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Hotels in Wingdale

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Where to stay in Wingdale?

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

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

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.

1. Station Inn Pawling

Pawling

$151

$171 total

includes taxes & fees

Nov 4 - Nov 5

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

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

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

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.

2. Rocky River Inn

New Milford

$149

$171 total

includes taxes & fees

Oct 6 - Oct 7

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

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.

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 sink, toilet, and bathtub.

3. Maple Leaf Motel

New Milford

$89

$102 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.

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.

A reception desk with a digital display, a potted plant, and a sign that reads 'eat. drink. play.'

4. La Quinta Inn & Suites by Wyndham Danbury

Danbury

$115

$132 total

includes taxes & fees

Oct 6 - Oct 7

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

5. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

$105

$122 total

includes taxes & fees

Oct 26 - Oct 27

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

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

6. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

$87

$101 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

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

7. 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 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.

8. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

$98

$113 total

includes taxes & fees

Oct 11 - Oct 12

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

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

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.

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

Red Oaks Mill

$105

$118 total

includes taxes & fees

Oct 19 - Oct 20

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

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

10. Hampton Inn & Suites Poughkeepsie

Crown Heights

$98

$113 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel dining area with wooden tables and chairs, a kitchen counter, a refrigerator, and a television on the wall.

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

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

11. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

$72

$82 total

includes taxes & fees

Nov 2 - Nov 3

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 formal dining table set with plates, cutlery, and wine glasses, surrounded by chairs.

12. Millbrook Country House Bed & Breakfast

Millbrook

$240

$272 total

includes taxes & fees

Oct 8 - Oct 9

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

A hotel reception area with a wooden reception desk, a black and white doormat, and a large window with a view of greenery.

A living room with a beige wall, a glass coffee table, two leather sofas, a small table with a vase of flowers, and a painting of a blue sky and trees.

A motel with multiple rooms, a large parking lot, and a clear blue sky.

13. Econo Lodge Bethel - Danbury

Bethel

$104

$119 total

includes taxes & fees

Oct 7 - Oct 8

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

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

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

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

14. Courtyard By Marriott Danbury

Danbury

$111

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

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.

15. Le Chambord at Curry Estate

Hopewell Junction

$209

$236 total

includes taxes & fees

Oct 6 - Oct 7

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

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.

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

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

Danbury

$131

$151 total

includes taxes & fees

Oct 11 - Oct 12

A spacious hotel lobby with wooden beams, a central seating area, and large windows offering a view.

A courtyard with stone pathways, various shrubs, and a small tree.

A spacious lobby with a stone fireplace, leather sofas, and a wooden ceiling.

A courtyard with outdoor seating, stone walls, and a variety of plants.

17. Heritage Hotel, Golf & Conference Center

Southbury

$93

$125 total

includes taxes & fees

Nov 1 - Nov 2

A Courtyard by Marriott hotel with a modern design, large windows, and a well-maintained lawn.

A reception area with two wooden reception desks, a wall-mounted screen, and a vending machine labeled "market".

A courtyard with outdoor seating, a small tree, and a building with balconies.

A modern hotel lobby with seating areas, a bar, and a staircase.

18. Courtyard by Marriott Poughkeepsie

Poughkeepsie

$110

$124 total

includes taxes & fees

Oct 26 - Oct 27

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

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

19. Heidi's Inn

Brewster

$148

$160 total

includes taxes & fees

Oct 6 - Oct 7

A hotel room with a large bed, two bedside tables with lamps, and a striped wall.

A neatly made bed with white linens, a white bedside table with a lamp, and a telephone.

A Keurig coffee maker with a cup of coffee and several coffee pods on a tray.

A hotel bathroom with a large mirror, a vanity with drawers, a sink, and a towel rack.

20. The Milestone Inn

Woodbury

$107

$123 total

includes taxes & fees

Oct 6 - Oct 7

View all properties

Go beyond your typical stay in Wingdale

Top landmarks in Wingdale

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.

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Dover Veterans Memorial Library

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

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Leather Hill Preserve

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

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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.

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Pawling Nature Reserve

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

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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

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

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

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

The Kent Collection - The Firefly Inn

Kent

10/10 Exceptional

Timothy

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

Rocky River Inn

New Milford

10/10 Exceptional

Zoe

A long dining table set for a meal with chairs, large windows, and a view of a park.

A modern building with a glass facade, a flat roof with solar panels, and a spacious outdoor area with a metal railing.

A modern building with large glass windows, a covered walkway, and outdoor seating.

A modern lobby with a blue sofa, marble coffee table, and a reception desk with a blackboard.

The Heartwood

Arlington

10/10 Exceptional

Susan

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

Danbury

10/10 Exceptional

Robert

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

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

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

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

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.

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

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.

Hampton Inn Danbury

Danbury

10/10 Exceptional

Elizabeth

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

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

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

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

Comfort Suites Fishkill near Interstate 84

Fishkill

10/10 Exceptional

Susan

Millbrook Country House Bed & Breakfast

Millbrook

10/10 Exceptional

Anonymous traveler

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

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

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

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

La Quinta Inn & Suites by Wyndham Danbury

Danbury

10/10 Exceptional

Louis

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 hotel with a covered entrance, multiple windows, and a sign that reads "Gold Award Winner."

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.

Quality Inn & Suites Fishkill South near I-84

Fishkill

10/10 Exceptional

Lynn

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.