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Holiday Homes in Wingdale
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Our top choices for Wingdale holiday homes
Holiday Home in Goshen
CT Gate House Goshen CT, Gate House Goshen CT9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
Ryan L.
The price is AU$937
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Holmes
"Country outside the city " 3 bedrooms 2 full bathrooms9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
pamela w.
The price is AU$828
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Carmel Hamlet
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
Hannah P.
The price is AU$536
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Home in Hopewell Junction
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
Esther P.
The price is AU$393
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Home in New Fairfield
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake10.0 out of 10, Exceptional, (16)
"Great location and condition. Roome enough for everyone."
Christopher H.
Holiday Home in Poughkeepsie
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY10.0 out of 10, Exceptional, (2)
"Great host"
Lindsey F.
The price is AU$914
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Fishkill
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo9.4 out of 10, Exceptional, (52)
"Quiet, clean and comfortable! Great stay!"
Joseph G.
The price is AU$477
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Poughkeepsie
Cozy Escape -Strong Wi-Fi -Prime Location6.8 out of 10, (5)
"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."
Andrea C.
The price is AU$479
includes taxes & fees
21 Jan - 22 Jan 2026
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.
Top Wingdale Hotel Reviews
Hampton Inn Danbury
10/10 Excellent
Find out more about Wingdale
Wingdale Holiday Homes information
Number of reviews | 144 |
|---|---|
Accommodation | 279 Holiday Homes |
Lowest Price | AU$393 |
Highest Price | AU$1,665 |
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