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Wingdale Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Wingdale holiday rentals

A covered outdoor area with a wooden deck and a view of a grassy landscape with trees and a distant white building.

1. 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$862
HK$1,614 total
includes taxes & fees
13 Sept - 14 Sept
Hoppy Hill Farm House
Two camping tents set up in a forest with chairs and a wooden platform nearby.

2. 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, (11 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.
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
A living room with a fireplace, two armchairs, a sofa, and a TV.

3. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
The price is HK$1,529
HK$1,970 total
includes taxes & fees
1 Oct - 2 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

4. 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, (1 review)
"Clean and close to activitys"
United States
randall
The price is HK$621
HK$1,231 total
includes taxes & fees
4 Oct - 5 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A covered outdoor kitchen with a grill, bar stools, and a refrigerator stocked with snacks.

5. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
Glamping, family fun, pet friendly
Two tents set up in a forest with a table and chairs in front.

6. 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
Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

7. "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$1,552
HK$4,479 total
includes taxes & fees
15 Sept - 16 Sept
"Country outside the city " 3 bedrooms 2 full bathrooms
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

8. 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$1,444 total
includes taxes & fees
10 Sept - 11 Sept
Welcome to Sweet Abby Rose!
A white house with a wooden staircase leading to a porch.

9. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 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$691
HK$952 total
includes taxes & fees
20 Sept - 21 Sept
Cozy One Bedroom Apartment Centrally Located in Southbury
A white house with a grey roof, a balcony with a blue umbrella, and a visible chimney.

10. 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$1,810 total
includes taxes & fees
15 Sept - 16 Sept
The Perch in the Purchase -- Cozy, unique, and private
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
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,764
HK$3,306 total
includes taxes & fees
23 Sept - 24 Sept
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A brick building with a sign reading 'Lobby' in front.

12. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Nice place to stay"
United States
Anonymous traveller
The price is HK$643
HK$743 total
includes taxes & fees
5 Oct - 6 Oct
1 Queen Bed | Non-Smoking, Kitchen
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

13. 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$1,325
HK$2,191 total
includes taxes & fees
10 Sept - 11 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

14. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.6 out of 10, Excellent, (24 reviews)
"Worst hotel experience I have ever had. Grounds were unkept. No one was at the front desk when I first arrived. Waited 20 minutes for someone to arrive and had to leave for dinner. Came back to find out that they were overbooked."
United States
Glenn
The price is HK$643
HK$727 total
includes taxes & fees
30 Sept - 1 Oct
2 Queen Beds | Non-Smoking, Kitchen
A room with a Yale banner, a white robe hanging on a rack, and a light switch on the wall.

15. 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
The price is HK$3,175
HK$5,646 total
includes taxes & fees
10 Sept - 11 Sept
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A room with a bed, a couch, a desk with a computer, and various wall decorations.

16. 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$1,733
HK$2,311 total
includes taxes & fees
5 Oct - 6 Oct
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A white house with a steeply pitched roof and a small tower-like structure.

17. 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, (6 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$2,509
HK$3,849 total
includes taxes & fees
10 Sept - 11 Sept
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

18. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (16 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,686
HK$2,150 total
includes taxes & fees
10 Sept - 11 Sept
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

19. 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$1,422
HK$1,835 total
includes taxes & fees
14 Sept - 15 Sept
Hudson Valley Farm Getaway- West/Llama Lover Lane
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

20. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,371
HK$3,553 total
includes taxes & fees
10 Sept - 11 Sept
Rustic Cabin in 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

Comfort Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

8/10 Good
"Todo estuvo muy bien, valió la pena viajar hasta halla."
Eury 1-night trip
Posted 2 hours ago
Comfort Inn & Suites Danbury-Bethel

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 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.