Photo by Anna Arsenault

Wingdale holiday rentals

We found 210 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:25 Sept - 2 Oct

Image gallery for GREAT ESCAPE FROM THE CITY, WITHIN 15 MINUTES OF MANY WEDDING VENUES. INQUIRE!

A beautiful sunrise at the peaceful cabin
10 out of 10, Exceptional, (61 reviews)
Exceptional
(61 reviews)

GREAT ESCAPE FROM THE CITY, WITHIN 15 MINUTES OF MANY WEDDING VENUES. INQUIRE!

Dover Plains

28% off
Price is AU$10,694
for 7 nights, 1 cabin
AU$1,528 per night
includes taxes & fees
GREAT ESCAPE FROM THE CITY, WITHIN 15 MINUTES OF MANY WEDDING VENUES. INQUIRE!

Find spaces that suit your style

  • 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)
  • Millbrook Vineyards and Winery (14.7 mi / 23.7 km)
  • Richter Park Golf Course (16.2 mi / 26.1 km)
  • Mohawk Mountain Ski Area (18.6 mi / 30 km)
  • SplashDown Beach (18.7 mi / 30.2 km)
  • Beekman Golf Course (11.4 mi / 18.3 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:

  • Tymor Park (7 mi / 11.2 km)
  • Lake Waramaug State Park (10.4 mi / 16.8 km)
  • Lake Dutchess (10.5 mi / 16.9 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)

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? Stayz 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 Stayz 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 Stayz 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 Stayz. 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 Stayz 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 Stayz 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 Stayz 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 Stayz, 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.