Holiday Homes in Wingdale

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Wingdale holiday homes

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, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is NZ$562
includes taxes & fees
8 June - 9 June
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Exterior detail

Upstate 3-bedroom house with hot tub and fire pit in tranquil Fishkill

Upstate 3-bedroom house with hot tub and fire pit in tranquil Fishkill
Fishkill
The price is NZ$649
includes taxes & fees
9 June - 10 June
Upstate 3-bedroom house with hot tub and fire pit in tranquil Fishkill
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 NZ$725
includes taxes & fees
15 June - 16 June
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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 NZ$443
includes taxes & fees
8 June - 9 June
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hair dryer, towels, soap, toilet paper

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 NZ$463
includes taxes & fees
23 June - 24 June
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 NZ$1,193
includes taxes & fees
10 June - 11 June
NEW: Chic Modern Barn Style Home in Fun Area
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 NZ$1,299
includes taxes & fees
15 June - 16 June
Awesome Lake Home with tons of fun!
Smart TV

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
The price is NZ$654
includes taxes & fees
22 June - 23 June
King Bed | Private Parking | Strong WiFi
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)
"Great host"
United States
Lindsey F.
The price is NZ$1,071
includes taxes & fees
9 June - 10 June
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
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 NZ$1,010
includes taxes & fees
9 June - 10 June
"Country outside the city " 3 bedrooms 2 full bathrooms
Property grounds

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is NZ$1,272
includes taxes & fees
9 June - 10 June
Red Cottage - Lakeside Property!
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (4 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 NZ$1,212
includes taxes & fees
8 June - 9 June
Chestnut on Willow Lake
Smart TV

Cozy Escape -Strong Wi-Fi -Prime Location

Cozy Escape -Strong Wi-Fi -Prime Location
Poughkeepsie
6.8 out of 10, (5 reviews)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
United States
Andrea C.
The price is NZ$565
includes taxes & fees
8 June - 9 June
Cozy Escape -Strong Wi-Fi -Prime Location
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 NZ$1,486
includes taxes & fees
8 June - 9 June
Whispering Estate Guest House - A Romantic Countryside Getaway
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.
The price is NZ$1,621
includes taxes & fees
8 June - 9 June
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
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 price is NZ$1,893
includes taxes & fees
8 June - 9 June
The George is an elegant restored home in the Hudson Valley
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.
The price is NZ$2,463
includes taxes & fees
8 June - 9 June
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.
The price is NZ$1,322
includes taxes & fees
8 June - 9 June
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

Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

10/10 Excellent
"Love it here"
Rachel 1-night trip
Posted 2 hours ago
Heritage Hotel, Golf & Conference Center

Find out more about Wingdale

Wingdale Holiday Homes information

Number of reviews
9,626
Accommodation
288 Holiday Homes
Lowest Price
NZ$184
Highest Price
NZ$585