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Check prices for these dates

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

Our top choices for Wingdale vacation 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 ￥10,676
￥22,717 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥31,482
￥91,301 total
includes taxes & fees
Nov 2 - Nov 3
"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 ￥26,354
￥55,492 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥26,731
￥44,196 total
includes taxes & fees
Oct 30 - Oct 31
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 ￥83,039
￥137,964 total
includes taxes & fees
Oct 27 - Oct 28
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A covered outdoor area with a view of a lake, stone steps, and a grill.

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.
The price is ￥57,231
￥199,705 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥63,268
￥132,947 total
includes taxes & fees
Oct 27 - Oct 28
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
9.8 out of 10, Exceptional, (6 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 ￥25,410
￥67,925 total
includes taxes & fees
Oct 25 - Oct 26
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)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is ￥41,351
￥54,218 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥427,059
￥554,383 total
includes taxes & fees
Oct 23 - Oct 24
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 ￥60,895
￥84,970 total
includes taxes & fees
Nov 21 - Nov 22
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 ￥43,497
￥65,049 total
includes taxes & fees
Nov 21 - Nov 22
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 ￥71,177
￥108,432 total
includes taxes & fees
Oct 27 - Oct 28
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 ￥113,882
￥175,352 total
includes taxes & fees
Oct 23 - Oct 24
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 ￥60,895
￥84,970 total
includes taxes & fees
Nov 21 - Nov 22
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 ￥140,771
￥232,968 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥44,398
￥129,287 total
includes taxes & fees
Nov 4 - Nov 5
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

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

8/10 Good
"Our room was very clean! Breakfast was great with many choices. My only complaint was the coffee/hot water was not made fresh and hot. Most times it was luke warm."
Sandra 2-night trip
Posted 1 hour ago
Hampton Inn & Suites Poughkeepsie

Find out more about Wingdale

Wingdale Vacation Homes information

Number of reviews
172
Accommodation
259 Vacation Homes
Lowest Price
￥22,717
Highest Price
￥554,383