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

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (161)
"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

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!

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

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
9.6 out of 10, Exceptional, (4)
"House was spacious plenty of room, great amenities, and very clean! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

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 didn’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. There’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 Getaway with Dock

10.0 out of 10, Exceptional, (40)
"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 AED 845
AED 1,024 total
includes taxes & fees
10 May - 11 May
Waterfront Getaway with Dock

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"We had a great time. Private beach, spacious house, kayaks!"
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Direct waterfront access to the Chesapeake Bay with pool and hottub

10.0 out of 10, Exceptional, (7)
"Absolutely beautiful property, super clean, stocked with everything you could ever need, great customer service. We’ll definitely be back and for a longer stay."
Direct waterfront access to the Chesapeake Bay with pool and hottub

Luxury Waterfront Retreat with in ground pool and close to town

10.0 out of 10, Exceptional, (35)
"Beautiful house and location to getaway with peace and quiet. Still within 5-10 minutes of anything you need including downtown Cambridge. WillDefinitely come Back!"
Luxury Waterfront Retreat with in ground pool and close to town

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

10.0 out of 10, Exceptional, (5)
"Stayed for three nights with a few friends with a focus on birding. The house is in a great location for "
The price is AED 1,098
AED 1,931 total
includes taxes & fees
8 May - 9 May
Luxury on the river, steps to downtown &boat ramp!

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

**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**

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (74)
"Great location. Spacious and clean. Easy checking in and communicate with owner."
Stunning secluded Luxury waterfront cottage with private deep water pier!

Sunrise Views: Waterfront Lusby Home w/ Deck!

9.6 out of 10, Exceptional, (10)
"The house was lovely and clean. Loved the location right on the water. Sunrises were spectacular. We would definitely rent this house again. "
Sunrise Views: Waterfront Lusby Home w/ Deck!

4-BR Waterfront Turret Home

2.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is AED 2,020
AED 3,659 total
includes taxes & fees
12 May - 13 May
4-BR Waterfront Turret Home

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

8.0 out of 10, Very Good, (4)
"Spacious, orderly interior, lovely setting, great amenities: kayaks, fire pit, creek feeds into Chop tank, close to Saint Michaels and Secretary.Big bedrooms with new comfy beds, plenty of bathrooms and showers.Just a lovely place and excellent communication from host."
The price is AED 1,282
AED 2,437 total
includes taxes & fees
8 May - 9 May
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Bay Views & Fire Pit: Taylor’s Island Retreat

10.0 out of 10, Exceptional, (12)
"We really enjoyed our stay, and our dog was able to get into the water with the ramp that they have built there."
Bay Views & Fire Pit: Taylor’s Island Retreat

New Island Home on the Chesapeake Bay Sunsets

10.0 out of 10, Exceptional, (6)
"A well stocked and well kept house on the water with fantastic sunset views, a big yard for games, and a game room and fire pit for the night. "
New Island Home on the Chesapeake Bay Sunsets

Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

9.0 out of 10, Wonderful, (16)
"My family enjoyed our stay over Thanksgiving. Three generations with different needs and the house accommodated us well."
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

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

2.0 star property
9.8 out of 10, Exceptional, (6)
"Great house, attentive host, and a beautiful and quiet setting"
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
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

10.0 out of 10, Exceptional, (22)
"Perfect family get away with a great view!"
The price is AED 511
AED 1,094 total
includes taxes & fees
11 May - 12 May
Soul Oasis - home on the Chesapeake Bay

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (69)
"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

**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**
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.