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

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

1. Station Inn Pawling

Pawling

$150

$169 total

includes taxes & fees

Nov 2 - Nov 3

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

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 5 - Oct 6

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

A bathroom with a sink, toilet, and bathtub.

A bathroom with a toilet, sink, and bathtub.

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

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 5 - Oct 6

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.

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

Two HP desktop computers on a desk with a lamp, keyboard, and mouse.

5. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

$83

$96 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 reception area with a geometric patterned wall, a reception desk, a sofa, and a dining area with chairs and a table.

6. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

$94

$109 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

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

Red Oaks Mill

$105

$118 total

includes taxes & fees

Oct 19 - Oct 20

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

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

A spacious foyer with a wooden ceiling, a large chandelier, a fireplace, and a traditional wooden dresser with drawers.

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.

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

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

A modern hotel room with a dining area, a TV, and a large window with curtains.

9. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

$98

$113 total

includes taxes & fees

Oct 11 - Oct 12

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

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.

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

10. Millbrook Country House Bed & Breakfast

Millbrook

$240

$272 total

includes taxes & fees

Oct 8 - Oct 9

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.

11. Hampton Inn & Suites Poughkeepsie

Crown Heights

$98

$113 total

includes taxes & fees

Nov 2 - Nov 3

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 hotel room with two beds, a nightstand, and a seating area.

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

12. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

$72

$82 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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.

13. Ethan Allen Hotel

Danbury

$116

$134 total

includes taxes & fees

Nov 1 - Nov 2

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.

14. The Milestone Inn

Woodbury

$107

$123 total

includes taxes & fees

Oct 6 - Oct 7

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

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

15. Courtyard By Marriott Danbury

Danbury

$111

$128 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 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.

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

16. Econo Lodge Bethel - Danbury

Bethel

$104

$119 total

includes taxes & fees

Oct 6 - Oct 7

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

17. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

$114

$132 total

includes taxes & fees

Nov 4 - Nov 5

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

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

A spacious hall with round tables and chairs, wooden beams on the ceiling, and large windows allowing natural light.

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

18. Heritage Hotel, Golf & Conference Center

Southbury

$93

$125 total

includes taxes & fees

Nov 1 - Nov 2

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.

19. Heidi's Inn

Brewster

$148

$160 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 hotel room with a large bed, two bedside lamps, a chair, a small table, and a rug.

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

20. Cornwall Inn and Lodge

Cornwall Bridge

$212

$243 total

includes taxes & fees

Nov 1 - Nov 2

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.

See properties

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.

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

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

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

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

The Kent Collection - The Firefly Inn

Kent

10/10 Exceptional

Timothy

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

The Heartwood

Arlington

10/10 Exceptional

Susan

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

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

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

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

Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

10/10 Exceptional

Leslie

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a large window with a forest view.

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.

A snack display with various chips and snacks, a refrigerated beverage area, and framed pictures on the wall.

Hampton Inn Danbury

Danbury

10/10 Exceptional

Elizabeth

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

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

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

A modern hotel room with a sofa, armchair, ottoman, flat-screen TV, and large windows with sheer curtains.

Courtyard by Marriott Poughkeepsie

Poughkeepsie

10/10 Exceptional

Catherine

A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

A room with two yellow armchairs, a small table with a lamp, a framed painting on the wall, and a window with curtains.

A staircase with a wooden handrail and a wall with three framed paintings of forest scenes.

A neatly made bed with white and brown pillows, two bedside lamps, and framed pictures on the wall.

Inn at Pine Plains

Pine Plains

10/10 Exceptional

Kevin

Ethan Allen Hotel

Danbury

10/10 Exceptional

Michael

A multi-story hotel with a brick facade and a large glass entrance.

A hotel lobby with a television, seating area, and large windows.

A hotel lobby with a coffee station, seating area, and a TV screen.

A hotel room with a sofa, a desk with a computer, a television, a bed, and a small table.

Residence Inn Marriott Danbury

Danbury

10/10 Exceptional

Anonymous traveler

A modern kitchen with a dining area, a large window, and a view of the garden.

A white building with a number '9' sign, a covered entrance, and six planters with shrubs.

A modern kitchen with a dining area, a sofa, and a TV mounted on the wall.

A modern outdoor dining area with a round table and white chairs, surrounded by lush greenery and a white railing.

9 Academy

Salisbury

10/10 Exceptional

Louise

A modern bar area with a long counter, multiple bar stools, and a variety of liquor bottles.

A modern restaurant with a long counter, multiple seating areas, and a visible kitchen in the background.

An outdoor patio with wicker furniture, a fire pit, and a view of a brick building and trees.

Holiday Inn Poughkeepsie by IHG

Poughkeepsie

10/10 Exceptional

Gregory

A modern lobby with a high ceiling, brick walls, and a glass enclosure. There are seating areas with tables and chairs, and a kitchen area in the background.

A hotel room with a large bed, a desk with a computer, a television, and a window with curtains.

A room with a blue textured wall, two computer monitors, a desk, two chairs, and a small plant.

A hotel with a modern design, featuring a prominent 'Best Western' sign, large windows, and a well-lit entrance.

Best Western Danbury/Bethel

Bethel

10/10 Exceptional

Mark

An outdoor patio with a fire pit, seating, and umbrellas.

A long dining table set with multiple wine glasses, water glasses, and folded white napkins.

A bedroom with a bed, a sofa, a wooden bench, a window, and a door.

A two-story building with a balcony, outdoor seating area with umbrellas, and potted plants.

The Millerton Inn

Millerton

10/10 Exceptional

Tatiana

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

A hotel reception area with a wooden reception desk, a clock on the wall, and a coffee machine in the background.

A room with a dark blue wall, a round wooden table with a plant, and four patterned chairs.

A modern dining area with wooden tables and chairs, a kitchen area with appliances, and a large wall mural.

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Highland

10/10 Exceptional

Luis

A serene garden with a pond, lush greenery, and a house in the background.

A spacious dining area with wooden tables and chairs, large windows, and ceiling fans.

A bedroom with a large bed, a desk with a lamp, a TV, and a fireplace.

A house with a covered porch, a stone staircase, and a garden with blooming pink flowers.

Buttermilk Falls Inn

Milton

10/10 Exceptional

Amy

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.