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Wingdale Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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 nice, great location in town"
United States
Lisa F.
The price is AU$274
includes taxes & fees
17 Nov - 18 Nov
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.

2. 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 AU$193
includes taxes & fees
28 Nov - 29 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A rustic cabin surrounded by a forest with a stream in the foreground.

3. Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Creek Side Cabin w/ Wood Fired Hot Tub & 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 AU$694
includes taxes & fees
18 Nov - 19 Nov
Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

4. 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 AU$395
includes taxes & fees
27 Nov - 28 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

5. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
7.4 out of 10, Good, (3 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 AU$269
includes taxes & fees
18 Nov - 19 Nov
Welcome to Sweet Abby Rose!
A brick building with a sign reading 'Lobby' in front.

6. 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 AU$132
includes taxes & fees
28 Nov - 29 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
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, (5 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is AU$816
includes taxes & fees
17 Nov - 18 Nov
"Country outside the city " 3 bedrooms 2 full bathrooms
A two-story house with a balcony, surrounded by lush greenery.

8. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"
United States
stephanie a.
The price is AU$778
includes taxes & fees
15 Nov - 16 Nov
Quiet Solitude with Firepit, Electric Stove & Private Deck
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

9. 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 AU$525
includes taxes & fees
18 Nov - 19 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

10. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (20 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is AU$117
includes taxes & fees
8 Dec - 9 Dec
1 King Bed | Non-Smoking, Kitchen, Shower
A modern hotel room with a bed, bedside table, lamp, desk, and window.

11. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (3 reviews)
"We found plenty of space for our small group plus pets. Loved having a private bathroom,it made mornings smooth."
United States
Anonymous traveller
The price is AU$190
includes taxes & fees
15 Nov - 16 Nov
1 King Bed | Non-Smoking
A room with a bed, a couch, a desk with a computer, and various wall decorations.

12. 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 AU$341
includes taxes & fees
17 Nov - 18 Nov
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

13. Little Lake Cabin with Hot Tub and Fire Pit

Little Lake Cabin with Hot Tub and Fire Pit
New Fairfield
10.0 out of 10, Exceptional, (7 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 AU$677
includes taxes & fees
16 Nov - 17 Nov
Little Lake Cabin with Hot Tub and Fire Pit
A white house with a wooden staircase leading to a porch.

14. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is AU$194
includes taxes & fees
2 Dec - 3 Dec
Cozy One Bedroom Apartment Centrally Located in Southbury
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

15. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (9 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is AU$317
includes taxes & fees
16 Nov - 17 Nov
Hudson Valley Farm Getaway- West/Llama Lover Lane
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

16. 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, (31 reviews)
"Everything was just as it was in our past stays. The place was clean, neat and organized very well. Communication with the host was very easy and almost immediate reply."
United States
Albert
The price is AU$332
includes taxes & fees
15 Nov - 16 Nov
Cabin in the heart of the Hudson Valley, Cabin 4
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

17. 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 AU$674
includes taxes & fees
15 Nov - 16 Nov
Sharon Retreat w/ Private Yard
A white house with a steeply pitched roof and a small tower-like structure.

18. 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, (9 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is AU$680
includes taxes & fees
15 Nov - 16 Nov
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

19. 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 place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
The price is AU$405
includes taxes & fees
23 Nov - 24 Nov
Cabin in the Heart of the Hudson Valley, Cabin 1
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
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
The price is AU$540
includes taxes & fees
4 Dec - 5 Dec
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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Find holiday rentals that suit your style

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Top Wingdale Hotel Reviews

A two-story house with a porch, white railings, and a blue door.
Station Inn Pawling

Station Inn Pawling

Station Inn Pawling
Pawling

10/10 Excellent

Great place to stay, very nice room. Close to local attractions like Darryl’s House
Australia
Graeme
Reviewed July 13, 2024
Station Inn Pawling

Find out more about Wingdale

Everything you need to know about Wingdale holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wingdale holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wingdale holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Wingdale holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wingdale. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wingdale holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wingdale holiday rentals we have selected for you start as low as AU$2,100 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wingdale rentals

At Expedia, we put the best Wingdale holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wingdale rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wingdale holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wingdale. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.