Wingdale Holiday Rentals, New York: Private House Rentals

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Our top choices for Wingdale hotels

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

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

A bathroom with three sinks, a large mirror, and a door leading to another room.

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

฿5,009

฿5,760 total

includes taxes & fees

12 Oct - 13 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

฿5,168

฿5,846 total

includes taxes & fees

8 Nov - 9 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 lobby with a wooden bench, a reception desk, and a colorful artwork on the wall.

3. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

Bernadette

฿2,927

฿3,399 total

includes taxes & fees

8 Nov - 9 Nov

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

A gazebo with a white porch and a lawn party setup with rows of chairs.

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

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

4. Le Chambord at Curry Estate

Hopewell Junction

Tracy

฿7,026

฿7,948 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

A swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple windows.

5. La Quinta Inn & Suites by Wyndham Danbury

Danbury

Steven

฿3,900

฿4,485 total

includes taxes & fees

11 Oct - 12 Oct

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

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.

A snack display area with shelves stocked with various snacks and a large wall advertisement for treats.

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

6. Hampton Inn & Suites Poughkeepsie

Crown Heights

Sanford

฿3,283

฿3,812 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 reception area with a geometric patterned wall, a reception desk, a sofa, and a dining area with chairs and a table.

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 patterned chairs, a bar counter with a TV, and shelves with bottles.

7. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

Jacqueline Sue

฿3,163

฿3,673 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A white house with a porch, two flower planters, and a well-maintained lawn.

8. The Kent Collection - The Firefly Inn

Kent

Candice Burrows

฿10,719

฿12,327 total

includes taxes & fees

15 Oct - 16 Oct

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

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

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

A modern indoor swimming pool with clear water, surrounded by lounge chairs and a sunlit area with large windows.

9. Courtyard By Marriott Danbury

Danbury

Julie

฿3,741

฿4,303 total

includes taxes & fees

1 Nov - 2 Nov

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.

10. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

Deborah

฿3,835

฿4,453 total

includes taxes & fees

3 Nov - 4 Nov

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

A hotel with a row of parked cars in front, a covered parking area, and a sunset sky.

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

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

11. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

Tara

฿3,358

฿3,862 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

A modern lounge area with a stone wall, a flat-screen TV, and blue seating.

12. Comfort Suites Fishkill near Interstate 84

Fishkill

Daniel

฿3,289

฿3,803 total

includes taxes & fees

8 Nov - 9 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 self-service snack and beverage area with refrigerated drink dispensers and shelves stocked with various snacks and beverages.

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

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

Danbury

Jay

฿3,465

฿3,985 total

includes taxes & fees

8 Nov - 9 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 large bed, a nightstand, a wall-mounted lamp, and a window with curtains.

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

A spacious living area with a dining table and chairs, a sofa, and a kitchen in the background.

14. Best Western Fishkill Inn & Suites

Fishkill

Taedmary

฿4,209

฿4,867 total

includes taxes & fees

8 Nov - 9 Nov

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

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

A hotel courtyard with outdoor seating, a fire pit, and a tennis court.

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

15. Homewood Suites by Hilton Poughkeepsie

Poughkeepsie

Tammie

฿4,111

฿4,774 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 snack display with various chips and snacks, a refrigerated beverage area, and framed pictures on the wall.

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

A modern lounge area with a sofa and two armchairs, a coffee table, and a wall with a black and white abstract design.

16. Hampton Inn Danbury

Danbury

Lucineia

฿4,833

฿5,558 total

includes taxes & fees

1 Nov - 2 Nov

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

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

An indoor swimming pool with clear pool rules, a lifeguard chair, and a poolside area with lounge chairs.

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

17. Quality Inn Poughkeepsie

Arlington

Dawn

฿3,117

฿3,620 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 spacious lobby with a fireplace, comfortable seating, and a high ceiling with skylights.

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.

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

18. SpringHill Suites by Marriott Fishkill

Fishkill

Aleksandar

฿6,022

฿6,964 total

includes taxes & fees

12 Oct - 13 Oct

A hotel room with a green sofa, a small table, a bed with a headboard, a desk with a lamp, and a framed picture on the wall.

A restaurant with multiple tables and chairs, a kitchen area, and a microwave.

A rack of black hexagonal dumbbells with visible weight markings, arranged on a metal stand in a gym setting.

A spacious living area with sofas, a fireplace, and artwork on the walls.

19. Quality Inn & Suites Fishkill South near I-84

Fishkill

William

฿3,569

฿4,127 total

includes taxes & fees

2 Nov - 3 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 spacious foyer with a wooden ceiling, a large chandelier, a fireplace, and a traditional wooden dresser with drawers.

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

20. Homestead Inn

New Milford

Priscilla

฿6,926

฿7,965 total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Wingdale attractions

Harlem Valley Golf Club

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

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Dover Veterans Memorial Library

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

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Leather Hill Preserve

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

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Olivet University

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

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Pawling Nature Reserve

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

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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

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"Just issues with the tv and the WiFi."

Hampton Inn & Suites Poughkeepsie

10/10 Excellent

"Great hotel, clean and confortable"

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent

"great time"

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent

"Very clean and quiet hotel. The bed was vey comfortable, spacious and clean. I only stayed for 1 night but will definitely come back."

SureStay Plus Hotel by Best Western Highland Poughkeepsie

8/10 Good

"The room was clean and the bed was very comfortable. Was there for Parent weekend and the location was perfect and the price was good for being on that particular weekend."

Heritage Hotel, Golf & Conference Center

8/10 Good

"Beds were great. Bathroom clean, but shower was slippery. TV remote was almost useless. Support staff were helpful. Location was excellent. Parking was great for early arrivals, but an extended wait for late arrivals. I did not eat breakfast on the premises. Small shopping plaza a mile away with TJMaxx. Other restaurants nearby. One mile from I-84."

Best Western Danbury/Bethel

10/10 Excellent

"very clean, staff was pleasant and professional"

Home2 Suites By Hilton Poughkeepsie

10/10 Excellent

"Perfect. Lovely room. 10 stars"

Studio 6 Extended Stay Fishkill Westage Center NY

10/10 Excellent

"Wonderful staff"

More cheap stays in Wingdale

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY

฿2,927

฿3,399 total

8 Nov - 9 Nov

includes taxes & fees

8.6/10 Excellent! (1,004 reviews)

Quality Inn Poughkeepsie

536 Haight Ave, Building A Poughkeepsie NY

฿3,117

฿3,620 total

1 Nov - 2 Nov

includes taxes & fees

7.6/10 Good! (600 reviews)

Comfort Suites Fishkill near Interstate 84

835 Route 52 Fishkill NY

฿3,289

฿3,803 total

8 Nov - 9 Nov

includes taxes & fees

Microtel Inn & Suites by Wyndham Bethel/Danbury

80 Benedict Rd Bethel CT

฿3,358

฿3,862 total

11 Oct - 12 Oct

includes taxes & fees

Best Western Danbury/Bethel

11 Stony Hill Road Bethel CT

฿3,375

฿3,881 total

1 Nov - 2 Nov

includes taxes & fees

Comfort Inn & Suites Danbury-Bethel

80 Newtown Road Danbury CT

฿3,942

฿4,533 total

8 Nov - 9 Nov

includes taxes & fees

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.

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Book Hotels in Wingdale on Expedia.com

Find hotels in Wingdale, NY from ฿2,750

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. La Quinta Inn & Suites by Wyndham Danbury

6. Hampton Inn & Suites Poughkeepsie

7. Hyatt Place Poughkeepsie / Hudson Valley

8. The Kent Collection - The Firefly Inn

9. Courtyard By Marriott Danbury

10. Home2 Suites By Hilton Poughkeepsie

11. Microtel Inn & Suites by Wyndham Bethel/Danbury

12. Comfort Suites Fishkill near Interstate 84

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

14. Best Western Fishkill Inn & Suites

15. Homewood Suites by Hilton Poughkeepsie

16. Hampton Inn Danbury

17. Quality Inn Poughkeepsie

18. SpringHill Suites by Marriott Fishkill

19. Quality Inn & Suites Fishkill South near I-84

20. Homestead Inn

Stay near popular Wingdale attractions

Harlem Valley Golf Club

Dover Veterans Memorial Library

Leather Hill Preserve

Olivet University

Pawling Nature Reserve

Learn more about Wingdale

Top Wingdale Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

Hampton Inn & Suites Poughkeepsie

Holiday Inn Express Poughkeepsie by IHG

DoubleTree by Hilton Poughkeepsie Convention Center

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Heritage Hotel, Golf & Conference Center

Best Western Danbury/Bethel

Home2 Suites By Hilton Poughkeepsie

Studio 6 Extended Stay Fishkill Westage Center NY

More cheap stays in Wingdale

Holiday Inn Express Poughkeepsie by IHG

Quality Inn Poughkeepsie

Comfort Suites Fishkill near Interstate 84

Microtel Inn & Suites by Wyndham Bethel/Danbury

Best Western Danbury/Bethel

Comfort Inn & Suites Danbury-Bethel

Frequently asked questions

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