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Wingdale Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Wingdale holiday rentals

A living room with a fireplace, two armchairs, a sofa, and a TV.

1. 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, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is HK$1,371
HK$1,765 total
includes taxes & fees
10 Nov - 11 Nov
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A rustic cabin surrounded by a forest with a stream in the foreground.

2. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is HK$2,446
HK$4,379 total
includes taxes & fees
3 Nov - 4 Nov
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

3. 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
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is HK$529
HK$1,126 total
includes taxes & fees
3 Nov - 4 Nov
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.

4. "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$1,560
HK$4,524 total
includes taxes & fees
2 Nov - 3 Nov
"Country outside the city " 3 bedrooms 2 full bathrooms
A living room with a white sectional sofa, a dining area with a wooden table and chairs, and a staircase leading to an upper level.

5. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is HK$4,114
HK$6,828 total
includes taxes & fees
26 Oct - 27 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

6. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (6 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is HK$2,676
HK$4,721 total
includes taxes & fees
3 Nov - 4 Nov
The Little Lake Cabin with hot tub
A cozy cabin interior with a wooden ceiling, a fireplace, a sofa, a chair, and a dining table.

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

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
9.6 out of 10, Exceptional, (4 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
A white house with a steeply pitched roof and a small tower-like structure.

8. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.8 out of 10, Exceptional, (8 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is HK$2,510
HK$3,850 total
includes taxes & fees
25 Oct - 26 Oct
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A wooden deck with a lounge chair and a table, a small wooden house with a door and windows, and a wooden fence.

9. Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
9.0 out of 10, Wonderful, (13 reviews)
"Perfect little getaway, adorable space and wonderfully accommodating hosts."
United States
Susan
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

10. 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, (7 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 HK$3,135
HK$6,587 total
includes taxes & fees
3 Nov - 4 Nov
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

11. 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
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,306
HK$2,750 total
includes taxes & fees
3 Nov - 4 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

12. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is HK$2,880
HK$4,934 total
includes taxes & fees
10 Nov - 11 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Interior

13. Hudson Valley Duplex: Hike, Sip + Explore!

Hudson Valley Duplex: Hike, Sip + Explore!
3.0 star property
Highland
Hudson Valley Duplex: Hike, Sip + Explore!
A hot tub in a backyard with a house, trees, and a clear sky.

14. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is HK$21,159
HK$27,468 total
includes taxes & fees
27 Oct - 28 Oct
Las Flores Villa
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

15. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
The price is HK$784
HK$1,452 total
includes taxes & fees
28 Oct - 29 Oct
Welcome to Sweet Abby Rose!
A two-story house with a well-maintained lawn and mature trees.

16. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is HK$1,569
HK$3,510 total
includes taxes & fees
25 Oct - 26 Oct
Sharon Retreat w/ Private Yard
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

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

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is HK$1,324
HK$2,207 total
includes taxes & fees
31 Oct - 1 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A covered outdoor area with a view of a lake, stone steps, and a grill.

18. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is HK$2,447
HK$9,393 total
includes taxes & fees
25 Oct - 26 Oct
North Cliff House - Private Dock & Sauna
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

19. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.8 out of 10, Exceptional, (6 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 HK$1,259
HK$3,365 total
includes taxes & fees
25 Oct - 26 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A brick building with a sign reading 'Lobby' in front.

20. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is HK$620
HK$716 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
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

8/10 Good
"Nice hotel"
Sharon 1-night trip
Posted less than an 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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Wingdale offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, 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 Whaley Lake. 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.