Top 10 Hotels in Wingdale, NY (from $107) 2026 - Competitive Prices

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Our top choices for Wingdale hotels

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

Fang

$164 nightly

$186 total

Oct 1 - Oct 2

Total with taxes and fees

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 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.

2. Rocky River Inn

New Milford

Nancy

$139 nightly

$160 total

Oct 1 - Oct 2

Total with taxes and fees

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

Corrina

$98 nightly

$113 total

Oct 1 - Oct 2

Total with taxes and fees

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.

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

4. Hampton Inn & Suites Poughkeepsie

Crown Heights

Sanford

$93 nightly

$109 total

Oct 19 - Oct 20

Total with taxes and fees

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

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

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.

5. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

John

$92 nightly

$107 total

Oct 26 - Oct 27

Total with taxes and fees

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

6. La Quinta Inn & Suites by Wyndham Danbury

Danbury

Steven

$115 nightly

$132 total

Oct 4 - Oct 5

Total with taxes and fees

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

7. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

Loze

$107 nightly

$123 total

Oct 11 - Oct 12

Total with taxes and fees

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 covered porch with white columns and black hanging lanterns.

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

8. The Milestone Inn

Woodbury

KEITH

$98 nightly

$112 total

Oct 1 - Oct 2

Total with taxes and fees

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.

9. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

Marco

$118 nightly

$137 total

Oct 7 - Oct 8

Total with taxes and fees

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.

10. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

Ron

$81 nightly

$91 total

Oct 19 - Oct 20

Total with taxes and fees

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

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

11. Heritage Hotel, Golf & Conference Center

Southbury

anthony

$122 nightly

$141 total

Oct 12 - Oct 13

Total with taxes and fees

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.

12. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

Jacqueline Sue

$110 nightly

$128 total

Oct 13 - Oct 14

Total with taxes and fees

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

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

Red Oaks Mill

Aixa

$132 nightly

$149 total

Oct 5 - Oct 6

Total with taxes and fees

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.

14. Heidi's Inn

Brewster

Jill

$148 nightly

$160 total

Oct 1 - Oct 2

Total with taxes and fees

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 modern room with a wooden wardrobe, a white shelf, and a yellow office chair.

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

Danbury

Jay

$127 nightly

$146 total

Oct 4 - Oct 5

Total with taxes and fees

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

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

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.

16. Ethan Allen Hotel

Danbury

David

$111 nightly

$128 total

Oct 25 - Oct 26

Total with taxes and fees

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

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.

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

17. Comfort Suites Fishkill near Interstate 84

Fishkill

Daniel

$111 nightly

$128 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

18. Courtyard by Marriott Poughkeepsie

Poughkeepsie

Celine

$110 nightly

$124 total

Oct 26 - Oct 27

Total with taxes and fees

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

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

An indoor swimming pool with clear pool rules, a lifeguard chair, and a poolside area with lounge chairs.

A hotel corridor with a vending machine, a refrigerator, and a door.

19. Quality Inn Poughkeepsie

Arlington

Dawn

$97 nightly

$113 total

Oct 21 - Oct 22

Total with taxes and fees

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

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

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

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

20. Courtyard By Marriott Danbury

Danbury

Julie

$127 nightly

$146 total

Oct 25 - Oct 26

Total with taxes and fees

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Stay near popular Wingdale attractions

Harlem Valley Golf Club

Enjoy a round of golf in Wingdale at Harlem Valley Golf Club.

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Dover Veterans Memorial Library

After visiting Dover Veterans Memorial Library, make a plan to see the other sights and activities in Wingdale.

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Leather Hill Preserve

You can take time to visit Leather Hill Preserve during your travels to Wingdale.

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Olivet University

Walk around the campus at Olivet University during your stay in Wingdale.

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Pawling Nature Reserve

You can take time to visit Pawling Nature Reserve during your travels to Wingdale.

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Learn more about Wingdale

Head to sights like Dover Veterans Memorial Library and Harlem Valley Golf Club as you discover Wingdale.

See all hotels in Wingdale

A weathered window with a view of trees and a building in the background.

Top Wingdale Hotel Reviews

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent

"Clean room great breakfast"

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent

"Nice hotel. Good quality. Spotless clean"

Holiday Inn Express Poughkeepsie by IHG

8/10 Good

"Nice staff clean space good breakfast"

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

8/10 Good

"The hotel overall is very well kept and clean. Location was perfect and staff was helpful. Would recommend staying here if it’s in your budget or if you’re at the right time of season like we were."

Quality Inn Poughkeepsie

8/10 Good

"The room was decent. Clean and comfortable bed. Quiet. Rusty, leaning floor lamp in corner of bedroom. Decent value. The bathroom was not in great condition. Damaged ceiling tile over the shower from second floor. Empty shampoo conditioner mounted on shower wall. Very sparce continental breakfast."

Ethan Allen Hotel

10/10 Excellent

"Perfect location for us and right near highway."

Studio 6 Extended Stay Fishkill Westage Center NY

8/10 Good

"The building was easy to access, The property needs some updating and TLC but the staff was amazing very friendly and helpful."

Home2 Suites By Hilton Poughkeepsie

8/10 Good

"all good"

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent

"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."

More cheap stays in Wingdale

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY

$92 nightly

$107 total

Oct 26 - Oct 27

Total with taxes and fees

8.6/10 Excellent! (1,000 reviews)

Quality Inn Poughkeepsie

536 Haight Ave, Building A Poughkeepsie NY

$97 nightly

$113 total

Oct 21 - Oct 22

Total with taxes and fees

7.6/10 Good! (595 reviews)

Best Western Danbury/Bethel

11 Stony Hill Road Bethel CT

$100 nightly

$115 total

Oct 11 - Oct 12

Total with taxes and fees

7.8/10 Good! (1,008 reviews)

Microtel Inn & Suites by Wyndham Bethel/Danbury

80 Benedict Rd Bethel CT

$107 nightly

$123 total

Oct 11 - Oct 12

Total with taxes and fees

Comfort Suites Fishkill near Interstate 84

835 Route 52 Fishkill NY

$111 nightly

$128 total

Oct 25 - Oct 26

Total with taxes and fees

Comfort Inn & Suites Danbury-Bethel

80 Newtown Road Danbury CT

$119 nightly

$137 total

Oct 25 - Oct 26

Total with taxes and fees

8.4/10 Very Good! (899 reviews)

Hotels in Wingdale with star-rating

Frequently asked questions

What is the best area to stay in Wingdale?

For visitors to Wingdale, the best area to stay is directly within the resort property itself, as Wingdale is primarily known for this singular, expansive destination.The resort is designed as a self-contained retreat, offering a variety of accommodations, dining options, and recreational activities all within its grounds. You'll find everything from a large, serene lake for water activities to extensive hiking trails winding through the natural landscape. The property also features tennis courts, a golf course, and a large indoor fitness center with high-end equipment and group classes.Couples looking for a relaxing escape will find the resort particularly appealing. The spacious grounds provide ample opportunities for quiet walks, spa treatments, and enjoying meals with scenic views. Many accommodations offer private balconies or patios, enhancing the sense of seclusion and tranquility.For families, the resort offers numerous activities to keep everyone engaged, including a large outdoor pool area and organized recreational programs.

When is the best time to go to Wingdale?

While Wingdale doesn't typically serve as a primary destination, the best times to visit the surrounding Dutchess County area are during the spring, summer, and fall months, from May through October.Late spring and early summer, particularly May and June, offer pleasant weather for outdoor activities. The rolling hills are lush, and local farms begin to open for produce and flower picking. It's an excellent time for couples interested in scenic drives and visiting local vineyards or small towns without the peak summer crowds.For those seeking the warmest weather and a full range of outdoor options, July and August are ideal. This period is superb for families looking to enjoy nearby lakes, hiking trails, and outdoor dining experiences. Many seasonal attractions are fully operational, offering plenty of activities for all ages.The fall, especially September and October, is arguably the most picturesque time to visit due to the stunning foliage. The cooler temperatures make it comfortable for exploring the numerous hiking trails and enjoying the vibrant autumn colors.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Wingdale.

How much is the nightly rate at a Wingdale hotel?

Prices for hotels in Wingdale often vary, but you can find a great deal from $107 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Things to do in Poughkeepsie

Find hotels in Wingdale, NY from $107

Upfront pricing

Treat yourself

Be picky

Go beyond your typical stay in Wingdale

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Wingdale hotels

1. Station Inn Pawling

2. Rocky River Inn

3. Maple Leaf Motel

4. Hampton Inn & Suites Poughkeepsie

5. Holiday Inn Express Poughkeepsie by IHG

6. La Quinta Inn & Suites by Wyndham Danbury

7. Microtel Inn & Suites by Wyndham Bethel/Danbury

8. The Milestone Inn

9. Home2 Suites By Hilton Poughkeepsie

10. Quality Inn Hyde Park Poughkeepsie North

11. Heritage Hotel, Golf & Conference Center

12. Hyatt Place Poughkeepsie / Hudson Valley

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

14. Heidi's Inn

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

16. Ethan Allen Hotel

17. Comfort Suites Fishkill near Interstate 84

18. Courtyard by Marriott Poughkeepsie

19. Quality Inn Poughkeepsie

20. Courtyard By Marriott Danbury

Stay near popular Wingdale attractions

Harlem Valley Golf Club

Dover Veterans Memorial Library

Leather Hill Preserve

Olivet University

Pawling Nature Reserve

Learn more about Wingdale

Top Wingdale Hotel Reviews

Hyatt Place Poughkeepsie / Hudson Valley

Quality Inn Hyde Park Poughkeepsie North

Holiday Inn Express Poughkeepsie by IHG

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Quality Inn Poughkeepsie

Ethan Allen Hotel

Studio 6 Extended Stay Fishkill Westage Center NY

Home2 Suites By Hilton Poughkeepsie

Mayflower Inn & Spa, Auberge Collection

More cheap stays in Wingdale

Holiday Inn Express Poughkeepsie by IHG

Quality Inn Poughkeepsie

Best Western Danbury/Bethel

Microtel Inn & Suites by Wyndham Bethel/Danbury

Comfort Suites Fishkill near Interstate 84

Comfort Inn & Suites Danbury-Bethel

Hotels in Wingdale with star-rating

Frequently asked questions

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