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Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 105 Vacation Homes in Wingate with updated reviews, rates, and availability.

**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, (187)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay
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, (43)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Walk to Dtwn: Waterfront Eastern Shore Townhome!
Pool

Walk to Dtwn: Waterfront Eastern Shore Townhome!

10.0 out of 10, Exceptional, (3)
"We had a wonderful couple of days at this beautifully decorated home! It truly felt like a home away from home. The kitchen was stocked with everything we could possibly need. The location on the harbor was lovely! And walkable to restaurants and playground. It was exactly what we were looking for in our stay!"
Walk to Dtwn: Waterfront Eastern Shore Townhome!
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (42)
"We appreciated the cleanliness of the home and the location was beautiful and convenient to the state/national park, town and Harriet Tubman museum."
The price is SARĀ 863
SARĀ 1,030 total
includes taxes & fees
10 Jun - 11 Jun
Waterfront Getaway with Dock
Stunning secluded Luxury waterfront cottage with private deep water pier!
Exterior

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (75)
"Great location. Spacious and clean. Easy checking in and communicate with owner."
Stunning secluded Luxury waterfront cottage with private deep water pier!
The Blackwater refuge country house on a quiet 12 acres
Property grounds

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (9)
"Very happy with this place, quiet, clean, all good. "
The Blackwater refuge country house on a quiet 12 acres
Chesapeake Bay Paradise 'Bliss on the Bay' in Scotland-Kayak, Relax & Reconnect!
Fridge, microwave, oven, stovetop

Chesapeake Bay Paradise 'Bliss on the Bay' in Scotland-Kayak, Relax & Reconnect!

9.2 out of 10, Wonderful, (10)
"Wow, this stay was everything we could have imagined and more. The house was perfect and super clean. The real sell for me was proximity to a quiet beach! So special, and Trish was beyond an amazing host!"
Chesapeake Bay Paradise 'Bliss on the Bay' in Scotland-Kayak, Relax & Reconnect!
Beautiful Colonial Home on the Choptank River
Lake

Beautiful Colonial Home on the Choptank River

10.0 out of 10, Exceptional, (9)
"We had a lovely long weekend in this house. The house is beautiful. We loved how they combined the old with the new. The space is wonderful. We spent a lot of time on the porch. We ate at the picnic table by the water. The view is great. We loved it all! We look forward to coming back."
Beautiful Colonial Home on the Choptank River
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Interior

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

10.0 out of 10, Exceptional, (12)
"The home is absolutely beautiful and Dina is a great host. My family and I have full intentions of coming back!"
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Luxury on the river, steps to downtown &boat ramp!
Fridge, microwave, oven, stovetop

Luxury on the river, steps to downtown &boat ramp!

10.0 out of 10, Exceptional, (7)
"Stayed for three nights with a few friends with a focus on birding. The house is in a great location for "
The price is SARĀ 1,121
SARĀ 1,968 total
includes taxes & fees
1 Jun - 2 Jun
Luxury on the river, steps to downtown &boat ramp!
Historic Hoopersville Getaway on Chesapeake Bay!
Fridge, microwave, stovetop, dishwasher

Historic Hoopersville Getaway on Chesapeake Bay!

9.6 out of 10, Exceptional, (10)
"I really canā€™t say enough about this place! The house has so much charm! The island is very quiet! Great place to just get away and spend quality time with your family! Canā€™t wait to go back!"
Historic Hoopersville Getaway on Chesapeake Bay!
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Beach towels

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

10.0 out of 10, Exceptional, (77)
"Great property for a family get together. "
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Interior

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9.8 out of 10, Exceptional, (10)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didnā€™t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. Thereā€™s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (163)
"Clean and nice location. Worked perfectly for our visit to the area to spend time with our daughter, son-in-law, and two perfect grandsons. Thank you for sharing your beautiful home and location. "
Waterfront Wildlife Retreat on the Patuxent River
The Schultz Estate
Outdoor dining

The Schultz Estate

8.4 out of 10, Very Good, (15)
"downstairs common rooms were clean and decorated beautifully mosquitoes were a nightmare 5 bedrooms upstairs aka 5 couples had to share 2 bathrooms. one bedroom downstairs had to take a hike across to the other side of the house to use the bathroom which was adjacent from the kitchen despite any deficiencies we made it all work and had a great time"
The Schultz Estate
Luxury Waterfront Retreat with in ground pool and close to town
Miscellaneous

Luxury Waterfront Retreat with in ground pool and close to town

10.0 out of 10, Exceptional, (35)
"Second stay at this amazing rental. Everything was perfect just like the first visit. Gorgeous location, very clean, and all amenities you need. Will definitely be back!"
Luxury Waterfront Retreat with in ground pool and close to town
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Dining

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2.0 star property
9.8 out of 10, Exceptional, (8)
"Great house, attentive host, and a beautiful and quiet setting"
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
18-Acre Waterfront Sanctuary: Peace & Privacy
Aerial view

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy
Fridge, microwave, oven, stovetop

Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

9.4 out of 10, Exceptional, (3)
"Our group really enjoyed the house and the hospitality. There were several nice touches to make us feel welcomed."
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy
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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Other property types in Wingate

Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (24)
"Teresa was awesome. "
The price is SARĀ 521
SARĀ 1,113 total
includes taxes & fees
29 May - 30 May
Soul Oasis - home on the Chesapeake Bay
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, (43)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Waterfront Cottage in Beautiful Hoopers Island
Property grounds

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (70)
"This is a small, sweet, comfortable cottage, and was just perfect for our brief getaway from the hurly-burly. The house is very well equipped, especially the kitchen, so cooking the local seafood was easy. The decor (loved the faux fireplace) was charming and welcoming, down to the live Poinsettia plant on the table when we got there. "
Waterfront Cottage in Beautiful Hoopers Island
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.