1)
Waterfront Lusby Home w/ Deck & Stunning Views!
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, (64)
"This cottage was everything the listing said and so much more. This was our first time to the area and our favorite thing about the entire trip was the cottage. Beautifully renovated, it had everything. We got a lot of rain and enjoyed sitting on the peaceful porch listening to the rain and the birds overlooking the creek. On Saturday the sun came out and the kids were able to fish, kayak, and roast marshmallows around the large fire pit. Inside, the cottage was full of entertainment. Arcade...
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
Waterfront Taylor’s Island Rental w/ Private Dock!
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!
El Camino
Property grounds
El Camino
10.0 out of 10, Exceptional, (22)
"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
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, (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!
Tidal Serenity- Remote Waterfront Home with dock
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
Belle of the Chesapeake Bay
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
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Beach
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, (3)
"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
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
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.
Quaint Island Getaway
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
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, (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.
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
Pool
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
9.8 out of 10, Exceptional, (116)
"Great house close to the lodge!"
The price is AU$1,036
includes taxes & fees
8 May - 9 May
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (66)
"What a beautiful property! We did a quick couples getaway and couldn’t have had a nicer weekend. The house is a beautiful, wraparound porch country home. Floorplan was really well designed and the decor was spot on. Looking forward to coming back next fall as well!"
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Beach umbrellas, beach towels
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
9.6 out of 10, Exceptional, (7)
"Stunning view, wonderful range of birds in surrounding trees, dawn and dusk visits from deer. House fully furnished. Owner responsive to several queries and provided new toaster. Close enough to shopping with car. "
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn
Interior
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn
9.6 out of 10, Exceptional, (9)
"This is our second time staying at this property and it is perfect. Great location, super clean, excellent communication with property owners. Looking forward to our next visit. A perfect home for a visit to the Cambridge area."
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn
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, pool umbrellas, pool loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1002)
"This was our 6 time visiting the resort. We love everything about the place. The only concern we have is the parking. We have 2 sons with Down Syndrome, so it would be nice if there was handica parking a little closer to the hotel."
The price is AU$336
includes taxes & fees
28 May - 29 May
Hyatt Regency Chesapeake Bay
Holiday Inn Express Cambridge, an IHG Hotel
Exterior
Holiday Inn Express Cambridge, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (610)
"Staff was very pleasant, enjoyed breakfast and room was clean…"
The price is AU$223
includes taxes & fees
14 May - 15 May
Holiday Inn Express Cambridge, an IHG Hotel
Comfort Inn & Suites Cambridge
Standard Room, 2 Queen Beds, Non Smoking
Comfort Inn & Suites Cambridge
2.5 star property
8.2 out of 10, Very good, (628)
"Quiet, clean, safe. Will stay here again! Great front desk service."
The price is AU$166
includes taxes & fees
12 May - 13 May
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.

Everything you need to know about Wingate holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wingate holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wingate holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wingate holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wingate holiday rentals we have selected for you start as low as AU$404 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wingate rentals

At Expedia, we put the best Wingate holiday 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 holiday.

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 holiday rental in Wingate?

Yes, there are holiday rentals close to the most popular sights in Wingate, or you can select a more secluded option if you're looking for a relaxing stay. Wingate is known for its restaurants.

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 wider area.

What are holiday rentals like in Wingate?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wingate. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.

Recent reviews of Wingate properties
Expedia verified reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

5/5 Excellent
"This was our 6 time visiting the resort. We love everything about the place. The only concern we have is the parking. We have 2 sons with Down Syndrome, so it would be nice if there was handica parking a little closer to the hotel."
A verified traveller stayed at Hyatt Regency Chesapeake Bay
Posted 2 days ago
Hyatt Regency Chesapeake Bay