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Wingdale Vacation Rentals

Check prices for these dates

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

Our top choices for Wingdale vacation 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
$220 nightly
The price is $249
Oct 29 - Oct 30
Total with taxes and fees
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.
$544 nightly
The price is $616
Oct 28 - Oct 29
Total with taxes and fees
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.
$128 nightly
The price is $144
Nov 3 - Nov 4
Total with taxes and fees
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.
$510 nightly
The price is $577
Nov 2 - Nov 3
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
A bedroom with a bed, a dresser, and a window with curtains.

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.
$767 nightly
The price is $871
Oct 26 - Oct 27
Total with taxes and fees
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.
$510 nightly
The price is $578
Nov 4 - Nov 5
Total with taxes and fees
The Little Lake Cabin with hot tub
A house surrounded by a dense forest with a hammock and a small shed.

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.
$434 nightly
The price is $491
Oct 25 - Oct 26
Total with taxes and fees
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.
$735 nightly
The price is $831
Oct 26 - Oct 27
Total with taxes and fees
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.
$324 nightly
The price is $351
Nov 3 - Nov 4
Total with taxes and fees
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.
$571 nightly
The price is $647
Nov 11 - Nov 12
Total with taxes and fees
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A bathroom with a white sink, toilet, and a mirror. There is a towel on the toilet and a soap dispenser on the sink.

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)
$3,048 nightly
The price is $3,505
Nov 2 - Nov 3
Total with taxes and fees
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
$170 nightly
The price is $184
Oct 22 - Oct 23
Total with taxes and fees
Welcome to Sweet Abby Rose!
A living room with a fireplace, bookshelves, a television, and a comfortable seating area.

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.
$395 nightly
The price is $448
Oct 22 - Oct 23
Total with taxes and fees
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.
$247 nightly
The price is $279
Oct 22 - Oct 23
Total with taxes and fees
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.
$1,107 nightly
The price is $1,253
Oct 26 - Oct 27
Total with taxes and fees
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.
$367 nightly
The price is $429
Oct 22 - Oct 23
Total with taxes and fees
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 traveler
$79 nightly
The price is $92
Nov 2 - Nov 3
Total with taxes and fees
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

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"wonderful stay, exactly what we needed"
James 2-night trip
Posted 2 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

Find out more about Wingdale

Everything you need to know about Wingdale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wingdale vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wingdale vacation 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 low season months. For more hustle and bustle, you may prefer to visit Wingdale in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wingdale rentals

At Expedia, we put the best Wingdale vacation 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 vacation.

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 vacation rentals in Wingdale?

Yes, we give you a choice of vacation rentals near well known attractions in Wingdale, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Wingdale?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of Wingdale offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Wingdale?

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

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 vacation rental in Wingdale like?

Vacation rentals are private properties you can stay in for a long or short time in Wingdale. Vacation rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.