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Wingdale Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Holiday Rentals in Wingdale

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

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

10.0 out of 10, Exceptional, (126)
"A delightful place. Having the lake to ourselves with magnificent views plus a property that has plenty to keep everyone active--including the very active 4 year old in our group--was amazing. Do note that the downstairs bathroom has narrow doors so mobility impaired people may not be able to access it without assistance. "
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
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, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Terrace/patio

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

10.0 out of 10, Exceptional, (194)
"Wonderful place to rest and recharge."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
The House In Highland- Secluded Retreat
Outdoor dining

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (11)
"Very nice location and private."
The House In Highland- Secluded Retreat
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (36)
"Great place for a quiet stay"
The price is HK$2,016
HK$2,588 total
includes taxes & fees
1 Nov - 2 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Interior

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (82)
"Great location and fully equipped cabin! I hope to return sometime soon Everything was perfect!"
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Chestnut on Willow Lake
Dining tables

Chestnut on Willow Lake

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is HK$3,113
HK$4,501 total
includes taxes & fees
7 Oct - 8 Oct
Chestnut on Willow Lake
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, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Dining

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (2)
"This is a property that is very good for large family gatherings, which is how we gathered for a birthday celebration. This area of CT. is great and has lots to do.The house is in the perfect location to do all of it.Again, suits large groups well. Room for everyone."
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior detail

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (3)
"Beautiful property and great location. A true retreat. "
The price is HK$6,226
HK$9,109 total
includes taxes & fees
6 Oct - 7 Oct
Whispering Estate Guest House - A Romantic Countryside Getaway
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

3.0 star property
10.0 out of 10, Exceptional, (2)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
Living area

1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

2.0 star property
9.0 out of 10, Wonderful, (8)
"Gary is a great host and provides a wonderful experience. He is the best and it was a very nice stay. Best host I have had before."
The price is HK$1,356
HK$1,588 total
includes taxes & fees
2 Oct - 3 Oct
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
Rustic Cabin in Fishkill!
Exterior

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is HK$1,774
HK$2,783 total
includes taxes & fees
1 Nov - 2 Nov
Rustic Cabin in Fishkill!
Candlewood Lake Retreat; Dock, Game Room & Firepit
Outdoor dining

Candlewood Lake Retreat; Dock, Game Room & Firepit

10.0 out of 10, Exceptional, (47)
"Everything was great! Thank you!"
The price is HK$6,724
HK$12,211 total
includes taxes & fees
3 Oct - 4 Oct
Candlewood Lake Retreat; Dock, Game Room & Firepit
Be in Nature at this Gorgeous Riverfront Cabin
Smart TV, books

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (21)
"An ideal retreat. The modern cabin offered serene surroundings with stunning views of the woods and creek. The property was well-maintained, and the property manager was highly responsive. A perfect choice for a peaceful and refreshing getaway."
Be in Nature at this Gorgeous Riverfront Cabin
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (82)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Exterior

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

9.8 out of 10, Exceptional, (10)
"We had a lovely weekend stay at this stone house with our family. There were a lot of lovely artistic touches throughout the house and it was obvious it was well cared for. The hosts have gone above and beyond making sure we had everything we needed. Kitchens and bathrooms were well stocked and lots of lovely "welcome" items in all the rooms. Would definitely recommend staying here again."
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (40)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
The Goshen Glass Chalet
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford
TV, fireplace

Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford

10.0 out of 10, Exceptional, (5)
"We were in town for a family wedding and found this quaint little apartment that was quiet and secluded. Being on the river we did find a lot of bugs, but nothing we couldnt handle. The owners were extremely nice and responsive and we had a wonderful stay. "
The price is HK$2,033
HK$2,784 total
includes taxes & fees
9 Oct - 10 Oct
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford
Cabin in the heart of the Hudson Valley, Cabin 2
Property grounds

Cabin in the heart of the Hudson Valley, Cabin 2

9.6 out of 10, Exceptional, (25)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
The price is HK$848
HK$1,370 total
includes taxes & fees
7 Oct - 8 Oct
Cabin in the heart of the Hudson Valley, Cabin 2
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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Top Wingdale Hotel Reviews

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

10/10 Excellent
"Clean room, good breakfast and friendly staff"
Aleida 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Find out more about Wingdale

Find out more about Wingdale

Search for holiday rentals in Wingdale on Expedia! You can easily find your home rentals, villas, holiday apartments in Wingdale using one of the methods below:

  • View our selection of featured holiday rentals in Wingdale
  • Use the map to find apartments and other holiday homes in the Wingdale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wingdale while they last

Look no further and take a look at our great range of rental properties in Wingdale!

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?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This holiday home rental outside of Wingdale is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

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. While here, Dover Veterans Memorial Library and Harlem Valley Golf Club are other places worth a visit.

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.