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Holiday Homes in Wingdale

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Wingdale holiday homes

TV, fireplace

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, (14 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is €376
includes taxes & fees
29 Jun - 30 Jun
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining

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, (68 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is €284
includes taxes & fees
30 Jun - 1 Jul
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Exterior

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)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is €178
includes taxes & fees
29 Jun - 30 Jun
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Smart TV

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
The price is €293
includes taxes & fees
29 Jun - 30 Jun
King Bed | Private Parking | Strong WiFi
Interior

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 €267
includes taxes & fees
30 Jun - 1 Jul
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is €619
includes taxes & fees
30 Jun - 1 Jul
NEW: Chic Modern Barn Style Home in Fun Area
Interior

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, (4 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Cookware/dishes/utensils

Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (9 reviews)
"Great spot "
United States
Mike P.
The price is €678
includes taxes & fees
12 Jul - 13 Jul
Awesome Lake Home with tons of fun!
Interior

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 €750
includes taxes & fees
2 Jul - 3 Jul
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Property grounds

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is €648
includes taxes & fees
28 Jul - 29 Jul
Red Cottage - Lakeside Property!
Dining

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, (7 reviews)
"This our 3rd stay at the property and once again we thoroughly enjoyed the house and the grounds. We had an opportunity to enjoy horseback riding on site and would definitely recommend that to any visitors. The hosts were very kind and hospitable. "
United States
Eric L.
The George is an elegant restored home in the Hudson Valley
Fridge, microwave, oven, stovetop

"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 €538
includes taxes & fees
8 Jul - 9 Jul
"Country outside the city " 3 bedrooms 2 full bathrooms
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (5 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 €621
includes taxes & fees
29 Jun - 30 Jun
Chestnut on Willow Lake
Smart TV, fireplace, video games, DVD player

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, (20 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.
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is €788
includes taxes & fees
29 Jun - 30 Jun
Whispering Estate Guest House - A Romantic Countryside Getaway
Dining

Luxe Mountain Getaway on Private Rd Near Rhinebeck

Luxe Mountain Getaway on Private Rd Near Rhinebeck
Hyde Park
Luxe Mountain Getaway on Private Rd Near Rhinebeck
Fridge, microwave, oven, stovetop

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, (13 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.
A Country Lodge Straight Out of the Pages of a Great Novel
Exterior

Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (5 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
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

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

10/10 Excellent
"The hotel was excellent. The bedroom and bathroom were large, nicely decorated and very clean. The grounds were well maintained and the outside sitting area was very inviting."
Stephen 1-night trip
Posted 1 hour ago
Hotel Zero Degrees Danbury

Find out more about Wingdale

Wingdale Holiday Homes information

Number of reviews
8,094
Accommodation
276 Holiday Homes
Lowest Price
€83
Highest Price
€327