Photo by Anna Arsenault

Wingdale holiday homes

We found 203 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Wingdale to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Wingdale

Showing deals for:6 Nov - 13 Nov

view from the kitchen window
kitchen island w/reclaimed wood
Entry foyer
Our home sweet home!
Exceptional
(26 reviews)

TREEMENDOUS VIEWS COTTAGE

Amenia

8% off
NZ$6,812
for 7 nights, 1 home
NZ$973 per night
includes taxes & fees
TREEMENDOUS VIEWS COTTAGE
Garden Level Den/ Ping Pong, piano, board games and TV
Great room view from the second floor
Beautiful country kitchen with all modern appliances
The Barn
Exceptional
(41 reviews)

Modern Barn, NEW Luxurious Home

New Preston

8% off
NZ$12,380
for 7 nights, 1 home
NZ$1,769 per night
includes taxes & fees
Modern Barn, NEW Luxurious Home
Property grounds
Outdoor dining
Living area
Interior
Exceptional
(20 reviews)

Beautiful lake view home on Whaley Lake in Holmes, NY.

Holmes

8% off
NZ$8,299
for 7 nights, 1 home
NZ$1,186 per night
includes taxes & fees
Beautiful lake view home on Whaley Lake in Holmes, NY.
Seating area in kitchen close to the screened in porch
Property grounds
Guests love spending quality time together in the living room
Lovely outdoor area and screened in porch to enjoy nature (without the bugs!)
Exceptional
(84 reviews)

Historic Warren/Kent Home

Cornwall Bridge

7% off
NZ$4,521
for 7 nights, 1 home
NZ$646 per night
includes taxes & fees
Historic Warren/Kent Home
Interior
Property grounds
Dining
Property grounds
Exceptional
(7 reviews)

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

Holmes

8% off
NZ$4,906
for 7 nights, 1 home
NZ$701 per night
includes taxes & fees
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Exterior
Christmas vibes!!
Interior
Dinning and sitting room - get ready for the sunsets.
Wonderful
(10 reviews)

Hidden Gem on Private Road - Hike; Swim, Ski, Sauna; Relax - Repeat!!

Sherman

12% off
NZ$4,713
for 7 nights, 1 home
NZ$673 per night
includes taxes & fees
Hidden Gem on Private Road - Hike; Swim, Ski, Sauna; Relax - Repeat!!
Private kitchen
Exterior detail
Pool
Property grounds
Exceptional
(38 reviews)

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

New Fairfield

8% off
NZ$4,238
for 7 nights, 1 apartment
NZ$605 per night
includes taxes & fees
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Interior
Open floor plan is great for groups
Front entrance is a sun room in the winter and porch in the summer.
Do you enjoy cooking/baking? High-end kitchen with everything you need.
Exceptional
(6 reviews)

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Millbrook

8% off
NZ$6,248
for 7 nights, 1 home
NZ$893 per night
includes taxes & fees
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Wingdale getaway

Learn about the unique charm of Wingdale with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Wingdale

Are you hoping to discover top things to see and do in the area? Venture out of your holiday home and check out everything that makes Wingdale a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Thunder Ridge Ski Resort (9.6 mi / 15.5 km)
  • Beekman Golf Course (11.4 mi / 18.3 km)
  • Hopkins Vineyard (11.7 mi / 18.9 km)
  • Millbrook Vineyards and Winery (14.7 mi / 23.7 km)
  • Mohawk Mountain Ski Area (18.6 mi / 30 km)
  • SplashDown Beach (18.7 mi / 30.2 km)

Exploring the natural features in Wingdale

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Wingdale is a great place to spend some time outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Lake Waramaug State Park (10.4 mi / 16.8 km)
  • Lake Waramaug (11.3 mi / 18.2 km)
  • Kent Falls State Park (11.8 mi / 19 km)
  • Candlewood Lake (12.1 mi / 19.6 km)
  • Steep Rock Preserve (12.6 mi / 20.4 km)
  • Lake Lillinonah (16.2 mi / 26.1 km)

How to get to and around Wingdale

Fly into Danbury, CT (DXR-Danbury Municipal), the closest airport, located 19.4 mi (31.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Oxford, CT (OXC-Waterbury - Oxford), which is 25 mi (40.3 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Wingdale?
The most sought-after types of holiday homes in Wingdale are cabins. Looking for something different? Bookabach has a variety of options to match our guests' unique requirements, so you'll see properties in all shapes and sizes. The ideal fit is ready and waiting for you — grab yours today.
How much does it cost to rent a holiday home in Wingdale?
Property type, season and length of stay are some things that can influence the price of a holiday home. Simply click on your travel dates to find your ideal escape. From quaint country cottages to expansive villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Wingdale?
The average price for a holiday home close to the beach in Wingdale will depend on when you're going and the type and size of property you're looking for. You can find prices quickly and easily on Bookabach by entering your destination and preferred travel dates. Then use the handy filters to pick the number of bedrooms and amenities important to you, like air conditioning, WiFi and a pool.
Are there pet-friendly holiday homes in Wingdale?
Pack a suitcase and a bone for your pooch because Wingdale has four holiday homes that put out the welcome mat to pets. Let your furriest pal enjoy the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your destination and dates, then check the "Pets allowed" filter box.
What are popular home amenities in Wingdale?
When it comes to home amenities that people are searching for in Wingdale, a beach view, a firepit and a garden are at the top of the list. With Bookabach holiday homes, there are options to fit your taste and style, whether you're holidaying with your partner, your friends or even pets.
Are there large group holiday homes in Wingdale?
Yes, you can pick from one of two holiday homes in Wingdale that can host a group of five or more guests. From family trips to special occasions, these stays have ample space to spend time with the people you love.
Are there holiday homes in Wingdale that welcome kids?
Gather the whole crew for the adventure of a lifetime in Wingdale at one of our four family-friendly holiday homes. Lots of these stays come with conveniences that are perfect for trips with children, including kitchens, extra bedrooms and patios. Just click on the "Properties good for families" filter box and select your favourite.
Are there holiday homes with WiFi in Wingdale?
Wingdale has four holiday homes with WiFi, so you can stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to writing and sending emails, these Bookabach homes will keep you online.
How can I find holiday homes with air conditioning in Wingdale?
Wingdale has three holiday homes where you'll be able to unwind in air-conditioned comfort. To book a property on Bookabach that has this amenity, enter your desired travel dates and use the filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Wingdale?
The minimum required age is generally 16, 18 or 21. It can vary between properties on Bookabach, so check the rules of your preferred Wingdale stay before booking your escape.
How long can I rent a holiday home in Wingdale for?
The amount of time you can stay in a Wingdale holiday home for depends on each property. Simply tap in your travel dates to see available options that offer extended stays. They include the things you need to make your extended holiday more comfortable and convenient, like kitchens and yards. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.