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Hotels in Wingdale

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Where to stay in Wingdale?

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

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.

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.

1. Rocky River Inn

New Milford

$149

$171 total

includes taxes & fees

Oct 4 - Oct 5

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 staircase with wooden balusters leading to a landing.

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

2. Station Inn Pawling

Pawling

$152

$172 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

Red Oaks Mill

$105

$118 total

includes taxes & fees

Oct 6 - Oct 7

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

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

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

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

5. La Quinta Inn & Suites by Wyndham Danbury

Danbury

$115

$132 total

includes taxes & fees

Oct 4 - Oct 5

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

6. 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 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 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 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.

8. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

$96

$111 total

includes taxes & fees

Oct 11 - Oct 12

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

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

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

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

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

10. Ethan Allen Hotel

Danbury

$116

$134 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 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.

11. Millbrook Country House Bed & Breakfast

Millbrook

$240

$272 total

includes taxes & fees

Oct 4 - Oct 5

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.

12. Econo Lodge Bethel - Danbury

Bethel

$104

$119 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 neatly arranged bedroom with a large bed, a bedside table with a lamp, a chair, and a framed picture on the wall.

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.

13. Le Chambord at Curry Estate

Hopewell Junction

$209

$236 total

includes taxes & fees

Oct 4 - Oct 5

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 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.

14. Heidi's Inn

Brewster

$148

$160 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

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

15. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

$118

$137 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

$127

$146 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.

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.

17. Comfort Suites Fishkill near Interstate 84

Fishkill

$98

$113 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

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

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

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

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

19. Courtyard by Marriott Poughkeepsie

Poughkeepsie

$110

$124 total

includes taxes & fees

Oct 26 - Oct 27

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.

20. Courtyard By Marriott Danbury

Danbury

$111

$128 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

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 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

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

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.

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

A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

A hotel room with a bed, a sofa, a small table, a floor lamp, and two windows with curtains.

A spacious foyer with a wooden staircase, a reception desk, and a seating area.

An outdoor patio area with wooden flooring, green metal chairs, and tables under umbrellas.

The Abner Hotel

Litchfield Historic District

10/10 Exceptional

Karen

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 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.

A spacious living area with sofas, a fireplace, and artwork on the walls.

Quality Inn & Suites Fishkill South near I-84

Fishkill

10/10 Exceptional

Lynn

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

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.

A refrigerated display case with various beverages and snacks, and adjacent shelves stocked with packaged goods.

Residence Inn Marriott Danbury

Danbury

10/10 Exceptional

Anonymous traveler

A hotel entrance with a modern design, featuring a prominent sign, stone pillars, and a covered walkway.

A hotel lobby with a checkered floor, seating area, and a reception desk.

A hotel lobby with vending machines, a mini-fridge, and a small refrigerator.

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

Hampton Inn Fishkill

Fishkill

10/10 Exceptional

James

Quality Inn Hyde Park Poughkeepsie North

Hyde Park

10/10 Exceptional

Marjorie

A modern kitchen with dark cabinets, a stainless steel microwave, and a white countertop.

A restaurant with wooden beams, stone pillars, and teal chairs.

A bar area with wooden cabinets, a flat-screen TV, and blue upholstered chairs.

A spacious lobby with a reception desk, seating area, and a chandelier.

HYATT house Fishkill/Poughkeepsie

Fishkill

10/10 Exceptional

Monica

A wooden deck with a swing chair and a bench overlooking a lake.

A modern hotel room with a bed, sofa, leather chair, and a small table.

A tented area with lush greenery and a dining setup.

A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

Interlaken Inn & Resort

Lakeville

10/10 Exceptional

Bruce

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 large bed, a dresser, a chair, and a table. There are three windows with blinds, and a lamp is on a nightstand.

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

The Millerton Inn

Millerton

10/10 Exceptional

Tatiana

A modern bedroom with a large bed, a red sofa, a fireplace, and a television.

A window with a view of a forested area, a small potted plant, and a black kettle on the windowsill.

A room with a long wooden table, multiple chairs, a sofa, and large windows offering a forest view.

A living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

The Harlow House

Rhinebeck

10/10 Exceptional

The Harlow House is a unique, modern hotel. The room was clean, beautiful, and thoughtfully designed. We really enjoyed the king bed and spacious bathroom. Air conditioning worked great and kept us comfortable. Check in was easy. The owner was attentive and quick to respond. The hotel is stunning, situated in the middle of the woods on a quiet, and well kept plot of land. We awoke to a serene setting featuring a family of deer grazing in the nearby woods. It’s only a few minutes drive to...

Matthew

A vintage black car parked on a road with a white fence and trees in the background.

A dining area with wooden chairs and tables, a central wooden display cabinet with glass doors, and a green-lit wall lamp.

A living room with a fireplace, a sofa, a chair, and a coffee table.

A bedroom with two single beds, a nightstand with a lamp, a wooden chair, a door, and a wall-mounted light fixture.

Jenny's Country Manor

Red Hook

10/10 Exceptional

Elyssamay

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

A spacious living room with a large sofa, a round ottoman, and a coffee table. There are shelves with decorative items and a bed with a tufted headboard.

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

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

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.