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

Hotels in Wingdale

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Where to stay in Wingdale?

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

A two-story house with a wrap-around porch, multiple windows with shutters, and a steeply pitched roof.

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

A staircase with wooden balusters leading to a landing.

1. Station Inn Pawling

Pawling

$140

$159 total

includes taxes & fees

Nov 22 - Nov 23

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

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.

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.

2. Rocky River Inn

New Milford

$149

$171 total

includes taxes & fees

Oct 26 - Oct 27

A park with a picnic table and chairs, surrounded by lush greenery and trees.

A hotel room with a large bed, a window with curtains, a nightstand with a lamp, and a view of the outdoors.

A bathroom with a toilet, sink, and bathtub.

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

3. Maple Leaf Motel

New Milford

$89

$102 total

includes taxes & fees

Nov 1 - Nov 2

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.

4. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

$94

$109 total

includes taxes & fees

Nov 22 - Nov 23

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

5. The Kent Collection - The Firefly Inn

Kent

$319

$366 total

includes taxes & fees

Oct 28 - Oct 29

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 white house with a brick chimney, a white picket fence, and a garden with yellow flowers.

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

6. Homestead Inn

New Milford

$206

$237 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

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

7. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

$101

$116 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A modern interior with a large meeting table, comfortable seating, and a kitchen area.

A lobby with a wooden bench, a reception desk, and a colorful artwork on the wall.

8. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

$79

$92 total

includes taxes & fees

Nov 22 - Nov 23

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

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.

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

9. Hampton Inn & Suites Poughkeepsie

Crown Heights

$98

$113 total

includes taxes & fees

Nov 1 - Nov 2

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

A corner seating area with patterned sofas, a small table, and a lamp. Large windows provide a view of the outdoors.

A hotel lobby with a striped sofa, a reception desk, and a check-in counter.

A spacious living area with a sofa, coffee table, and a view of the outdoors through large windows.

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

Red Oaks Mill

$114

$128 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.

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

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

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

11. Le Chambord at Curry Estate

Hopewell Junction

$209

$236 total

includes taxes & fees

Oct 25 - Oct 26

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 multi-story hotel with a modern design, featuring a covered outdoor seating area and a parking lot.

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

12. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

$98

$113 total

includes taxes & fees

Nov 16 - Nov 17

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

A gym with exercise equipment, a mirror, and a door leading to a room.

A hotel room with two beds, a desk, a chair, a window with curtains, and a wall-mounted lamp.

A hotel lobby with a check-in counter, two armchairs, a small table, and a mirror.

13. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

$72

$82 total

includes taxes & fees

Nov 15 - Nov 16

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

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

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.

14. La Quinta Inn & Suites by Wyndham Danbury

Danbury

$110

$126 total

includes taxes & fees

Nov 1 - Nov 2

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

A garden with various plants and flowers, a white fence, and outdoor furniture.

A hallway with a table, a vase with flowers, a framed picture, and a painting on the wall.

A two-story white house with a front porch, a red door, and a well-maintained lawn.

15. Millbrook Country House Bed & Breakfast

Millbrook

$240

$272 total

includes taxes & fees

Oct 25 - Oct 26

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

A building with a brick facade, a white fence, and a small garden area with a table and chairs.

A cozy living room with a stone fireplace, wooden furniture, and a coffee station.

A pathway leading to a red barn-like structure, surrounded by lush greenery and trees.

16. Heidi's Inn

Brewster

$130

$141 total

includes taxes & fees

Nov 1 - Nov 2

A bar entrance with a sign reading "21 Lake The Bar".

A wedding ceremony setup with white chairs, a central aisle, and a chandelier.

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

A gazebo with a tiled roof and white columns, surrounded by well-maintained lawns and various shrubs.

17. Ethan Allen Hotel

Danbury

$116

$134 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.

A hotel room with a blue wall, a sofa, a bed, a desk, a lamp, a microwave, and a coffee maker.

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.

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

Danbury

$114

$131 total

includes taxes & fees

Nov 22 - Nov 23

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

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

19. Courtyard By Marriott Danbury

Danbury

$111

$128 total

includes taxes & fees

Nov 8 - Nov 9

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.

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

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

20. Quality Inn Poughkeepsie

Arlington

$93

$108 total

includes taxes & fees

Nov 15 - Nov 16

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

Harlem Valley Golf Club

You might want to practice your swing at Harlem Valley Golf Club, a golf course located 0.8 mi (1.2 km) from central Wingdale.

See properties

Leather Hill Preserve

Leather Hill Preserve is 1.1 mi (1.8 km) from central Wingdale, why not stop by during your stay.

See properties

Dover Veterans Memorial Library

Dover Veterans Memorial Library is worth a visit when in central Wingdale.

See properties

Olivet University

If you'd like to get a taste of Wingdale student life, check out Olivet University, located 0.8 mi (1.2 km) from central Wingdale.

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

The Kent Collection - The Firefly Inn

Kent

10/10 Exceptional

Timothy

Rocky River Inn

New Milford

10/10 Exceptional

Zoe

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

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

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

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

Hampton Inn & Suites Poughkeepsie

Crown Heights

10/10 Exceptional

Andrew

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

Danbury

10/10 Exceptional

Robert

Millbrook Country House Bed & Breakfast

Millbrook

10/10 Exceptional

Anonymous traveler

A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

A wooden counter with a wine bottle, glasses, and a sign.

A hotel room with a large bed, two bedside lamps, a chair, a small table, and a rug.

A two-story building with a sign for Cornwall Inn, featuring a front porch and a mailbox.

Cornwall Inn and Lodge

Cornwall Bridge

10/10 Exceptional

Bethny

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

A spacious bar area with a high ceiling and large windows, surrounded by comfortable seating and a rustic wooden ceiling.

A spacious living room with a large window offering a view of greenery and buildings, a high wooden ceiling, and modern furniture.

A kitchen counter with various baked goods displayed on shelves and a wooden stand.

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Hyde Park

10/10 Exceptional

Sheri

Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

10/10 Exceptional

Leslie

Heidi's Inn

Brewster

10/10 Exceptional

dennis

Courtyard By Marriott Danbury

Danbury

10/10 Exceptional

Laura

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.