Photo by Anna Arsenault

Wingdale holiday rentals

We found 206 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:27 Nov - 4 Dec

Room
Outdoor dining
Living area
Interior
Exceptional
(21 reviews)

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

Holmes

8% off
AU$6,743
for 7 nights, 1 home
AU$963 per night
includes taxes & fees
Beautiful lake view home on Whaley Lake in Holmes, NY.
view from the kitchen window
kitchen island w/reclaimed wood
Our home sweet home!
Swing on our porch!
Exceptional
(26 reviews)

TREEMENDOUS VIEWS COTTAGE

Amenia

8% off
AU$5,509
for 7 nights, 1 home
AU$787 per night
includes taxes & fees
TREEMENDOUS VIEWS COTTAGE
Seating area in kitchen close to the screened in porch
Property grounds
Lovely outdoor area and screened in porch to enjoy nature (without the bugs!)
Stone fireplace is the centerpiece of the home and a great place to take photos
Exceptional
(84 reviews)

Historic Warren/Kent Home

Cornwall Bridge

8% off
AU$3,636
for 7 nights, 1 home
AU$519 per night
includes taxes & fees
Historic Warren/Kent Home
Private kitchen
Property grounds
Dining
Interior
Exceptional
(7 reviews)

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

Holmes

8% off
AU$3,936
for 7 nights, 1 home
AU$562 per night
includes taxes & fees
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Dining
Christmas vibes!!
Interior
Exterior
Wonderful
(11 reviews)

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

Sherman

11% off
AU$3,876
for 7 nights, 1 home
AU$554 per night
includes taxes & fees
Hidden Gem on Private Road - Hike; Swim, Ski, Sauna; Relax - Repeat!!
Front entrance is a sun room in the winter and porch in the summer.
Open floor plan is great for groups
Do you enjoy cooking/baking? High-end kitchen with everything you need.
Plenty of space for outdoor dining and hanging out
Exceptional
(6 reviews)

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Millbrook

8% off
AU$5,048
for 7 nights, 1 home
AU$721 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:

  • Whaley Lake (7.8 mi / 12.6 km)
  • 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)

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 best area to stay in Wingdale when booking a holiday rental?
When considering a holiday rental in Wingdale, New York, one of the most appealing areas to stay is near the charming neighbourhoods that surround the town. Wingdale itself offers a tranquil atmosphere, ideal for those looking to escape the hustle and bustle of city life. The area is characterised by its scenic landscapes and proximity to nature, making it a great choice for outdoor enthusiasts.A highlight of staying in Wingdale is its close vicinity to the beautiful Appalachian Trail, which offers stunning hiking opportunities and breathtaking views. Additionally, the nearby Harlem Valley Rail Trail is superb for cycling and leisurely walks, providing a delightful way to explore the natural beauty of the region.In terms of holiday rentals, Wingdale has a variety of properties that cater to different preferences, from cosy cottages to spacious homes, allowing visitors to choose what best suits their needs.
Where are the best Wingdale ski resort rentals?
For skiing near Wingdale, the closest options are found at the nearby Catamount Ski Area or the larger resorts in the Berkshires. In Wingdale itself, travellers can find a variety of cozy cabins and cottages that cater to winter sports enthusiasts. Many of these properties offer essential amenities such as fully equipped kitchens, wood-burning stoves or fireplaces, and comfortable living areas, superb for relaxing after a day on the slopes.In the surrounding areas, particularly in nearby towns like Dover Plains and Pawling, visitors can discover more extensive rental options, including rustic lodges and modern homes. These often come with additional features like hot tubs, outdoor decks, and proximity to local dining options, enhancing the overall experience.For those looking to explore beyond skiing, the region presents ample opportunities for hiking and enjoying scenic winter landscapes. Rentals in these areas typically offer a serene escape, equipped with necessary comforts such as heating, Wi-Fi, and sometimes even game rooms for family entertainment.
What is the most popular type of holiday rental accomodation in Wingdale?
In Wingdale, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically feature spacious interiors with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them suitable for families or larger groups. Many holiday houses also boast outdoor spaces such as gardens or decks, superb for enjoying the picturesque surroundings.
Are there any family house rentals in Wingdale?
In Wingdale, New York, there are several family-friendly house rentals available, making it a great spot for group getaways. Visitors can find homes located in scenic surroundings, often featuring spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely. Many properties also include amenities such as Wi-Fi and laundry facilities for added convenience.The area is well-positioned for exploring the natural beauty of the Hudson Valley, with nearby attractions like the Appalachian Trail for hiking enthusiasts and local parks that provide recreational activities.
Are there pet-friendly house rentals in Wingdale?
In Wingdale, there are several pet-friendly house rentals available, making it a great destination for travellers looking to bring their furry companions along. Many of these holiday rentals offer spacious rooms, often featuring amenities such as fully equipped kitchens, outdoor spaces, and comfortable living areas. The scenic surroundings allow for enjoyable walks and outdoor activities with pets.Additionally, the area benefits from its proximity to local parks and nature reserves, providing ample opportunities for hiking and exploring the beautiful landscapes of the Hudson Valley.
Are there any remote work holiday rentals in Wingdale?
In Wingdale, New York, there are several holiday rentals that cater to remote workers, making it an excellent choice for those looking to combine work and leisure. Many of these properties offer essential amenities such as free Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas conducive to productivity.The area itself is located in a picturesque setting, providing a tranquil environment for remote work while still being close to nature. Visitors can enjoy nearby attractions like the Harlem Valley Rail Trail, superb for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Wingdale?
In Wingdale, popular rental amenities include features that enhance comfort and convenience for travellers. Many properties offer a kitchen, allowing guests to prepare their own meals, alongside a blender for smoothies or other culinary needs. Outdoor living is also emphasised, with balconies and porches or lanais providing spaces to relax and enjoy the surrounding scenery. Additionally, a number of rentals are pet-friendly, making it easier for guests to bring their furry companions along on their stay.
When is the best time to visit Wingdale for a holiday rental?
The best time to visit Wingdale for a holiday rental is during the peak season from February to April. This period attracts nature enthusiasts and those seeking outdoor adventures, as the region comes alive with opportunities for hiking, birdwatching, and exploring the tranquil landscapes of the Hudson Valley.February, in particular, offers a unique charm with mild temperatures ranging from 0 to low 10s Celsius, making it an ideal time for outdoor activities. Visitors can enjoy the picturesque views and engage in local events, all while soaking in the serene environment that Wingdale has to offer.For travellers looking for a more budget-friendly option, November is a wonderful time to visit. During this month, you can experience the stunning autumn foliage, which paints the area in vibrant hues of orange and gold. It's a quieter time, great for those who appreciate a peaceful retreat while still enjoying the beauty of nature.
What are the top attractions in Wingdale?
In Wingdale, New York, visitors can enjoy a range of attractions that highlight the area's natural beauty and recreational opportunities. The nearby Harlem Valley Rail Trail offers scenic walking and biking paths, superb for those looking to explore the great outdoors. Additionally, the charming Lake Dutchess provides a tranquil setting for fishing, kayaking, or simply relaxing by the water.For those interested in local history, the East Fishkill Historical Society offers insights into the region's past, while the nearby town of Dover Plains features quaint shops and delightful eateries that reflect the local culture. Nature enthusiasts may also appreciate the proximity to the Appalachian Trail, which is accessible for hiking and offers stunning views of the surrounding landscapes.
Are all fees included in the Wingdale holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Wingdale holiday homes with parking?
Stayz offers a wide selection of holiday homes in Wingdale with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Wingdale holiday homes?
You can find great discounts on holiday homes in Wingdale on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Wingdale holiday home booking on Stayz?
To find Wingdale holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Wingdale?
A long-stay holiday home in Wingdale is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Wingdale holiday home?
Book your Wingdale holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Wingdale?
Prices for holiday homes in Wingdale vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Wingdale to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.