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Wingdale Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Wingdale holiday rentals

Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
The price is HK$863
HK$1,614 total
includes taxes & fees
6 Aug - 7 Aug
Hoppy Hill Farm House
Property grounds

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (8 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is HK$628
HK$1,048 total
includes taxes & fees
27 Jul - 28 Jul
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Internet, bed sheets

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is HK$784
HK$1,445 total
includes taxes & fees
8 Aug - 9 Aug
Welcome to Sweet Abby Rose!
Smart TV, fireplace, books

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (19 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is HK$1,300
HK$1,675 total
includes taxes & fees
27 Jul - 28 Jul
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Outdoor dining

Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
The price is HK$628
HK$1,048 total
includes taxes & fees
27 Jul - 28 Jul
Glamping, family fun, pet friendly
Property grounds

Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly

Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Fun place with a variety of activities including hot tub, miniature golf, corn bag toss, etc. "
United States
Tania
The price is HK$882
HK$1,335 total
includes taxes & fees
7 Aug - 8 Aug
Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
Interior

Architect-Designed Dome on Private 7-Acre Retreat

Architect-Designed Dome on Private 7-Acre Retreat
Dover Plains
The price is HK$1,941
HK$3,864 total
includes taxes & fees
26 Jul - 27 Jul
Architect-Designed Dome on Private 7-Acre Retreat
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 HK$823
HK$1,552 total
includes taxes & fees
29 Jul - 30 Jul
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Exterior

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is HK$704
HK$814 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Lobby

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is HK$783
HK$886 total
includes taxes & fees
29 Jul - 30 Jul
1 King Bed | Non-Smoking, Kitchen, Shower
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, (17 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,835
HK$3,391 total
includes taxes & fees
28 Jul - 29 Jul
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (34 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is HK$762
HK$1,034 total
includes taxes & fees
24 Aug - 25 Aug
Cozy One Bedroom Apartment Centrally Located in Southbury
Coffee/tea maker, fridge, microwave, oven

"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 HK$1,912
HK$4,940 total
includes taxes & fees
23 Aug - 24 Aug
"Country outside the city " 3 bedrooms 2 full bathrooms
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is HK$1,011
HK$1,575 total
includes taxes & fees
29 Jul - 30 Jul
Cabin in the heart of the Hudson Valley, Cabin 4
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 HK$1,905
HK$2,558 total
includes taxes & fees
29 Jul - 30 Jul
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is HK$1,176
HK$2,158 total
includes taxes & fees
26 Jul - 27 Jul
The Tipsy Gypsy - Studio Apartment
Property grounds

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (3 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Outdoor dining

The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$1,143
HK$1,811 total
includes taxes & fees
9 Aug - 10 Aug
The Perch in the Purchase -- Cozy, unique, and private
Property grounds

Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is HK$1,351
HK$1,767 total
includes taxes & fees
26 Jul - 27 Jul
Hudson Valley Farm Getaway- West/Llama Lover Lane
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is HK$1,325
HK$2,140 total
includes taxes & fees
23 Aug - 24 Aug
Cabin in the Heart of the Hudson Valley, Cabin 1
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

Ethan Allen Hotel

Ethan Allen Hotel

10/10 Excellent
"I have stayed a couple times this year already and each time I've had a very relaxing stay. The staff have been helpful every time I needed Assistance or how to question. I stay on my own as a short relaxing getaway and found the bed to be very comfortable and the entire property very clean."
Teresa 1-night trip
Posted 1 hour ago
Ethan Allen Hotel

Find out more about Wingdale

Search for holiday rentals in Wingdale on Expedia! You can easily find your home rentals, villas, holiday apartments in Wingdale using one of the methods below:

  • View our selection of featured holiday rentals in Wingdale
  • Use the map to find apartments and other holiday homes in the Wingdale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wingdale while they last

Look no further and take a look at our great range of rental properties in Wingdale!

Frequently asked questions

Can I find holiday rentals in Wingdale?

Yes, there are holiday rentals close to the most popular sights in Wingdale, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Wingdale has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Wingdale offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and an electric kettle, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Wingdale?

Choose from 3 Expedia holiday rentals in Wingdale for a memorable holiday.

What’s there to see and do in Wingdale?

Explore the area and family-friendly sights such as SplashDown Beach, or get out into nature at a spot like Lake Waramaug State Park. While here, Dover Veterans Memorial Library and Harlem Valley Golf Club are other places worth a visit.

What’s a holiday rental in Wingdale like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wingdale. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.