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Hotels in Wingdale

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Dates

November 2026

December 2026

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Where to stay in Wingdale?

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

1. Rocky River Inn

New Milford

$171 total

includes taxes & fees

Nov 1 - Nov 2

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

2. Station Inn Pawling

Pawling

$179 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a bed, two bedside lamps, a desk with a chair, a small refrigerator, and a door leading to the bathroom.

3. Maple Leaf Motel

New Milford

$102 total

includes taxes & fees

Nov 1 - Nov 2

A covered outdoor seating area with brick flooring and metal railings, overlooking a river.

4. Best Western Plus The Inn & Suites At The Falls

Red Oaks Mill

$118 total

includes taxes & fees

Nov 2 - Nov 3

A hotel entrance with a brick facade, a glass door entrance, and a paved walkway.

5. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

$106 total

includes taxes & fees

Nov 29 - Nov 30

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

6. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

$113 total

includes taxes & fees

Nov 23 - Nov 24

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

7. Hampton Inn & Suites Poughkeepsie

Crown Heights

$123 total

includes taxes & fees

Nov 4 - Nov 5

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

8. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

$109 total

includes taxes & fees

Nov 29 - Nov 30

A garden with a variety of plants and flowers, a white picket fence, and a small table with chairs.

9. Millbrook Country House Bed & Breakfast

Millbrook

$272 total

includes taxes & fees

Oct 30 - Oct 31

A building entrance with a covered porch, stone pillars, and a mailbox.

10. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

$82 total

includes taxes & fees

Nov 24 - Nov 25

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

11. Homestead Inn

New Milford

$237 total

includes taxes & fees

Nov 1 - Nov 2

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

12. Le Chambord at Curry Estate

Hopewell Junction

$236 total

includes taxes & fees

Nov 1 - Nov 2

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

13. Courtyard By Marriott Danbury

Danbury

$128 total

includes taxes & fees

Nov 15 - Nov 16

A modern gym with treadmills, elliptical machines, and weightlifting equipment.

14. DoubleTree by Hilton Poughkeepsie Convention Center

Downtown Poughkeepsie

$129 total

includes taxes & fees

Nov 4 - Nov 5

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

15. Quality Inn Poughkeepsie

Arlington

$108 total

includes taxes & fees

Nov 18 - Nov 19

A covered garden area with a brick building in the background, a central pathway, and various plants and flowers.

16. Ethan Allen Hotel

Danbury

$134 total

includes taxes & fees

Nov 8 - Nov 9

A spacious room with a curved ceiling, a wooden bench, a sofa, and a dining table with chairs.

17. Heidi's Inn

Brewster

$141 total

includes taxes & fees

Nov 1 - Nov 2

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

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

Danbury

$154 total

includes taxes & fees

Nov 29 - Nov 30

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

19. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

$131 total

includes taxes & fees

Nov 1 - Nov 2

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

20. La Quinta Inn & Suites by Wyndham Danbury

Danbury

$137 total

includes taxes & fees

Nov 8 - Nov 9

View all properties

Go beyond your typical stay in Wingdale

Top landmarks in Wingdale

Pawling Nature Reserve

Pawling Nature Reserve is 1.8 mi (3 km) from central Wingdale, why not stop by during your stay.

See properties

Learn more about Wingdale

Wingdale is well-known for its attractions such as Dover Veterans Memorial Library and Harlem Valley Golf Club.

See all hotels in Wingdale

Check out reviews of Wingdale hotels guests love

Rocky River Inn

New Milford

10/10 Exceptional

Zoe

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

10/10 Exceptional

Comfy. Homey. Clean. Brightly lit and cheery lobby area. Great breakfast setup. Nice bedding. Spacious suite style. Easy and quick drive to Marist. Very small downers: Parking lot a tad cramped and narrow. Muddy construction lot in front. Desk staff tends to stray away from the desk and there was no telling when they would be back. Could use a desk sign or something saying "Back in 15 minutes."

David

Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

10/10 Exceptional

It was a special stay for us, Marist graduation weekend 2025. Unfortunately, there was a mixup with our reservation. The fabulous front desk staff did not let us down, Kat, Julia & Tianna went above & beyond to “fix” the situation quickly! In addition, Jason, the hotel manager made sure we were super comfortable & had an enjoyable weekend with our son! Hotel was super clean, comfortable & breakfast was great! I would highly recommend this well run Hyatt!

Richard

Homestead Inn

New Milford

10/10 Exceptional

This is my second time staying at the Inn, and everytime that out do themselves from the time before. Gave me a call to see if there was anything special I may need prior to my arrival. Room is spotless, probably the cleanest room I have ever experience. Convenient to the New Milford Green, plenty of good places to eat. Very quiet and restful. I will be staying at the end at least once a month over the next year, Highly recommend!!!

Bob

Hampton Inn & Suites Poughkeepsie

Crown Heights

10/10 Exceptional

Andrew

Le Chambord at Curry Estate

Hopewell Junction

10/10 Exceptional

Beautiful property ! Anyone looking for wedding venue, check this place out ! When I walked in the door I was greeted and welcomed! The inside had old charm with beautiful woodworking, dining area was so charming , with white table cloths , beautiful windows i just wanted to sit there all day with a hot chocolate or a cup of tea ! The bedroom looked like it was recently redone with some beautiful older pieces of furniture but was spotless! towels were nice and thick! The bed was very very...

ChrisL

Millbrook Country House Bed & Breakfast

Millbrook

10/10 Exceptional

Anonymous traveler

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

Comfort Suites Fishkill near Interstate 84

Fishkill

10/10 Exceptional

Wendy

Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

10/10 Exceptional

Leslie

A multi-story hotel with a central entrance, stone pillars, and a brick facade.

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Hyde Park

10/10 Exceptional

Sheri

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

Danbury

10/10 Exceptional

Robert

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.

Quality Inn & Suites Fishkill South near I-84

Fishkill

10/10 Exceptional

Lynn

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

Best Western Fishkill Inn & Suites

Fishkill

10/10 Exceptional

MHD Amar

Frequently Asked Questions

Can I book a refundable hotel in Wingdale?

If you're looking for the flexibility to change your plans to Wingdale, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Wingdale be like during my visit?

The warmest months in Wingdale are usually July and August with an average temp of 69°F. January and February are the chilliest months when the average temp is 31°F. The rainiest months are October and July.

Why should I book my Wingdale hotel with Hotels.com?

There are plenty of reasons to book your Wingdale travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.