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Wingdale Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Wingdale holiday rentals

Private kitchen

Cozy private room with a comfortable Full-size bed and private bathroom.

Cozy private room with a comfortable Full-size bed and private bathroom.
New Milford
The price is HK$635
HK$1,247 total
includes taxes & fees
16 Jul - 17 Jul
Cozy private room with a comfortable Full-size bed and private bathroom.
Internet, bed sheets

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
The price is HK$784
HK$1,452 total
includes taxes & fees
22 Jul - 23 Jul
Welcome to Sweet Abby Rose!
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
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 HK$1,325
HK$2,213 total
includes taxes & fees
12 Jul - 13 Jul
Cabin in the heart of the Hudson Valley, Cabin 3
Private kitchen

Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is HK$2,102
HK$4,444 total
includes taxes & fees
15 Jul - 16 Jul
Amazing 3-bedroom house with AC in adorable Highland
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (35 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is HK$1,324
HK$2,212 total
includes taxes & fees
12 Jul - 13 Jul
Cabin in the Heart of the Hudson Valley, Cabin 1
Interior

Architect-Designed Dome on Private 7-Acre Retreat

Architect-Designed Dome on Private 7-Acre Retreat
Dover Plains
The price is HK$1,940
HK$3,844 total
includes taxes & fees
12 Jul - 13 Jul
Architect-Designed Dome on Private 7-Acre Retreat
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
The price is HK$740
HK$1,008 total
includes taxes & fees
8 Aug - 9 Aug
Cozy One Bedroom Apartment Centrally Located in Southbury
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.
The price is HK$628
HK$1,047 total
includes taxes & fees
22 Jul - 23 Jul
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is HK$862
HK$1,614 total
includes taxes & fees
12 Jul - 13 Jul
Hoppy Hill Farm House
1 bedroom, free WiFi

2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (19 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveller
The price is HK$783
HK$886 total
includes taxes & fees
3 Aug - 4 Aug
2 Queen Beds | Non-Smoking, Kitchen
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is HK$1,175
HK$2,157 total
includes taxes & fees
14 Jul - 15 Jul
The Tipsy Gypsy - Studio Apartment
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.
The price is HK$1,763
HK$3,303 total
includes taxes & fees
23 Jul - 24 Jul
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Interior

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is HK$1,905
HK$2,540 total
includes taxes & fees
12 Jul - 13 Jul
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Property grounds

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (3 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
The price is HK$941
HK$2,158 total
includes taxes & fees
15 Jul - 16 Jul
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Outdoor dining

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (70 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is HK$1,940
HK$2,552 total
includes taxes & fees
14 Jul - 15 Jul
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds

Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is HK$1,350
HK$1,767 total
includes taxes & fees
13 Jul - 14 Jul
Hudson Valley Farm Getaway- West/Llama Lover Lane
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 price is HK$1,685
HK$2,173 total
includes taxes & fees
12 Jul - 13 Jul
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Exterior

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is HK$782
HK$905 total
includes taxes & fees
9 Aug - 10 Aug
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is HK$823
HK$1,569 total
includes taxes & fees
22 Jul - 23 Jul
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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, (18 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is HK$1,299
HK$1,674 total
includes taxes & fees
14 Jul - 15 Jul
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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

Microtel Inn & Suites by Wyndham Bethel/Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

8/10 Good
"The town is inaccesible. No sidewalks to dining or target, both of which were nearby."
Kate 3-night trip
Posted less than an hour ago
Microtel Inn & Suites by Wyndham Bethel/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:

  • 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?

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!: This holiday home rental outside of Wingdale is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games 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 Tymor 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.