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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 staircase with wooden balusters leading to a landing.

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.

1. Station Inn Pawling

Pawling

$137

$155 total

includes taxes & fees

Nov 15 - Nov 16

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 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.

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 bathroom with a sink, toilet, 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.

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

3. Maple Leaf Motel

New Milford

$89

$102 total

includes taxes & fees

Nov 1 - Nov 2

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

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

4. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

$79

$92 total

includes taxes & fees

Nov 15 - Nov 16

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 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.

5. Homestead Inn

New Milford

$206

$237 total

includes taxes & fees

Nov 1 - Nov 2

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

6. The Kent Collection - The Firefly Inn

Kent

$319

$366 total

includes taxes & fees

Oct 26 - Oct 27

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

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

A conference room with multiple tables and chairs, a ceiling light fixture, and a door with an exit sign.

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

7. La Quinta Inn & Suites by Wyndham Danbury

Danbury

$111

$128 total

includes taxes & fees

Oct 18 - Oct 19

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 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.

8. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

$96

$111 total

includes taxes & fees

Nov 15 - Nov 16

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

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

A hotel entrance with a covered walkway, large windows, and a clear sign indicating a 10-foot clearance.

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

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

Red Oaks Mill

$119

$135 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 snack display area with shelves stocked with various snacks and a large wall advertisement for treats.

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.

10. Hampton Inn & Suites Poughkeepsie

Crown Heights

$98

$113 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 formal dining table set with plates, cutlery, and wine glasses, surrounded by chairs.

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

11. Millbrook Country House Bed & Breakfast

Millbrook

$240

$272 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

12. Le Chambord at Curry Estate

Hopewell Junction

$209

$236 total

includes taxes & fees

Oct 18 - Oct 19

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

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

13. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

$101

$116 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

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

Danbury

$118

$136 total

includes taxes & fees

Nov 15 - Nov 16

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.

15. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

$72

$82 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.

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

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

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

16. Heidi's Inn

Brewster

$148

$160 total

includes taxes & fees

Oct 18 - Oct 19

A self-service kiosk with refrigerated and non-refrigerated food items, a coffee machine, and a payment terminal.

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

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

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

17. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

$114

$132 total

includes taxes & fees

Nov 9 - Nov 10

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

18. Courtyard By Marriott Danbury

Danbury

$111

$128 total

includes taxes & fees

Nov 1 - Nov 2

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.

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.

19. Comfort Suites Fishkill near Interstate 84

Fishkill

$98

$113 total

includes taxes & fees

Nov 15 - Nov 16

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

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.

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

20. Quality Inn Poughkeepsie

Arlington

$93

$108 total

includes taxes & fees

Nov 8 - Nov 9

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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.

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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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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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Dover Veterans Memorial Library

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

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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.

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

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

A modern lounge area with seating, tables, and a large vase.

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

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

The Heartwood

Arlington

10/10 Exceptional

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

Hampton Inn & Suites Poughkeepsie

Crown Heights

10/10 Exceptional

Tony

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

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

Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

10/10 Exceptional

Leslie

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

La Quinta Inn & Suites by Wyndham Danbury

Danbury

10/10 Exceptional

Louis

Comfort Suites Fishkill near Interstate 84

Fishkill

10/10 Exceptional

Ashley

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 living area with stone pillars, leather sofas, a fireplace, and a kitchen in the background.

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

Heidi's Inn

Brewster

10/10 Exceptional

dennis

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.