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
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Wingdale vacation rentals

Smart TV

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
The price is SAR 318
SAR 1,260 total
includes taxes & fees
22 Jun - 23 Jun
King Bed | Private Parking | Strong WiFi
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 SAR 413
SAR 773 total
includes taxes & fees
22 Jun - 23 Jun
Hoppy Hill Farm House
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is SAR 634
SAR 1,038 total
includes taxes & fees
22 Jun - 23 Jun
Cabin in the heart of the Hudson Valley, Cabin 3
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, (34 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is SAR 634
SAR 1,038 total
includes taxes & fees
22 Jun - 23 Jun
Cabin in the Heart of the Hudson Valley, Cabin 1
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 SAR 301
SAR 502 total
includes taxes & fees
29 Jun - 30 Jun
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Exterior

2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (19 reviews)
"great place tostay"
United States
Anonymous traveler
The price is SAR 413
SAR 477 total
includes taxes & fees
28 Jun - 29 Jun
2 Full Beds | Non-Smoking, Kitchen
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 SAR 338
SAR 382 total
includes taxes & fees
12 Jul - 13 Jul
1 King Bed | Non-Smoking, Kitchen, Shower
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 SAR 394
SAR 743 total
includes taxes & fees
23 Jun - 24 Jun
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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.
King Bed / Private Parking / 300mbps+ WiFi
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 SAR 547
SAR 863 total
includes taxes & fees
22 Jun - 23 Jun
The Perch in the Purchase -- Cozy, unique, and private
1 bedroom, WiFi

King Bed Private Parking Fast Internet

King Bed Private Parking Fast Internet
Poughkeepsie
King Bed Private Parking Fast Internet
Shower, towels, soap, toilet paper

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 SAR 507
SAR 1,021 total
includes taxes & fees
22 Jun - 23 Jun
Charming 1-bedroom apartment in Carmel with WiFi, 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, (7 reviews)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is SAR 647
SAR 842 total
includes taxes & fees
22 Jun - 23 Jun
Hudson Valley Farm Getaway- West/Llama Lover Lane
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 SAR 861
SAR 1,605 total
includes taxes & fees
29 Jun - 30 Jun
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is SAR 674
SAR 2,410 total
includes taxes & fees
22 Jun - 23 Jun
NEW: Chic Modern Barn Style Home in Fun Area
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, (15 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is SAR 622
SAR 802 total
includes taxes & fees
22 Jun - 23 Jun
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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 SAR 929
SAR 1,204 total
includes taxes & fees
24 Jun - 25 Jun
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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 SAR 743
SAR 1,005 total
includes taxes & fees
23 Jun - 24 Jun
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
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 SAR 1,218
SAR 1,713 total
includes taxes & fees
22 Jun - 23 Jun
Charming Cabin in Fishkill!
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is SAR 563
SAR 1,033 total
includes taxes & fees
28 Jun - 29 Jun
The Tipsy Gypsy - Studio Apartment
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

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Loved the hotel the Staff was Super Friendly and helpful we LOVED our King Suite its a great size very Spacious and plenty of room for our dogs! It would have been nice if the property outside was in better condition the grass was super dry and dead if it had been green we would have spent more time outside with the dogs. The breakfast was wonderful and had plenty of selections we would have liked to have been able to connect to our Netflix on the tv for a more enjoyable stay but it was ok with the regular channels we will probably bring our laptop next time. The bathroom was very clean ( it would have been nice if there were more places to hang towels but we made due. It would be great if the air conditioner or a fan ran in the bathroom so it didn’t get so hot but the bathtub was AWESOME!! The Staff made us feel at home every day they had Fresh Baked Cookies! We went for a dog Show in New Paltz so it was a ways away with traffic but was well worth the trip! Will definitely be coming back next year!"
Keira 4-night trip
Posted 3 hours ago
Hampton Inn & Suites Poughkeepsie

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.