Wingdale Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Wingdale vacation rentals

Exterior

Apartment in Millbrook

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
10.0 out of 10, Exceptional, (2 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is ￥50,870
￥78,048 total
includes taxes & fees
Mar 15 - Mar 16
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Exterior

Cottage in Verbank

Waterfall Sound & Beach-Inspired Country Wing
10.0 out of 10, Exceptional, (7 reviews)
"Our host was very welcoming and responsive; he took extra care to ensure our stay was comfortable. Our experience with the property and host exceeded our expectations. We were extremely pleased and would stay at this property again and recommend it to others."
United States
Kathleen B.
The price is ￥33,174
￥51,584 total
includes taxes & fees
Mar 14 - Mar 15
Waterfall Sound & Beach-Inspired Country Wing
Terrace/patio

Cabin in Newburgh

Cabin in the heart of the Hudson Valley, Cabin 3
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is ￥26,866
￥44,880 total
includes taxes & fees
Mar 16 - Mar 17
Cabin in the heart of the Hudson Valley, Cabin 3
Smart TV, fireplace, video games, DVD player

Vacation Home in Carmel Hamlet

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
10.0 out of 10, Exceptional, (19 reviews)
"Lovely house with all the amenities. We had a wonderful time."
United States
Diana P.
The price is ￥85,879
￥155,738 total
includes taxes & fees
Mar 15 - Mar 16
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Smart TV, fireplace, books

Apartment in Kent

Mid Century Modern Studio w/ Full Kitchen - Newly Built
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥27,820
￥35,649 total
includes taxes & fees
Mar 25 - Mar 26
Mid Century Modern Studio w/ Full Kitchen - Newly Built
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in Newburgh

Cabin in the Heart of the Hudson Valley, Cabin 1
10.0 out of 10, Exceptional, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is ￥26,866
￥44,880 total
includes taxes & fees
Mar 16 - Mar 17
Cabin in the Heart of the Hudson Valley, Cabin 1
Private kitchen

Apartment in Carmel Hamlet

Charming 1-bedroom apartment in Carmel with WiFi, AC
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
The price is ￥21,461
￥44,276 total
includes taxes & fees
Mar 15 - Mar 16
Charming 1-bedroom apartment in Carmel with WiFi, AC
Exterior

Apartment in Salisbury

Dugway Hideaway Walking Distance to Lime Rock Park
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is ￥31,794
￥50,076 total
includes taxes & fees
Mar 15 - Mar 16
Dugway Hideaway Walking Distance to Lime Rock Park
Dining

Vacation Home in Goshen

Whispering Estate Guest House - Countryside Getaway
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ￥85,844
￥140,132 total
includes taxes & fees
Mar 14 - Mar 15
Whispering Estate Guest House - Countryside Getaway
Outdoor dining

Vacation Home in Fishkill

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.4 out of 10, Exceptional, (62 reviews)
"Best place ever, various entertainment options from projector to tvs. "
United States
Mahbub Ridhoo M.
The price is ￥39,345
￥51,376 total
includes taxes & fees
Mar 16 - Mar 17
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Cottage (3 Bedrooms) | Interior

Cottage in New Preston

Dainty New Preston Cottage w/ Dock & Lake Views!
3.0 star property
The price is ￥34,090
￥82,342 total
includes taxes & fees
Apr 10 - Apr 11
Dainty New Preston Cottage w/ Dock & Lake Views!
Exterior

Apartment in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥14,519
￥19,883 total
includes taxes & fees
Mar 16 - Mar 17
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

Vacation Home in Poughkeepsie

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
10.0 out of 10, Exceptional, (2 reviews)
"Great host"
United States
Lindsey F.
The price is ￥37,970
￥107,964 total
includes taxes & fees
Mar 14 - Mar 15
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Exterior detail

Apartment in New Fairfield

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
10.0 out of 10, Exceptional, (35 reviews)
"Stunning property!!"
United States
Samantha
The price is ￥43,717
￥76,028 total
includes taxes & fees
Mar 16 - Mar 17
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Exterior

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is ￥42,127
￥94,388 total
includes taxes & fees
Mar 14 - Mar 15
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Exterior

Cabin in Fishkill

Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥48,088
￥72,773 total
includes taxes & fees
Mar 17 - Mar 18
Rustic Cabin in Fishkill!
TV, fireplace

Vacation Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (13 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is ￥26,469
￥55,389 total
includes taxes & fees
Mar 25 - Mar 26
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Fridge, microwave, oven, stovetop

Vacation Home in Holmes

"Country outside the city " 3 bedrooms 2 full bathrooms
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is ￥38,057
￥99,162 total
includes taxes & fees
Mar 15 - Mar 16
"Country outside the city " 3 bedrooms 2 full bathrooms
Fridge, microwave, oven, stovetop

Vacation Home in New Fairfield

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
10.0 out of 10, Exceptional, (18 reviews)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
The price is ￥30,560
￥79,497 total
includes taxes & fees
Mar 17 - Mar 18
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Cookware/dishes/utensils

Vacation Home in New Fairfield

Awesome Lake Home with tons of fun!
9.8 out of 10, Exceptional, (7 reviews)
"Great spot "
United States
Mike P.
The price is ￥64,383
￥112,750 total
includes taxes & fees
Mar 17 - Mar 18
Awesome Lake Home with tons of fun!
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

Hampton Inn Danbury

Hampton Inn Danbury

10/10 Excellent
"Clean"
Troy 1-night trip
Posted 8 hours ago
Hampton Inn Danbury

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:

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

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Wingdale offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and an electric kettle, 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.