Photo by Anna Arsenault

Wingdale Holiday Rentals

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Check prices for these dates

Tonight
18 Feb - 19 Feb
Tomorrow
19 Feb - 20 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

Holiday Rentals in Wingdale

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Outdoor dining

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (120)
"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Spacious New Luxurious holiday house in lovely Hudson Valley
Terrace/patio

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
The price is AU$1,299
includes taxes & fees
1 Mar - 2 Mar
Spacious New Luxurious holiday house in lovely Hudson Valley
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
On the beach, sun-loungers

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (83)
"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
Hidden Charm in Hudson Valley In Dutchess County
Smart TV, fireplace, table football, ping pong

Hidden Charm in Hudson Valley In Dutchess County

2.0 star property
10.0 out of 10, Exceptional, (13)
"thank you to the host, she was responsive, the home was amazing, clean, secluded, perfect size for our family and the property was beautiful. we loved having 2 beds on the main floor, as my mom is elderly, so no stairs was incredibly convenient. house had all the supplies we needed to cook/clean, so it was just terrific!! Thank you!"
Hidden Charm in Hudson Valley In Dutchess County
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!
Smart TV

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (5)
"This place is amazing!! The house had everything we needed and more. We really enjoyed our stay and also be able to host some of our family in the area was precious. My daughters rented equipment for the babies which worked out well. The house is very spacious and 5 adults and 3 children fit nicely. Very highly recommend. The pier was fun to hang out on but due to weather we were to enjoy the lake as much. Easy to find, and owners were very responsive. "
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

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

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is AU$461
includes taxes & fees
19 Feb - 20 Feb
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Outdoor dining

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.4 out of 10, Exceptional, (9)
"We stayed here for work event and the location was perfect. Not too close, not too far away. Its snowed one evening but the driveway was not slippery at all. The house was very clean and kept in order. Plenty of room in the bedrooms and bathroom. The operational fireplace was also an added bonus. "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Outdoor dining

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (22)
"Mariana is a wonderful host. She communicates well and is very efficient in responding to any questions or inquiries you may have.The cabin is very clean, and has just about everything you would need. We really enjoyed using the fireplace! 10/10 recommend. "
Cozy & Chic Cabin by the Lake, with access to private Beach!
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Outdoor spa tub

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (106)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Litchfield Hills Hideaway
Fridge, microwave, oven, stovetop

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (55)
"Great place to end our Gilmore Girls adventure!!! The Hideaway was clean and cozy, and the hosts are very professional! We would stay here again!!!!"
The price is AU$410
includes taxes & fees
23 Feb - 24 Feb
Litchfield Hills Hideaway
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (75)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Hudson Valley Horse Farm Retreat in Salt Point
Miscellaneous

Hudson Valley Horse Farm Retreat in Salt Point

10.0 out of 10, Exceptional, (55)
"Nice house, great location, helpful host."
Hudson Valley Horse Farm Retreat in Salt Point
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Property grounds

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

10.0 out of 10, Exceptional, (16)
"My time spent at the lake house with my family was unforgettable. Nestled along the serene shoreline, the house offered stunning lake views from every window. Mornings began with coffee on the spacious deck, watching the sun rise over the water. Days were filled with family fun. The house itself was cozy yet modern, with plush furnishings, a crackling fireplace, and a fully-equipped kitchen where we cooked meals together. Evenings were spent playing board games, hanging out by the fire pit. It...
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Lakefront Winter Winderland in New England Just 2 Hours From NYC
Interior

Lakefront Winter Winderland in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (65)
"We had a beautiful, peaceful, cozy fall weekend at this cabin. The location is stunning next to the lake and across the street from hiking trails. The cabin had everything we needed and was quite comfortable. The only caveat is that it abuts a road with aggressive drivers so I did not feel comfortablet letting my dog off leash. Other than that, ideal. I will definitely be back! "
Lakefront Winter Winderland in New England Just 2 Hours From NYC
New One Bedroom Apartment Centrally Located in Southbury
Exterior

New One Bedroom Apartment Centrally Located in Southbury

10.0 out of 10, Exceptional, (1)
The price is AU$179
includes taxes & fees
19 Feb - 20 Feb
New One Bedroom Apartment Centrally Located in Southbury
Escape to a Celebrity Chef's Waterfront Lake House
Interior

Escape to a Celebrity Chef's Waterfront Lake House

10.0 out of 10, Exceptional, (1)
Escape to a Celebrity Chef's Waterfront Lake House
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Interior

Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!

10.0 out of 10, Exceptional, (11)
"This was just what we were looking for. The house was roomy, open and charming. It was also relaxing to sit on the back deck surrounded by trees and listening to the calming sound of the brook. It felt like you out in the countryside yet the cute village of Sandy Hook along with Newtown restaurants and shopping were less than 10 minutes away."
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
The Long View of Candlewood Lake
Smart TV, fireplace

The Long View of Candlewood Lake

10.0 out of 10, Exceptional, (20)
"A great place to stay with the family! "
The Long View of Candlewood Lake
Two Bedroom Cottage Close To Town
Fridge, microwave, oven, stovetop

Two Bedroom Cottage Close To Town

9.4 out of 10, Exceptional, (19)
"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "
Two Bedroom Cottage Close To Town
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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Other types of properties in Wingdale you may be interested in

Ethan Allen Hotel
Seasonal outdoor pool

Ethan Allen Hotel

3.5 star property
7.8 out of 10, Good, (1002)
"Great place !"
The price is AU$172
includes taxes & fees
24 Feb - 25 Feb
Ethan Allen Hotel
Hotel Zero Degrees Danbury
Lobby lounge

Hotel Zero Degrees Danbury

4.0 star property
9.0 out of 10, Wonderful, (1004)
"This was a beautiful hotel. The staff was amazing and attentive. Only issue I had was that I called a month before my stay because this site says microwave upon request and was told the room I booked had one to find out when I got there it wasn’t and I couldn’t get one. Plus the water on the shower didn’t get hot. "
The price is AU$286
includes taxes & fees
27 Feb - 28 Feb
Hotel Zero Degrees Danbury
HYATT house Fishkill/Poughkeepsie
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

HYATT house Fishkill/Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (999)
"We had a family 1 night stay. Bed was comfy, multiple tvs is the 2 bedroom. Only negative was too much chlorine in the pool and a bit cold. "
The price is AU$176
includes taxes & fees
25 Feb - 26 Feb
HYATT house Fishkill/Poughkeepsie
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.

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?

Escape to a Celebrity Chef's Waterfront Lake House: This holiday home rental outside of Wingdale is located near skiing, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Lake Waramaug State Park. 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.