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Wingdale Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Wingdale vacation rentals

Private kitchen

Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
$147 nightly
The price is $166
Aug 18 - Aug 19
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (34 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
$115 nightly
The price is $129
Aug 10 - Aug 11
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (11 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
$243 nightly
The price is $275
Jul 26 - Jul 27
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Outdoor dining

The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
$204 nightly
The price is $231
Aug 9 - Aug 10
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
Property grounds

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Danbury
10.0 out of 10, Exceptional, (1 review)
$493 nightly
The price is $558
Jul 27 - Jul 28
Total with taxes and fees
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Outdoor dining

Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (55 reviews)
"Amazing weekend stay! The place was clean, cozy, and thoughtfully prepared. The host was responsive and welcoming. Would definitely book again!"
United States
Kelsey
$1,834 nightly
The price is $2,078
Aug 18 - Aug 19
Total with taxes and fees
Candlewood Lake Retreat with Private Dock
Cookware/dishes/utensils

Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.6 out of 10, Exceptional, (10 reviews)
"Great spot "
United States
Mike P.
$632 nightly
The price is $715
Jul 27 - Jul 28
Total with taxes and fees
Awesome Lake Home with tons of fun!
TV, fireplace, books

The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (2 reviews)
$648 nightly
The price is $733
Aug 9 - Aug 10
Total with taxes and fees
The Little Lake Cabin with hot tub
Internet, bed sheets

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
$170 nightly
The price is $184
Jul 23 - Jul 24
Total with taxes and fees
Welcome to Sweet Abby Rose!
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
$254 nightly
The price is $275
Jul 23 - Jul 24
Total with taxes and fees
The Tipsy Gypsy - Studio Apartment
Exterior

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
$550 nightly
The price is $623
Aug 6 - Aug 7
Total with taxes and fees
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
Smart TV, fireplace, books

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (19 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
$222 nightly
The price is $251
Jul 27 - Jul 28
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Property grounds

Lakefront Summer Stunner in New England Just 2 Hours From NYC

Lakefront Summer Stunner in New England Just 2 Hours From NYC
Sharon
10.0 out of 10, Exceptional, (95 reviews)
"Great location, quiet and beautiful. Loved the trails, picturesque drives between small towns and cozy accommodations. "
United States
Chad J.
$525 nightly
The price is $595
Jul 25 - Jul 26
Total with taxes and fees
Lakefront Summer Stunner in New England Just 2 Hours From NYC
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
$182 nightly
The price is $206
Jul 28 - Jul 29
Total with taxes and fees
Hoppy Hill Farm House
Interior

Architect-Designed Dome on Private 7-Acre Retreat

Architect-Designed Dome on Private 7-Acre Retreat
Dover Plains
$436 nightly
The price is $493
Jul 23 - Jul 24
Total with taxes and fees
Architect-Designed Dome on Private 7-Acre Retreat
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
$254 nightly
The price is $275
Jul 28 - Jul 29
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC
Property grounds

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (8 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
$118 nightly
The price is $134
Jul 27 - Jul 28
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
TV, fireplace

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$399 nightly
The price is $432
Jul 28 - Jul 29
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Coffee/tea maker, fridge, microwave, oven

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
$550 nightly
The price is $622
Aug 10 - Aug 11
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
Smart TV, fireplace, video games, DVD player

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
$902 nightly
The price is $978
Jul 23 - Jul 24
Total with taxes and fees
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
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

Best Western Danbury/Bethel

Best Western Danbury/Bethel

10/10 Excellent
"Excellent experience"
Jaydelle 2-night trip
Posted 2 hours ago
Best Western Danbury/Bethel

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Wingdale in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $108 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Lakefront Summer Stunner in New England Just 2 Hours From NYC: This vacation home rental outside of Wingdale is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a private yard 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 Whaley Lake. 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.