Photo by Anna Arsenault

Wingdale Holiday Rentals

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Holiday Rentals in Wingdale

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, (14)
"This house does have a lovely view that allowed us to take in the changing leaves off the reflection of the lake. The house is smaller than it appears in the photos and not quite as comfortable to just hang out, at least inside.The couch fits three, but there aren't other chairs in the living area. There are great little outside areas though. Communication with Katherine was great. Previous tenants had broken the washer which was a drag and due to weather (drought conditions) we couldn't use...
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun-loungers
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (73)
"Our group of 2 couples enjoyed our week in the Hudson Valley area. We all commented on the excellent beds and pillows, the view of the lake from the house and the quiet of the neighborhood. Would stay here again."
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Beach nearby, beach towels
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior detail
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.2 out of 10, Wonderful, (35)
"I loved the location surrounded by mostly woods and the quiet atmosphere. The hosts are very nice and were very helpful. Everything I needed was inside. I may be back!"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Miscellaneous
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
10.0 out of 10, Exceptional, (11)
"This property was even more beautiful than it appeared in the photos. The wooded backyard was also spacious and lovely. We were so happy with the view of the lake and how peaceful the space was. The owners are easy to communicate with and prompt to respond. We will absolutely be going back. "
The price is AU$1,270
includes taxes & fees
18 Nov - 19 Nov
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Exterior
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (80)
"Amazing location on a completely private small lake just a few minutes off the Taconic Parkway. Host is very helpful, and very artistic. Sleeping on a pull out couch was initially off-putting, but it is very high quality and fairly comfortable, and works for the space. So many birds to see and hear! Nice hiking trails on the large property, which has adjacent preserved land. "
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Cabin in the heart of the Hudson Valley, Cabin 4
Outdoor dining
Cabin in the heart of the Hudson Valley, Cabin 4
8.8 out of 10, Excellent, (17)
"The description of the property was accurate; however, a few things surprised me that would have affected my decision to book or not. First, the house is located beside a busy road where traffic is moving all hours of the day and night at 35-55 mph. For some, this isn't a big deal. For others, it's not as quiet as described. Thankfully, I was delighted to see the room provided a noise machine. Secondly, there is no fan. Only the A/C and heater provided any air movement if you didn't want the...
The price is AU$253
includes taxes & fees
17 Nov - 18 Nov
Cabin in the heart of the Hudson Valley, Cabin 4
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, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Outdoor dining
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.8 out of 10, Exceptional, (25)
"Amazing location, right along the lake. The house was so organized and clean. Very impressed! "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, fireplace, ping pong, stereo
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
9.8 out of 10, Exceptional, (19)
"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
The Long View of Candlewood Lake
Smart TV, fireplace
The Long View of Candlewood Lake
10.0 out of 10, Exceptional, (17)
"The house faces the lake and offers tranquil and beautiful views from most rooms. It was meticulously maintained and very attractive and comfortable. It was stocked with everything you would need to be comfortable and to feel like home. We stayed 2 nights and thoroughly enjoyed it!"
The Long View of Candlewood Lake
Idillic summer getaway in Litchfield Hills, CT.
Exterior
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Miscellaneous
Stay 3 Nights or Longer Until January 31 and Get 15% Off
9.8 out of 10, Exceptional, (28)
"Property and home are beautiful. The larger home on adjacent property (Sunny Day) is close and if a larger group is staying there can be loud in the tranquil setting during the day. Otherwise, the setting is beautiful and the house was perfect for our family of 6 (3 couples). We enjoyed the kayak, paddle board, fishing, evening fire pit and views from upstairs deck and downstairs patio. "
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Candlewood Lake Retreat with year round views
Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (31)
"This is a very nice home with a well equipped kitchen. The living room and dining areas are spacious. We could have used more closet space but it wasn’t that much of an issue. The driveway could use grading but had ample parking."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Exterior
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
10.0 out of 10, Exceptional, (78)
"Very large house just like the photos. Host is present and responsive. We had the entire property to ourselves. Nice yard for some whiffle ball and outdoor activities. Swimming is possible at the public lake access which is about a mile away or so. Overall, a very nice stay at a very nice property. We were 10 adults (friends weekend) and fit just fine. "
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
The Scenic Mansion With Breathtaking View
Fridge, microwave, oven, stovetop
The Scenic Mansion With Breathtaking View
9.6 out of 10, Exceptional, (11)
"So nice we keep coming back. Can't recommend highly enough and will be back in the spring. "
The Scenic Mansion With Breathtaking View
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Outdoor dining
Lakefront New York Abode w/ Deck, Grill & Fire Pit
9.2 out of 10, Wonderful, (9)
"My multigenerational family enjoyed canoeing, kayaking, ping pong, billiards, pop a shot, and the fire pit. Steep stairs to the upstairs shower make it tough for anyone with mobility issues . Very quiet location yet near to shopping and trains to NYC. "
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Pet-Friendly Beacon Area Vacation Rental: 6 Acres
Fridge, microwave, dishwasher, toaster
Pet-Friendly Beacon Area Vacation Rental: 6 Acres
10.0 out of 10, Exceptional, (10)
"Property worked very well for us. Pool was great. (Couple of notes: The stay listed above is slightly incorrect. We arrived on Wed Jun 26 and left on Sun June 30). We requested additional chairs for the pool area from the owner but they were never delivered."
Pet-Friendly Beacon Area Vacation Rental: 6 Acres
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, (1001)
"If you need a place in Danbury or the surrounding area, this hotel is very near the Mall and is clean and well managed. "
The price is AU$183
includes taxes & fees
21 Nov - 22 Nov
Ethan Allen Hotel
Quality Inn Poughkeepsie
Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building
Quality Inn Poughkeepsie
2.5 star property
8.0 out of 10, Very good, (304)
"nothing to say"
The price is AU$151
includes taxes & fees
28 Nov - 29 Nov
Quality Inn Poughkeepsie
Best Western Fishkill Inn & Suites
Suite, 2 Queen Beds, Non Smoking, Kitchen (Shower Only;with Sofabed)
Best Western Fishkill Inn & Suites
3.5 star property
8.6 out of 10, Excellent, (663)
"The room was clean and spacious. The service provided was nice. There were two electric charging stations near the office. I love how each unit had privacy"
The price is AU$159
includes taxes & fees
8 Dec - 9 Dec
Best Western Fishkill Inn & Suites
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?

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock: This holiday home rental outside of Wingdale is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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. In the wider area, you’ll find Thunder Ridge Ski Resort and Stormville Airport Antique Show & Flea Market.

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.