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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Wingdale vacation rentals

Private kitchen

1. Gorgeous 4-bedroom house on lovely Candlewood Lake perfect for families

Gorgeous 4-bedroom house on lovely Candlewood Lake perfect for families
Brookfield
The price is AED 1,983
AED 3,515 total
includes taxes & fees
8 Sep - 9 Sep
Gorgeous 4-bedroom house on lovely Candlewood Lake perfect for families
Miscellaneous

2. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AED 1,653
AED 2,547 total
includes taxes & fees
30 Aug - 31 Aug
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Private kitchen

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
The price is AED 250
AED 530 total
includes taxes & fees
1 Sep - 2 Sep
Cozy private room in a shared home with a Full-size bed and private bathroom.
Property grounds

4. 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 AED 404
AED 760 total
includes taxes & fees
7 Sep - 8 Sep
Hoppy Hill Farm House
Smart TV, fireplace, books

5. 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, (23 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 AED 716
AED 923 total
includes taxes & fees
1 Sep - 2 Sep
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Exterior

6. 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
9.6 out of 10, Exceptional, (5 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is AED 1,175
AED 1,828 total
includes taxes & fees
26 Aug - 27 Aug
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
TV, fireplace

7. 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, (19 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AED 893
AED 1,652 total
includes taxes & fees
8 Sep - 9 Sep
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Interior

8. 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, (6 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.
The price is AED 1,469
AED 3,087 total
includes taxes & fees
30 Aug - 31 Aug
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Cookware/dishes/utensils

9. Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"Nicole is a wonderful host. We had a fantastic stay at her house. The home was beautifully prepared, and we felt very comfortable throughout our visit. Even though it was a rainy weekend, we were still able to enjoy the huge hot tub and had a great time playing the card games and board games provided. Thank you!!"
United States
W Y.
The price is AED 1,653
AED 2,850 total
includes taxes & fees
20 Sep - 21 Sep
Awesome Lake Home with tons of fun!
Property grounds

10. 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.
The price is AED 294
AED 491 total
includes taxes & fees
31 Aug - 1 Sep
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Coffee/tea maker, fridge, microwave, oven

11. "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 AED 754
AED 2,161 total
includes taxes & fees
8 Sep - 9 Sep
"Country outside the city " 3 bedrooms 2 full bathrooms
1 bedroom, internet, bed sheets

12. 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 AED 367
AED 681 total
includes taxes & fees
5 Sep - 6 Sep
Welcome to Sweet Abby Rose!
Exterior

13. 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 AED 1,111
AED 1,690 total
includes taxes & fees
31 Aug - 1 Sep
Rustic Cabin in Fishkill!
Outdoor dining

14. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (58 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
The price is AED 3,580
AED 6,290 total
includes taxes & fees
17 Sep - 18 Sep
Candlewood Lake Retreat with Private Dock
Exterior

15. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is AED 1,818
AED 2,614 total
includes taxes & fees
26 Aug - 27 Aug
Chestnut on Willow Lake
1 bedroom, iron/ironing board, WiFi (free), bed sheets

16. 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 AED 621
AED 1,033 total
includes taxes & fees
20 Sep - 21 Sep
Cabin in the Heart of the Hudson Valley, Cabin 1
Outdoor dining

17. 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, (74 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is AED 960
AED 1,271 total
includes taxes & fees
31 Aug - 1 Sep
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Terrace/patio

18. 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 AED 621
AED 1,037 total
includes taxes & fees
30 Aug - 31 Aug
Cabin in the heart of the Hudson Valley, Cabin 3
Property grounds

19. Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Danbury
9.0 out of 10, Wonderful, (2 reviews)
"Very nice hosts and immaculately clean property. Hot tub was great. My only mention is that there isn’t actually any lake access which was misleading. We did use the hosts’ kayaks and put them on our cars to go boating which was free, but swimming is not free and about a 10 min drive away. The hosts also live above the suite (not mentioned) but we had a private entrance."
United States
Kaitlyn C.
The price is AED 1,223
AED 2,057 total
includes taxes & fees
8 Sep - 9 Sep
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Interior

20. 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, (15 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AED 790
AED 1,022 total
includes taxes & fees
26 Aug - 27 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent
"Convenient location, breakfast a plus, clean rooms. Unfortunately the WiFi was not working, but it was being fixed while we were there"
Richard 1-night trip
Posted less than an hour ago
SureStay Plus Hotel by Best Western Highland 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Wingdale offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and an electric kettle, 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.