Wingdale Holiday Rentals, New York: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Wingdale

Pet friendly

Apartment

Pool

Spa

Hot tub

Family friendly

Cottage

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Wingdale hotels

A hotel room with two beds, a desk, a chair, and a window with curtains.

A modern living room with a television mounted on the wall, a small cabinet with a vase of flowers, and two red armchairs.

A two-story motel with a central patio and a parking lot.

A hotel room with a TV mounted on the wall displaying a sports game, a small refrigerator, a microwave, and a coffee maker on a shelf.

1. Rocky River Inn

New Milford

Nancy

฿4,996

฿5,745 total

includes taxes & fees

14 Oct - 15 Oct

A two-story house with a porch, white railings, and a blue door.

A staircase with wooden balusters leading to a landing.

A modern living room with a sofa, coffee table, and a dining area with a table and chairs.

A modern kitchen with grey cabinetry, a stainless steel refrigerator, a built-in oven, and a coffee maker.

2. Station Inn Pawling

Pawling

Fang

฿4,764

฿5,389 total

includes taxes & fees

11 Nov - 12 Nov

A hotel room with a bed, a TV on a wooden stand, a dining area with chairs, and a patterned carpet.

Two HP desktop computers on a desk with a lamp, keyboard, and mouse.

A modern living room with a dining area, a TV mounted on the wall, and a patterned carpet.

A spacious conference room with multiple tables and chairs, large windows, and a carpeted floor.

3. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

Bernadette

฿2,917

฿3,387 total

includes taxes & fees

9 Nov - 10 Nov

A large white building with green shutters, a covered patio with red umbrellas, and a well-maintained garden.

A wooden dining table with chairs, a vase of flowers, and a cabinet with glass doors containing bottles.

A dining area with a wooden table, a Christmas tree, and a fireplace.

A neatly arranged bedroom with a large bed, a bedside table with a lamp, a chair, and a framed picture on the wall.

4. Le Chambord at Curry Estate

Hopewell Junction

Theresa

฿7,008

฿7,928 total

includes taxes & fees

13 Oct - 14 Oct

A modern hotel lobby with wooden flooring, yellow chairs, a long dining table, and pendant lighting.

An indoor swimming pool with clear water, a lifeguard chair, and a sunlit area with lounge chairs.

A reception area with a wooden floor, a reception desk, and a wall with a welcome sign.

A hotel room with a large bed, a sofa, a desk, and a TV. There are windows with curtains, a lamp, and a picture on the wall.

5. Hampton Inn & Suites Poughkeepsie

Crown Heights

Sanford

฿3,272

฿3,799 total

includes taxes & fees

8 Nov - 9 Nov

A modern hotel with a prominent 'Hyatt Place' sign, outdoor seating area, and a covered entrance.

A modern bar area with round tables and patterned chairs, a bar counter with a TV, and shelves with bottles.

A modern hotel room with a wooden desk, a flat-screen TV, and a large abstract painting. There is a sofa and a coffee table in the living area.

A modern bar area with round tables and chairs, a bar counter with a variety of bottles, and a large screen mounted on the wall.

6. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

Jacqueline Sue

฿2,783

฿3,232 total

includes taxes & fees

12 Nov - 13 Nov

A living room with a fireplace, a piano, and a sofa.

A bedroom with a bed, a fireplace, a TV, and a view of the outdoors.

A modern kitchen with white cabinets, a black countertop, and a built-in oven.

7. The Kent Collection - The Firefly Inn

Kent

Candice Burrows

฿10,683

฿12,285 total

includes taxes & fees

26 Oct - 27 Oct

A hotel room with a bed, a chair, a small table with a plant, and a mirror.

A hotel lobby with seating areas, a reception desk, and a large window offering a view.

A hotel room with a sofa, ottoman, bedside table, lamp, air conditioning unit, and a painting on the wall.

A compact hotel room with a kitchenette, a bed, and a view of the outdoors.

8. La Quinta Inn & Suites by Wyndham Danbury

Danbury

Steven

฿3,889

฿4,473 total

includes taxes & fees

25 Oct - 26 Oct

A modern building with large windows, outdoor seating, and a well-maintained garden.

A modern living room with a sectional sofa, a glass coffee table, and a flat-screen TV mounted on the wall.

A modern bar area with a long counter, three stools, a variety of bottles, and a menu board.

A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and landscaped surroundings.

9. Courtyard By Marriott Danbury

Danbury

Julie

฿3,729

฿4,288 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a desk, a chair, a TV, and a window with curtains.

A room with a dining table, four wooden stools, a window with blinds, and a view of the outside.

A modern dining area with white tables and chairs, a counter with a coffee machine, and a blue accent wall.

A modern hotel room with a dining area, a TV, and a large window with curtains.

10. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

Tara

฿3,561

฿4,095 total

includes taxes & fees

13 Oct - 14 Oct

An outdoor seating area with stone walls, a fire feature, and yellow chairs.

An indoor swimming pool with clear water, surrounded by green and red chairs, and a tiled floor.

A hotel room with two single beds, a sofa, a desk, and a chair.

A modern indoor seating area with a sofa, tables, and chairs, featuring large windows and a clean, contemporary design.

11. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

Roy

฿3,822

฿4,438 total

includes taxes & fees

9 Nov - 10 Nov

A courtyard with a fire pit, outdoor seating, and a covered area with string lights.

A gym with exercise equipment, dumbbells, treadmills, and a bench.

A spacious hotel lobby with a high ceiling, wooden beams, and a large seating area with sofas and round tables.

A hotel lobby with a reception desk, seating area, and a stone fireplace.

12. Homewood Suites by Hilton Poughkeepsie

Poughkeepsie

Tammie

฿4,097

฿4,757 total

includes taxes & fees

1 Nov - 2 Nov

A modern dining area with multiple tables and chairs, a kitchen area with appliances, and a seating area with a large window.

A large, multi-story hotel with a prominent entrance and a parking lot.

A modern room with a wooden wardrobe, a white shelf, and a yellow office chair.

A self-service snack and beverage area with refrigerated drink dispensers and shelves stocked with various snacks and beverages.

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

Danbury

Jay

฿3,957

฿4,550 total

includes taxes & fees

8 Nov - 9 Nov

A hotel reception area with a reception desk, a waiting area with sofas, and a glass door entrance.

A modern kitchen with a central island, a dining area with chairs, and a refrigerator.

A hotel corridor with a vending machine, a refrigerator, and a door.

A hotel room with two beds, a desk, a chair, and a TV.

14. Quality Inn Poughkeepsie

Arlington

stacey

฿3,107

฿3,607 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a large window with a forest view.

A hot tub with a view of trees through large windows.

A Hampton Inn hotel with a modern design, featuring a central entrance, multiple floors, and a parking lot.

A snack display with various chips and snacks, a refrigerated beverage area, and framed pictures on the wall.

15. Hampton Inn Danbury

Danbury

Lucineia

฿4,817

฿5,539 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio area with a stone fire pit, seating, and a Marriott sign in the background.

A hotel with multiple buildings, a parking lot, and a body of water in the foreground.

A spacious lobby with a fireplace, seating area, and a reception desk.

A modern hotel room with a large bed, a desk, and a chair. There is a window with curtains, a wall-mounted lamp, and a mirror.

16. SpringHill Suites by Marriott Fishkill

Fishkill

Aleksandar

฿6,002

฿6,940 total

includes taxes & fees

13 Oct - 14 Oct

A spacious lobby with a high ceiling, a reception desk, a seating area with blue sofas and armchairs, and a visible Pepsi refrigerator.

A hotel room with a sofa, ottoman, a bed with a red blanket, a chair, and framed pictures on the wall.

An indoor swimming pool with a stone wall, blue chairs, and a lifeguard chair.

A modern breakfast bar with a wooden wall, a coffee machine, and a juice dispenser.

17. Comfort Suites Fishkill near Interstate 84

Fishkill

Daniel

฿3,520

฿4,070 total

includes taxes & fees

11 Nov - 12 Nov

A spacious living room with hardwood floors, a large dining area, and a cozy seating area with a red sofa and matching cushions.

A corner room with two white upholstered chairs, a glass table, and a vase with white flowers.

A four-poster bed with a canopy, a sitting area with a chair and a table, and a view of the outdoors through large windows.

A spacious foyer with a wooden ceiling, a large chandelier, a fireplace, and a traditional wooden dresser with drawers.

18. Homestead Inn

New Milford

Priscilla

฿6,902

฿7,938 total

includes taxes & fees

1 Nov - 2 Nov

A large, modern hotel with a covered entrance, well-maintained lawns, and a clear sky.

A Hilton Garden Inn sign with the words "ENTRANCE" below it, surrounded by well-maintained hedges and colorful flower beds.

A modern kitchen with a bar area, featuring a marble countertop, wine bottles, glasses, and a flat-screen TV.

A spacious lobby with a central reception desk, seating areas, and a vending machine.

19. Hilton Garden Inn Danbury

Danbury

Kathryn

฿3,705

฿4,261 total

includes taxes & fees

1 Nov - 2 Nov

A patio area with outdoor seating and a fire pit, surrounded by buildings with a brick facade and a covered seating area.

A hotel room with a flat-screen TV, a sofa, a small table, a lamp, a cabinet, and a door.

A Best Western hotel with a parking lot and a rainbow in the background.

A hotel room with a large bed, a nightstand, a wall-mounted lamp, and a window with curtains.

20. Best Western Fishkill Inn & Suites

Fishkill

Taedmary

฿3,893

฿4,501 total

includes taxes & fees

11 Nov - 12 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Wingdale attractions

Harlem Valley Golf Club

Enjoy a round of golf in Wingdale at Harlem Valley Golf Club.

See properties

Pawling Nature Reserve

You can take time to visit Pawling Nature Reserve during your travels to Wingdale.

See properties

Dover Veterans Memorial Library

After visiting Dover Veterans Memorial Library, make a plan to see the other sights and activities in Wingdale.

See properties

Leather Hill Preserve

You can take time to visit Leather Hill Preserve during your travels to Wingdale.

See properties

Olivet University

Walk around the campus at Olivet University as part of your travels around Wingdale.

See properties

Learn more about Wingdale

Venture to sights like Dover Veterans Memorial Library and Harlem Valley Golf Club as you discover Wingdale.

See all hotels in Wingdale

A weathered window with a view of trees and a building in the background.

Top Wingdale Hotel Reviews

Comfort Inn & Suites Danbury-Bethel

8/10 Good

"Easy access"

Courtyard by Marriott Poughkeepsie

8/10 Good

"There was several mixups about this reservation. I was charged $10 a day for parking which I never knew of $30 total. Also bottles of water in the room with five dollar tags marked on them.Then breakfast was not complementary you had to pay for that as well. Staff did not know how to split the charge for two people. Said they did it but I have a full charge on my credit card which was reserved through Expedia. ever since Bonvoy took over apparently things have changed from the old Marriott. I’ve used for 50 years and loved. Hampton Inn in Albany gave us a bottle of water upon registration, had a wonderful buffet breakfast complementary and did not charge for parking lots that you drive in and out of yourself"

Hampton Inn & Suites Poughkeepsie

10/10 Excellent

"Rockstars! Staff really cares, definitely can tell its a corporate hotel, not franchised"

Home2 Suites By Hilton Poughkeepsie

10/10 Excellent

"Great place to stay in Poughkeepsie My only comment is to please improve the Breakfast flow Access is very difficult to quickly move from one station to another"

Holiday Inn Express Poughkeepsie by IHG

8/10 Good

"The place was clean and the breakfast good. It was quite expensive though."

Best Western Fishkill Inn & Suites

10/10 Excellent

"The staff was very friendly and helpful. We booked last minute and was surprised by the size of the room! The kitchen staff in the morning were amazing!!! They were very attentive and were constantly refilling coffee and items getting low."

Best Western Danbury/Bethel

8/10 Good

"The room was efficient as expected. The room was clean and neat. TV was interesting to say the least to use, maybe put out some directions. Honestly, a good stay and really no major complaint."

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent

"Guest room was designed well. Very clean. Comfortable bed. Great shower, strong pressure, like a massage. Breakfast was excellent , fresh and hot. Will be back"

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"Good breakfast. Friendly helpful staff."

More cheap stays in Wingdale

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY

฿2,917

฿3,387 total

9 Nov - 10 Nov

includes taxes & fees

8.6/10 Excellent! (1,010 reviews)

Quality Inn Poughkeepsie

536 Haight Ave, Building A Poughkeepsie NY

฿3,107

฿3,607 total

1 Nov - 2 Nov

includes taxes & fees

7.6/10 Good! (603 reviews)

Best Western Danbury/Bethel

11 Stony Hill Road Bethel CT

฿3,363

฿3,868 total

1 Nov - 2 Nov

includes taxes & fees

7.8/10 Good! (1,002 reviews)

Comfort Suites Fishkill near Interstate 84

835 Route 52 Fishkill NY

฿3,520

฿4,070 total

11 Nov - 12 Nov

includes taxes & fees

9.2/10 Wonderful! (1,007 reviews)

Microtel Inn & Suites by Wyndham Bethel/Danbury

80 Benedict Rd Bethel CT

฿3,561

฿4,095 total

13 Oct - 14 Oct

includes taxes & fees

8.2/10 Very good! (1,008 reviews)

Comfort Inn & Suites Danbury-Bethel

80 Newtown Road Danbury CT

฿3,859

฿4,437 total

8 Nov - 9 Nov

includes taxes & fees

8.4/10 Very good! (920 reviews)

Frequently asked questions

Where is the best place to stay in Wingdale?

Ethan Allen Hotel, located 18.7 mi (30 km) from the heart of Wingdale, is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Quality Inn Poughkeepsie and Hyatt Place Poughkeepsie / Hudson Valley. See all available top hotels, or vacation rentals in Wingdale.

If I need to cancel my hotel reservation in Wingdale, will I receive a refund?

Yes, you'll find most hotel room reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Wingdale.

What is staying in Wingdale like?

Those travelling to Wingdale will definitely enjoy the sights to see and things to do. In Wingdale, there are 4 hotels and other accommodation options to choose from. Find out more about Wingdale.

What are the top places to visit in Wingdale?

Favourite places to visit include Dover Veterans Memorial Library, Harlem Valley Golf Club and Leather Hill Preserve. A couple of additional sights to add to your itinerary are Pawling Nature Reserve and West Mountain State Forest. Take a look at what more there is to see and do in Expedia's Wingdale guide.

What's the seasonal weather in Wingdale?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Wingdale are January, February, March and April, with each month seeing an average of 17 cm of snowfall.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Wingdale on Expedia.com

Find hotels in Wingdale, NY from ฿2,741

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Wingdale

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Wingdale hotels

1. Rocky River Inn

2. Station Inn Pawling

3. Holiday Inn Express Poughkeepsie by IHG

4. Le Chambord at Curry Estate

5. Hampton Inn & Suites Poughkeepsie

6. Hyatt Place Poughkeepsie / Hudson Valley

7. The Kent Collection - The Firefly Inn

8. La Quinta Inn & Suites by Wyndham Danbury

9. Courtyard By Marriott Danbury

10. Microtel Inn & Suites by Wyndham Bethel/Danbury

11. Home2 Suites By Hilton Poughkeepsie

12. Homewood Suites by Hilton Poughkeepsie

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

14. Quality Inn Poughkeepsie

15. Hampton Inn Danbury

16. SpringHill Suites by Marriott Fishkill

17. Comfort Suites Fishkill near Interstate 84

18. Homestead Inn

19. Hilton Garden Inn Danbury

20. Best Western Fishkill Inn & Suites

Stay near popular Wingdale attractions

Harlem Valley Golf Club

Pawling Nature Reserve

Dover Veterans Memorial Library

Leather Hill Preserve

Olivet University

Learn more about Wingdale

Top Wingdale Hotel Reviews

Comfort Inn & Suites Danbury-Bethel

Courtyard by Marriott Poughkeepsie

Hampton Inn & Suites Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

Holiday Inn Express Poughkeepsie by IHG

Best Western Fishkill Inn & Suites

Best Western Danbury/Bethel

Hyatt Place Poughkeepsie / Hudson Valley

Quality Inn Hyde Park Poughkeepsie North

More cheap stays in Wingdale

Holiday Inn Express Poughkeepsie by IHG

Quality Inn Poughkeepsie

Best Western Danbury/Bethel

Comfort Suites Fishkill near Interstate 84

Microtel Inn & Suites by Wyndham Bethel/Danbury

Comfort Inn & Suites Danbury-Bethel

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app