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Wingdale Vacation Rentals

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Vacation Rentals in Wingdale

Our top choices for Wingdale vacation rentals

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

10.0 out of 10, Exceptional, (124)
"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!

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (28)
"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

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

9.8 out of 10, Exceptional, (29)
"Great place for a quiet stay"
The price is CA $356
CA $456 total
includes taxes & fees
Sep 21 - Sep 22
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

2.0 star property
9.6 out of 10, Exceptional, (7)
"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 CA $240
CA $281 total
includes taxes & fees
Sep 1 - Sep 2
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.0 out of 10, Wonderful, (21)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

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

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Cabin in the heart of the Hudson Valley, Cabin 4

9.2 out of 10, Wonderful, (25)
"Exactly as advertised "
The price is CA $150
CA $242 total
includes taxes & fees
Sep 3 - Sep 4
Cabin in the heart of the Hudson Valley, Cabin 4

Lake Oasis with Firepit, Game room and Kayaks

8.8 out of 10, Excellent, (3)
"Our weekend at Rory’s home was everything and then some. The hospitality was truly unmatched. Rory bought us a new grill, provided pizza, and gave us fantastic suggestions to go do in the area. There was so much to do around the house between using the kayaks during the day and ending the night by the bonfire. I highly recommend staying here for a weekend getaway, reunion, or even to just unwind and get away from the city. 10/10 experience, would absolutely stay here again! "
Lake Oasis with Firepit, Game room and Kayaks

Cabin in the heart of the Hudson Valley, Cabin 2

9.6 out of 10, Exceptional, (22)
"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 CA $150
CA $242 total
includes taxes & fees
Sep 1 - Sep 2
Cabin in the heart of the Hudson Valley, Cabin 2

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is CA $378
CA $577 total
includes taxes & fees
Sep 2 - Sep 3
Rustic Cabin in Fishkill!

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (45)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

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

9.4 out of 10, Exceptional, (81)
"Wonderful lake retreat 🥾"
Summer Lake Cottage, private beach, Berkshire Hills, small village

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

10.0 out of 10, Exceptional, (4)
"This ground level apartment is comfortable and exceptionally clean, and above all its location in a bucolic setting made our two night stay peaceful and restful. Knowing location of the key made the check-in very easy, and the kitchen facilities met our needs. "
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford

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.

Cabin in the Heart of the Hudson Valley, Cabin 1

9.8 out of 10, Exceptional, (28)
"Really a nice place. Great for an overnight stop in the Hudson Valley"
The price is CA $191
CA $331 total
includes taxes & fees
Sep 1 - Sep 2
Cabin in the Heart of the Hudson Valley, Cabin 1

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.2 out of 10, Wonderful, (11)
"The house was everything that it is advertised to be. When we arrived, we found it very clean and spacious enough for five adults and two dogs. The hosts were considerate and extremely gracious. The farm is picturesque, chickens and goats look very well cared for and added to the charm. …no worries if you are not an animal lover, the goats and chickens stay far enough away that you can simply not take any notice of them. The beautiful village of Millbrook is just 4 minutes down the road...
Pet-friendly Cottage at Historic Millbrook Farm Estate

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (80)
"Great place! Loved waking up to a water view. Very peaceful."
Lakefront Fall Foliage in New England Just 2 Hours From NYC

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

10.0 out of 10, Exceptional, (11)
"The house worked very well for our family holiday. Very clean, had everything we needed "
The price is CA $417
CA $889 total
includes taxes & fees
Sep 3 - Sep 4
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (48)
"Overall rating 5/5. I would recommend this home to other families and would stay again. "
Litchfield County Four Season Country Paradise
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

Find out more about Wingdale

Find out more about Wingdale

Everything you need to know about Wingdale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wingdale vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wingdale vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wingdale vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wingdale. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wingdale vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wingdale vacation rentals we have selected for you start as low as CA $150 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wingdale rentals

At Expedia, we put the best Wingdale vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wingdale rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wingdale vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wingdale. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find vacation rentals in Wingdale?

Yes, we give you a choice of vacation rentals near well known attractions in Wingdale, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Wingdale?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of Wingdale offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Wingdale?

Choose from 3 Expedia vacation rentals in Wingdale for a memorable vacation.

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 vacation rental in Wingdale like?

Vacation rentals are private properties you can stay in for a long or short time in Wingdale. Vacation rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.