Photo by Anna Arsenault

Holiday Homes in Wingdale

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Wingdale

Serene Hudson Valley Escape w/ Pool & Grill
Fridge, microwave, stovetop, dishwasher

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (1)
"An amazing stay in the 4th of July weekend- great place, double pool, giant rooms and everything in, included a patio for chillout, grilling and enjoy weekends with family and friends. Also, owners are nice, really kind and we definitely stay in touch for future escapes"
Serene Hudson Valley Escape w/ Pool & Grill
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

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

9.8 out of 10, Exceptional, (26)
"Perfect for small family stay over for a wedding ! "
The price is AU$547
includes taxes & fees
29 July - 30 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Cozy living room with a fireplace, flat-screen TV, and comfortable seating area.

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

9.2 out of 10, Wonderful, (35)
"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."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Enjoy a peaceful lakeside retreat with a barbecue grill and comfortable seating area.

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

9.0 out of 10, Wonderful, (16)
"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."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room
Relax by the serene pool surrounded by lush greenery and a children's play area.

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

6.0 out of 10, (1)
"Property was very clean and nicely decorated. There isn’t really a living room to hang out. Very difficult for 3 adults to all hang out together. When I booked I was more concerned about the sleeping area so I assumed there was a living room. The guest suite is in the basement of home in a nice neighborhood."
The price is AU$388
includes taxes & fees
30 July - 31 July
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

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

10.0 out of 10, Exceptional, (84)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Modern NY Home w/ Views By Hudson Valley Hiking!
Relax in this stylish living space with a large sofa, matching ottoman, and modern light fixture.

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"
Modern NY Home w/ Views By Hudson Valley Hiking!
Mountain View Getaway
Relax on the deck with a barbecue grill and comfortable seating for six.

Mountain View Getaway

10.0 out of 10, Exceptional, (55)
"Such a magical place…always enjoy our stay. The home is so comfy - the hosts are amazing. "
Mountain View Getaway
Private Annex/Former Artist Studio
Relax on the deck overlooking a lush garden with a tranquil atmosphere.

Private Annex/Former Artist Studio

10.0 out of 10, Exceptional, (51)
"We had a wonderful 3 night stay in the Artist Annex! Everyrhing was jus"
Private Annex/Former Artist Studio
Woodland A-Frame
Spacious living area with a high ceiling, stone accent wall, and kitchen island.

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Stylish Pine Plains Home Near Parks & Hiking!
Enjoy cooking in this fully equipped kitchen with a range, oven, microwave, and sink.

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (14)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Enjoy a formal dining experience with a view of the surrounding forest from the large windows.

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

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
The House In Highland- Secluded Retreat
Enjoy outdoor dining and relaxation on the spacious deck with comfortable seating and a barbecue grill.

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (9)
The House In Highland- Secluded Retreat
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Enjoy serene lakeside views from the dock, where a rowboat and canoe await.

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

10.0 out of 10, Exceptional, (122)
"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."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Relax by the serene lake with a dock, Adirondack chairs, and a small table.

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

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Hickory on Willow Lake
Escape to a serene oasis beneath a triangular gazebo, surrounded by lush greenery and a tranquil hillside setting.

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is AU$952
includes taxes & fees
29 July - 30 July
Hickory on Willow Lake
Spacious Woodbury Home w/ Pool + Hot Tub!
Relax in a warm and inviting space with a hot tub, wicker furniture, and large windows.

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (3)
"Great spot and location, house was clean and enjoyable. Pool needs additional care and cleaning "
Spacious Woodbury Home w/ Pool + Hot Tub!
CT Gate House Goshen CT, Gate House Goshen CT
Step into this charming cabin, featuring a spacious porch and covered seating area amidst lush surroundings.

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (1)
"The property was great and the house was huge even for all 12 of us "
The price is AU$1,037
includes taxes & fees
29 July - 30 July
CT Gate House Goshen CT, Gate House Goshen CT
Twin Cedar Pond: Lovely Farmhouse w/ Sprawling Deck and Therapy Pool
Relax on the spacious deck with picturesque views of the serene lake and lush greenery.

Twin Cedar Pond: Lovely Farmhouse w/ Sprawling Deck and Therapy Pool

10.0 out of 10, Exceptional, (10)
"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."
Twin Cedar Pond: Lovely Farmhouse w/ Sprawling Deck and Therapy Pool
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!
Cozy living space with a comfortable seating area, dining table, and fireplace.

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (9)
"We had a wonderful vacation with our grandchildren and family. The children lived in the water if not kayaking or water boards they were fishing!! Rainy days puzzles were our entertainment the summer house provided everything one wanted or needed. It was a very delightful vacation"
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free