Lodging Image

Wingdale Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Wingdale vacation rentals

Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (33 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 ￥15,143
￥20,650 total
includes taxes & fees
Jun 28 - Jun 29
Cozy One Bedroom Apartment Centrally Located in Southbury
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 ￥12,959
￥21,616 total
includes taxes & fees
Jun 29 - Jun 30
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is ￥17,795
￥33,307 total
includes taxes & fees
Jul 13 - Jul 14
Hoppy Hill Farm House
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)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is ￥20,868
￥32,677 total
includes taxes & fees
Jul 2 - Jul 3
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is ￥14,594
￥16,873 total
includes taxes & fees
Jul 24 - Jul 25
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Smart TV

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
The price is ￥15,304
￥56,200 total
includes taxes & fees
Jul 22 - Jul 23
King Bed | Private Parking | Strong WiFi
Lobby

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Great rooms and service,"
United States
Anonymous traveler
The price is ￥14,594
￥16,509 total
includes taxes & fees
Jul 19 - Jul 20
1 King Bed | Non-Smoking, Kitchen, Shower
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, (35 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is ￥27,339
￥45,671 total
includes taxes & fees
Jul 2 - Jul 3
Cabin in the Heart of the Hudson Valley, Cabin 1
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 ￥16,986
￥32,026 total
includes taxes & fees
Jul 13 - Jul 14
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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, (14 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥36,401
￥68,204 total
includes taxes & fees
Jun 29 - Jun 30
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
2 bedrooms, desk, WiFi

King Bed / Private Parking / 300mbps+ WiFi

King Bed / Private Parking / 300mbps+ WiFi
Poughkeepsie
5.0 out of 10, (2 reviews)
"Christina was extremely quick with her responses. My wife and I stayed at this place for the weekend and enjoyed the neighborhood. There's plenty to do, and the apartment is quaint and cozy. The only thing I'd change is adding a curtain to the bathroom window so people can't see you from the outside in."
United States
Jacob E.
The price is ￥14,236
￥53,431 total
includes taxes & fees
Jun 30 - Jul 1
King Bed / Private Parking / 300mbps+ WiFi
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is ￥21,839
￥44,530 total
includes taxes & fees
Jul 2 - Jul 3
Charming 1-bedroom apartment in Carmel with WiFi, AC
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 ￥23,588
￥37,197 total
includes taxes & fees
Jun 30 - Jul 1
The Perch in the Purchase -- Cozy, unique, and private
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, (16 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥26,813
￥34,555 total
includes taxes & fees
Jun 28 - Jun 29
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is ￥24,266
￥44,531 total
includes taxes & fees
Jun 28 - Jun 29
The Tipsy Gypsy - Studio Apartment
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 ￥37,207
￥50,142 total
includes taxes & fees
Jun 30 - Jul 1
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
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)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is ￥29,337
￥38,228 total
includes taxes & fees
Jun 29 - Jun 30
Hudson Valley Farm Getaway- West/Llama Lover Lane
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (68 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is ￥40,041
￥52,285 total
includes taxes & fees
Jun 30 - Jul 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Exterior

Charming Cabin in Fishkill!

Charming Cabin in Fishkill!
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"What a sweet little spot in a gorgeous area - clean, simple, and beautiful. Thanks for a great stay! "
United States
Julia T.
The price is ￥52,498
￥71,787 total
includes taxes & fees
Jun 29 - Jun 30
Charming Cabin in Fishkill!
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 ￥12,959
￥21,616 total
includes taxes & fees
Jun 29 - Jun 30
Glamping, family fun, pet friendly
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wingdale Hotel Reviews

Spark by Hilton Fishkill

Spark by Hilton Fishkill

10/10 Excellent
"Breakfast could have had more choices"
Paul 3-night trip
Posted 7 hours ago
Spark by Hilton Fishkill

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 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 Tymor Park. 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.