A weathered window with a view of trees and a building in the background.

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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
The price is £109
includes taxes & fees
1 Sept - 2 Sept
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 £445
includes taxes & fees
8 Sept - 9 Sept
"Country outside the city " 3 bedrooms 2 full bathrooms
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

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

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is £151
includes taxes & fees
30 Aug - 31 Aug
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A room with a bed, a couch, a desk with a computer, and various wall decorations.

4. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is £215
includes taxes & fees
14 Sept - 15 Sept
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

5. 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
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is £322
includes taxes & fees
8 Sept - 9 Sept
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

6. 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, (6 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 £622
includes taxes & fees
2 Sept - 3 Sept
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
An outdoor patio area with a covered seating area, a pool, and potted plants.

7. 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, (74 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is £247
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A patio with a round table and chairs, overlooking a body of water and a forested area during sunset.

8. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (59 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
The price is £1,287
includes taxes & fees
17 Sept - 18 Sept
Candlewood Lake Retreat with Private Dock
A modern kitchen with white cabinets, a built-in toaster, a blender, and a window with a view of trees.

9. Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is £366
includes taxes & fees
31 Aug - 1 Sept
Amazing 3-bedroom house with AC in adorable Highland
A spacious living room with a foosball table, a large flat-screen TV, and a fireplace.

10. Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
The price is £771
includes taxes & fees
31 Aug - 1 Sept
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

11. 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 £399
includes taxes & fees
9 Sept - 10 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

12. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is £522
includes taxes & fees
31 Aug - 1 Sept
Chestnut on Willow Lake

13. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is £514
includes taxes & fees
31 Aug - 1 Sept
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

14. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
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 £549
includes taxes & fees
22 Sept - 23 Sept
NEW: Chic Modern Barn Style Home in Fun Area
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

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

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (9 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 £818
includes taxes & fees
30 Aug - 31 Aug
The George is an elegant restored home in the Hudson Valley
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)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is £1,067
includes taxes & fees
31 Aug - 1 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

17. 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 £577
includes taxes & fees
31 Aug - 1 Sept
Hickory on Willow Lake
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

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent
"Nice staff, quick checking in & out, clean room, good location, restaurant had good food."
Amanda 1-night trip
Posted 4 hours ago
DoubleTree by Hilton Poughkeepsie Convention Center

Find out more about Wingdale

Wingdale Holiday Homes information

Number of reviews
217
Accommodation
261 Holiday Homes
Lowest Price
£109
Highest Price
£1,287