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Holiday Homes in Wingdale

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Wingdale holiday homes

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

1. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is NZ$254
includes taxes & fees
3 Nov - 4 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

2. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is NZ$1,001
includes taxes & fees
3 Nov - 4 Nov
"Country outside the city " 3 bedrooms 2 full bathrooms
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

3. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is NZ$602
includes taxes & fees
3 Nov - 4 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

4. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is NZ$489
includes taxes & fees
22 Oct - 23 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A bedroom with a bed, a dresser, and a window with curtains.

5. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is NZ$1,523
includes taxes & fees
26 Oct - 27 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A multi-story house with a dock and boats, surrounded by dense forest.

6. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
North Cliff House - Private Dock & Sauna
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

7. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (7 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is NZ$1,444
includes taxes & fees
25 Oct - 26 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

8. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is NZ$738
includes taxes & fees
21 Oct - 22 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
An outdoor patio area with a covered seating area, a pool, and potted plants.

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (81 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is NZ$591
includes taxes & fees
28 Oct - 29 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A hot tub in a backyard with a house, trees, and a clear sky.

10. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is NZ$6,189
includes taxes & fees
21 Oct - 22 Oct
Las Flores Villa
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

11. Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is NZ$987
includes taxes & fees
1 Nov - 2 Nov
Hickory on Willow Lake
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

12. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is NZ$738
includes taxes & fees
16 Nov - 17 Nov
Red Cottage - Lakeside Property!
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

13. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is NZ$1,181
includes taxes & fees
25 Oct - 26 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

14. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (12 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is NZ$1,920
includes taxes & fees
21 Oct - 22 Oct
The George is an elegant restored home in the Hudson Valley
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

15. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
United States
Quintina R.
The price is NZ$965
includes taxes & fees
16 Nov - 17 Nov
Chestnut on Willow Lake
A modern kitchen with white cabinets, a large island, and a skylight.

16. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is NZ$2,443
includes taxes & fees
28 Oct - 29 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

17. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is NZ$1,735
includes taxes & fees
21 Oct - 22 Oct
Chic Barn Style * Fireplace * Near Stissing House
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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Top Wingdale Hotel Reviews

The Heartwood

The Heartwood

10/10 Excellent
"Though my stay was brief, it was entirely lovely!! The location was accessible to many of the upstate October/Fall festivities, the Vassar campus and surrounding area were gorgeous with the fall foliage, and the staff at the hotel were incredibly kind and helpful. The rooms were so spacious and the beds were so comfortable!! Highly recommend staying here."
Kate 1-night trip
Posted less than an hour ago
The Heartwood

Find out more about Wingdale

Wingdale Holiday Homes information

Number of reviews
171
Accommodation
252 Holiday Homes
Lowest Price
NZ$254
Highest Price
NZ$6,189