Wingdale Vacation Rentals from ￥16,070: Search Short-Term Rentals

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Vacation Rentals in Wingdale

Enjoy serene lakeside views from the dock, where a rowboat and canoe await.

"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."

Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

"Plenty of room for my family"

￥48,032 total

includes taxes & fees

Jul 20 - Jul 21

Enjoy a peaceful lakeside retreat with a barbecue grill and comfortable seating area.

"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."

Cozy living room with a fireplace, flat-screen TV, and comfortable seating area.

"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."

Enjoy a formal dining experience with a view of the surrounding forest from the large windows.

Relax by the serene pool surrounded by lush greenery and a children's play area.

Enjoy outdoor dining and relaxation on the spacious deck with comfortable seating and a barbecue grill.

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

"The house was super clean and very easy to take care of while we were here. It was perfect for a remote getaway, hiking and just being quiet. "

Relax by the serene lake with a dock, Adirondack chairs, and a small table.

"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"

Relax in this stylish living area with a central sofa, two armchairs, and a balcony offering a view.

"This house was great for our group of 19 people. We went to celebrate my moms birthday and she had the best weekend. The living room is a great place for everyone to hang and the amenities were amazing. We were able to use the hot tub, go in the sauna, play pool/foosball, and it's in a great location. Highly recommend this property and they were also very easy to communicate with. "

Escape to a serene oasis beneath a triangular gazebo, surrounded by lush greenery and a tranquil hillside setting.

"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"

￥89,990 total

includes taxes & fees

Jul 17 - Jul 18

Kitchen area with refrigerator, microwave, and wooden floor.

"Really a nice place. Great for an overnight stop in the Hudson Valley"

￥32,411 total

includes taxes & fees

Jul 14 - Jul 15

Relax in a warm and inviting space with a hot tub, wicker furniture, and large windows.

"We rented this place for the first time for a family gathering. The setting was very private and “country-ish”. For the most part everything listed was present at the place and there were enough sleeping options for our crew. Overall - the owners were nice and fairly responsive but there was a level of disappointment to the care of the property and more importantly the preparedness for our arrival. They said the pool and hot tub were cleaned and ready but the pool was still dirty and the hot tub...

Enjoy a meal or relax with friends on the deck, surrounded by a lush yard and trees.

"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "

￥25,380 total

includes taxes & fees

Jul 15 - Jul 16

Stunning waterfront property with a charming detached house and beautifully maintained garden.

"This beautiful home offered plenty of space for our family of 6 adults and 2 children to enjoy a week together. "

Step into this charming cabin, featuring a spacious porch and covered seating area amidst lush surroundings.

￥113,739 total

includes taxes & fees

Jul 14 - Jul 15

Relax on the spacious deck with picturesque views of the serene lake and lush greenery.

"We had some trouble with our check in process, but the response time to fix it was quick. The hot tub was lovely, and the pool house was so fun for both the adults and the kids. There was an issue with my wife finding old kids applesauce packets behind the couch throw pillow. Other than that it was a great stay. Kids had fun on the swings and hammock."

Host gatherings on the wrap-around porch amidst lush greenery.

"We stayed for a birthday weekend with a few other couples and had a great time. There is plenty of space for everyone to spread out and each 'area' of the house is incredibly comfortable (especially the movie theater). If you need anything there are plenty of stores close by and the area is very safe. Overall, no complaints and would recommend to anyone looking for a getaway."

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Find out more about Wingdale

Search for holiday rentals in Wingdale on Expedia! You can easily find your home rentals, villas, holiday apartments in Wingdale using one of the methods below:

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Look no further and take a look at our great range of rental properties in Wingdale!

Recent reviews of Wingdale properties

5/5 Excellent

"My room was like the picture. "

A verified traveler stayed at Wingate by Wyndham Fishkill

Posted 2 days ago

DoubleTree by Hilton Poughkeepsie Convention Center

5/5 Excellent

Great visit!

"From the time I arrived the stay was perfect. The staff at the desk, the informative way I was checked in…. The cookies ❤️❤️❤️❤️. The room was perfect, loved the shower. Loved the size of the room and the TV. I ate breakfast on the second day. Trinity was fantastic as was the young bus boy, very prompt with the coffee. I will choose Doubletree Hilton every time I can. "

A verified traveler stayed at DoubleTree by Hilton Poughkeepsie Convention Center

Posted 2 days ago

5/5 Excellent

"Great, clean pool, clean rooms, no complaints. One thing to note: there is no elevator to the second floor! So if you have luggage or have walking difficulties or injuries , there’s no way to get on second floor, other than stairs. If hotel is fully booked you also may not have an option to switch to the first level, which is what we had to deal with. Staff helped us with luggage, but there’s no bellman, so that was challenging. Breakfast was also below average, but waffles were good. Need fruit and protein.."

A verified traveler stayed at Quality Inn Poughkeepsie

Posted 5 days ago

Frequently asked questions

Can I find vacation rentals in Wingdale?

Yes, we give you a choice of vacation rentals near well known attractions in Wingdale, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Wingdale?

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!: This Wingdale vacation home rental is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Wingdale?

Choose from 3 Expedia vacation rentals in Wingdale for a memorable vacation.

What’s there to see and do in Wingdale?

Explore the area and family-friendly sights such as SplashDown Beach, or get out into nature at a spot like Lake Waramaug State Park. While here, Dover Veterans Memorial Library and Harlem Valley Golf Club are other places worth a visit.

What’s a vacation rental in Wingdale like?

Vacation rentals are private properties you can stay in for a long or short time in Wingdale. Vacation rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.

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Wingdale Vacation Rentals

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Vacation Rentals in Wingdale

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Serene Hudson Valley Escape w/ Pool & Grill

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Magnificent Lake View

The House In Highland- Secluded Retreat

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Rhinebrook Estate - 8 Bed/8Bath (Sleeps 20)

Hickory on Willow Lake

Cabin in the Heart of the Hudson Valley, Cabin 1

Spacious Woodbury Home w/ Pool + Hot Tub!

New One Bedroom Apartment Centrally Located in Southbury

Spectacular Lake front house

CT Gate House Goshen CT, Gate House Goshen CT

Twin Cedar Pond: Lovely Farmhouse w/ Indoor Pool

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Find out more about Wingdale

Recent reviews of Wingdale properties

Wingate by Wyndham Fishkill

DoubleTree by Hilton Poughkeepsie Convention Center

HYATT house Fishkill/Poughkeepsie

Hampton Inn Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

Hotel Zero Degrees Danbury

Quality Inn Poughkeepsie

La Quinta Inn & Suites by Wyndham Danbury

Hilton Garden Inn Fishkill

Frequently asked questions