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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 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.

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

1. Station Inn Pawling

Pawling

$151

$171 total

includes taxes & fees

Nov 2 - Nov 3

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

2. Rocky River Inn

New Milford

$149

$171 total

includes taxes & fees

Oct 4 - Oct 5

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 toilet, sink, and bathtub.

3. Maple Leaf Motel

New Milford

$89

$102 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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.

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

Red Oaks Mill

$105

$118 total

includes taxes & fees

Oct 7 - Oct 8

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

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

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.

5. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

$83

$96 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 swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple windows.

A modern building with a sign reading 'LA QUINTA' and a landscaped area with a tree and flowers.

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

6. La Quinta Inn & Suites by Wyndham Danbury

Danbury

$115

$132 total

includes taxes & fees

Oct 4 - Oct 5

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 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.

7. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

$94

$109 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 two-story white house with a front porch, a red door, and a well-maintained lawn.

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.

8. Millbrook Country House Bed & Breakfast

Millbrook

$240

$272 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

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

9. Le Chambord at Curry Estate

Hopewell Junction

$209

$236 total

includes taxes & fees

Oct 4 - Oct 5

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

An indoor swimming pool with clear water, a lifeguard chair, and a sunlit area with lounge chairs.

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.

10. Hampton Inn & Suites Poughkeepsie

Crown Heights

$98

$113 total

includes taxes & fees

Nov 2 - Nov 3

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

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

11. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

$96

$111 total

includes taxes & fees

Oct 11 - Oct 12

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.

12. The Kent Collection - The Firefly Inn

Kent

$354

$407 total

includes taxes & fees

Oct 5 - Oct 6

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.

13. Heidi's Inn

Brewster

$148

$160 total

includes taxes & fees

Oct 4 - Oct 5

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 nightstand, and a seating area.

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

14. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

$72

$82 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a large bed, two framed pictures on the wall, a desk with a chair, and a small table.

A hotel corridor with a vending machine, a television, a kitchen area, and a tiled floor.

A hotel with a central entrance, a triangular pediment, and a symmetrical facade.

A spacious kitchen with a central island, wooden flooring, and a view of the outdoors.

15. Inn At Arbor Ridge Hotel & Conference Center

Hopewell Junction

$128

$145 total

includes taxes & fees

Nov 1 - Nov 2

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

A room with a desk, a blue sofa, a window with curtains, and a radiator.

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

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

16. Econo Lodge Bethel - Danbury

Bethel

$104

$119 total

includes taxes & fees

Oct 5 - Oct 6

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

A covered patio with a wooden table and chairs, a sofa, and a ceiling fan.

17. Cornwall Inn and Lodge

Cornwall Bridge

$212

$243 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel room with a sofa, armchair, desk, and a large mirror.

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

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

18. Ethan Allen Hotel

Danbury

$116

$134 total

includes taxes & fees

Nov 1 - Nov 2

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

19. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

$114

$132 total

includes taxes & fees

Nov 3 - Nov 4

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

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

A covered porch with white columns and black hanging lanterns.

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

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

The Kent Collection - The Firefly Inn

Kent

10/10 Exceptional

Timothy

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 large glass windows, a covered walkway, and outdoor seating.

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.

The Heartwood

Arlington

10/10 Exceptional

Susan

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

Millbrook Country House Bed & Breakfast

Millbrook

10/10 Exceptional

Anonymous traveler

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

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

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

La Quinta Inn & Suites by Wyndham Danbury

Danbury

10/10 Exceptional

Louis

Heidi's Inn

Brewster

10/10 Exceptional

dennis

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

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

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

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

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

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

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

Courtyard By Marriott Danbury

Danbury

10/10 Exceptional

Laura

The Milestone Inn

Woodbury

10/10 Exceptional

Elin

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.