Wingdale holiday homes, NY, USA: holiday houses & more

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:18 Jul - 25 Jul

Exceptional

(42 reviews)

Waterfront Family Retreat on Candlewood Lake

New Milford, CT

8% off

NZ$2,851 per night

includes taxes & fees

Exceptional

(6 reviews)

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

Holmes, NY

8% off

NZ$690 per night

includes taxes & fees

Fair Rising: our beautiful country estate!

Exceptional

(22 reviews)

An acclaimed photographers country estate, arts community, near private schools!

Sharon, CT

16% off

NZ$1,044 per night

includes taxes & fees

Exceptional

(52 reviews)

Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Cornwall Bridge, CT

8% off

NZ$1,324 per night

includes taxes & fees

Exceptional

(65 reviews)

The Lucky Goat, a quiet country cottage about an hour from NYC, just off the TSP

Pleasant Valley, NY

12% off

NZ$417 per night

includes taxes & fees

Wonderful

(36 reviews)

Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

Pleasant Valley, NY

8% off

NZ$280 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Wingdale

View of The Lake House and Lake Weil from game room

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

Sleeps 14 · 5 bedrooms · 3 bathrooms

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)
Millbrook Vineyards and Winery (14.7 mi / 23.7 km)
Centennial Golf Club (15.6 mi / 25.1 km)
Mohawk Mountain Ski Area (18.6 mi / 29.9 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)
Innisfree Garden (12.4 mi / 19.9 km)
Steep Rock Preserve (12.6 mi / 20.4 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.