Top 10 Hotels in Wingdale, NY (from $100) 2026 - Competitive Prices

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Our top choices for Wingdale hotels

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 two-story motel with a central patio and a parking lot.

1. Rocky River Inn

New Milford

michael

$114 nightly

$131 total

Sep 30 - Oct 1

Total with taxes and fees

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 staircase with wooden balusters leading to a landing.

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

2. Station Inn Pawling

Pawling

Vienna Hiu Yan

$151 nightly

$171 total

Aug 31 - Sep 1

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, a window with curtains, a nightstand with a lamp, and a view of the outdoors.

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 sink, toilet, and bathtub.

3. Maple Leaf Motel

New Milford

Corrina

$89 nightly

$102 total

Sep 13 - Sep 14

Total with taxes and fees

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

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.

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

4. Homestead Inn

New Milford

gerard

$206 nightly

$237 total

Sep 9 - Sep 10

Total with taxes and fees

A sign for La Grange Inn, a building with a brick facade and a white roof, located at a roadside intersection.

A building with a parking lot, a covered area, and a few cars parked.

A hotel room with two single beds, a small round table, and a lamp.

5. The Lagrange Inn & Extended Stay

Pleasant Valley

Anastasiya

$142 nightly

$160 total

Aug 31 - Sep 1

Total with taxes and fees

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.

6. The Kent Collection - The Firefly Inn

Kent

Candice Burrows

$276 nightly

$318 total

Sep 18 - Sep 19

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

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

A Holiday Inn Express Suites hotel with a central courtyard and a large tree.

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

Danbury

Deborah

$118 nightly

$136 total

Sep 13 - Sep 14

Total with taxes and fees

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 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.

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

Red Oaks Mill

Jacqueline

$124 nightly

$141 total

Sep 24 - Sep 25

Total with taxes and fees

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

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

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

A gazebo with a white porch and a lawn party setup with rows of chairs.

9. Le Chambord at Curry Estate

Hopewell Junction

Melissa

$209 nightly

$236 total

Aug 31 - Sep 1

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 modern bar area with round tables and chairs, a bar counter with a variety of bottles, and a large screen mounted on the wall.

10. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

Katlin

$101 nightly

$117 total

Sep 8 - Sep 9

Total with taxes and fees

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.

11. Heidi's Inn

Brewster

Fan

$148 nightly

$160 total

Aug 31 - Sep 1

Total with taxes and fees

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

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.

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

12. Courtyard By Marriott Danbury

Danbury

Kimberly

$111 nightly

$128 total

Sep 20 - Sep 21

Total with taxes and fees

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 restaurant with brick walls, large windows, and wooden tables and chairs.

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

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

13. Best Western Danbury/Bethel

Bethel

MARYELLEN

$106 nightly

$121 total

Sep 14 - Sep 15

Total with taxes and fees

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

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

14. Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

Jamie

$104 nightly

$120 total

Sep 29 - Sep 30

Total with taxes and fees

A busy bar area with multiple screens displaying content, wooden decor, and a crowd of people.

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

A bar area with multiple VANS branded signs, wooden bar counter, and several bar stools.

A modern building with a sign reading 'LAQUINTA' and a landscaped area with a small tree.

15. La Quinta Inn & Suites by Wyndham Danbury

Danbury

Samantha

$115 nightly

$132 total

Sep 20 - Sep 21

Total with taxes and fees

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

JEANCARLOS

$100 nightly

$115 total

Sep 1 - Sep 2

Total with taxes and fees

A bedroom with two beds, a desk, a chair, a window with curtains, and a door with a glass panel.

A bathroom with a large mirror, a lighted frame, and a door.

A room with a mounted television, a chair, and a coat rack.

A motel sign with a 'VACANCY' notice, surrounded by well-maintained landscaping and a building with a red roof.

17. Hitching Post Country Motel

Cornwall Bridge

Chris

$130 nightly

$150 total

Aug 31 - Sep 1

Total with taxes and fees

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

18. Millbrook Country House Bed & Breakfast

Millbrook

Beth

$240 nightly

$272 total

Sep 3 - Sep 4

Total with taxes and fees

A reception area with two counters, a clock on the wall, and a flower arrangement.

A multi-story building with a stone facade and a brick-paved entrance area.

A hotel lobby with blue sofas, a brown ottoman, a flat-screen TV, and a large window.

A hotel room with a wooden desk, a television, a coffee maker, a lamp, a chair, and a wardrobe.

19. Comfort Inn Brewster

Brewster

ANNA

$140 nightly

$151 total

Sep 27 - Sep 28

Total with taxes and fees

A large, modern hotel with a covered entrance, well-maintained lawns, and a clear sky.

A spacious lobby with a central reception desk, seating areas, and a vending machine.

A fire pit with seating, a covered patio, and a building with large windows.

A Hilton Garden Inn sign with the words "ENTRANCE" below it, surrounded by well-maintained hedges and colorful flower beds.

20. Hilton Garden Inn Danbury

Danbury

Kathryn

$127 nightly

$146 total

Sep 13 - Sep 14

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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Pawling Nature Reserve

You can take time to visit Pawling Nature Reserve during your travels to 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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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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Olivet University

Walk around the campus at Olivet University during your stay in 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

Top Wingdale Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"Facilities were clean but worn down. Our room had a weird smell to it like stale smoke but it’s a no smoking property. Pictures online are much better than the rooms are in person. Inside our room had worn carpet and a broken chair. We could hear the people above us walking in their room all night. Thin walls. If you’re looking for a place to just sleep and go, this would be okay. Not a comfortable place if you want to hang out in your room for the evening. I’m surprised in hotel.com it’s rated and 8-very good. Definitely a solid 7-good rating. Staff was pleasant and breakfast was very good. Overall it was the room I’d rate lower than everything else."

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent

"The lady at the front desk was so friendly and helpful. The property is clean, the rooms were huge. I would definitely stay again"

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Hotel was clean and rooms are very comfortable. Staff was friendly and helpful. Only criticism was that room was not serviced until we called to have towels changed. Also, found it sort of odd that hotel automatically added on a daily parking fee."

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

8/10 Good

"Breakfast was ok. The elevator was broken and we were on the 4th floor. It was fixed in the morning though."

Comfort Inn & Suites Danbury-Bethel

8/10 Good

"Very convenient location but our room location was much quieter on our first stay. Perhaps the hotel was more fully booked, but our first room was much more private."

Holiday Inn Express Poughkeepsie by IHG

8/10 Good

"Rooms were clean and the beds were comfy. Even though the hotel seemed busy, didn’t hear a lot of commotion once inside the room. The rooms were in need of some renovations and could def use a refresh, but completely livable. The bathroom was much smaller than expected. Really disliked that when taking a shower, large amounts of water gushed from the faucet and not out of the shower head (such a waste of water!). Even so, there was plenty of water coming out of the shower head itself. Also, the water never got hot from the sink - the best I could do was a luke warm to wash my face even after running the water for several mins. The breakfast buffet was a welcome meal in the morning. It was hot and well stocked with limited options that were tasty. They have two, single cup, coffee machines that grind a fresh cup every time and are avail for use all day. You may have to wait a min to brew a cup, but worth the extra time."

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent

"Nice staff, quick checking in & out, clean room, good location, restaurant had good food."

Ethan Allen Hotel

8/10 Good

"It's a nice old hotel that could use a major make over. The price was reasonable around $150.00 staff was great although the front desk didn't help us with our receipt for incidentals which was strange. The bar is nice and the breakfast buffet was good enough for $14.00 person. All and all I would book again."

La Quinta Inn & Suites by Wyndham Danbury

10/10 Excellent

"We stop at LaQuina as it is an easy commute to Bridgewater, C"

More cheap stays in Wingdale

SureStay Plus Hotel by Best Western Highland Poughkeepsie

3423 US Highway 9W Highland NY

$89 nightly

$100 total

Sep 7 - Sep 8

Total with taxes and fees

8/10 Very Good! (1,001 reviews)

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY

$98 nightly

$114 total

Sep 28 - Sep 29

Total with taxes and fees

8.8/10 Excellent! (1,006 reviews)

Microtel Inn & Suites by Wyndham Bethel/Danbury

80 Benedict Rd Bethel CT

$104 nightly

$120 total

Sep 29 - Sep 30

Total with taxes and fees

8.2/10 Very Good! (1,002 reviews)

Hampton Inn & Suites Poughkeepsie

2361 South Rd Poughkeepsie NY

$114 nightly

$132 total

Sep 7 - Sep 8

Total with taxes and fees

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

89 Mill Plain Road Danbury CT

$118 nightly

$136 total

Sep 13 - Sep 14

Total with taxes and fees

9.2/10 Wonderful! (444 reviews)

Comfort Inn & Suites Danbury-Bethel

80 Newtown Road Danbury CT

$119 nightly

$137 total

Sep 20 - Sep 21

Total with taxes and fees

8.4/10 Very Good! (842 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 $100 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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Lodging

Find hotels in Wingdale, NY from $100

Upfront pricing

Treat yourself

Be picky

Go beyond your typical stay in Wingdale

Check prices for these dates

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Star rating

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Our top choices for Wingdale hotels

1. Rocky River Inn

2. Station Inn Pawling

3. Maple Leaf Motel

4. Homestead Inn

5. The Lagrange Inn & Extended Stay

6. The Kent Collection - The Firefly Inn

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

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

9. Le Chambord at Curry Estate

10. Hyatt Place Poughkeepsie / Hudson Valley

11. Heidi's Inn

12. Courtyard By Marriott Danbury

13. Best Western Danbury/Bethel

14. Microtel Inn & Suites by Wyndham Bethel/Danbury

15. La Quinta Inn & Suites by Wyndham Danbury

16. Econo Lodge Bethel - Danbury

17. Hitching Post Country Motel

18. Millbrook Country House Bed & Breakfast

19. Comfort Inn Brewster

20. Hilton Garden Inn Danbury

Stay near popular Wingdale attractions

Harlem Valley Golf Club

Pawling Nature Reserve

Leather Hill Preserve

Dover Veterans Memorial Library

Olivet University

Learn more about Wingdale

Top Wingdale Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

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

Comfort Inn & Suites Danbury-Bethel

Holiday Inn Express Poughkeepsie by IHG

DoubleTree by Hilton Poughkeepsie Convention Center

Ethan Allen Hotel

La Quinta Inn & Suites by Wyndham Danbury

More cheap stays in Wingdale

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Holiday Inn Express Poughkeepsie by IHG

Microtel Inn & Suites by Wyndham Bethel/Danbury

Hampton Inn & Suites Poughkeepsie

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

Comfort Inn & Suites Danbury-Bethel

Hotels in Wingdale with star-rating

Frequently asked questions

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