Chalets in Sugar Loaf
Chester
New York
United States of America
Chalets
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Search Chalets in Sugar Loaf from CA $383

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your current months are November, 2026 and December, 2026.

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Our top choices for Sugar Loaf chalets

A rustic cabin with a large deck and multiple windows, surrounded by dense forest.

A dining area with a large table, chairs, and a view of greenery through large windows.

A wooden cabin with large windows, a hot tub, and a deck.

A spacious living room with a high ceiling, a green sofa, a black armchair, and a white shag rug.

1. Mountain View Retreat w/ Hot Tub, Theater, and Gym

Mountain View Retreat w/ Hot Tub, Theater, and Gym

Warwick

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Amazing stay on a beautiful place!"

Dorian G.

The price is CA $1,013

CA $1,013

CA $1,960 total

includes taxes & fees

Nov 9 - Nov 10

Mountain View Retreat w/ Hot Tub, Theater, and Gym

A swimming pool surrounded by snow, with people swimming and a building in the background.

A room with a blue sliding barn door, a chandelier, framed artwork, and a potted plant.

A bathroom with white tiled walls, a glass shower enclosure, and a black showerhead.

A fire pit surrounded by six Adirondack chairs in a grassy outdoor area with dense trees in the background.

2. Luxe 10 Guest Ski Chalet · Mountain Creek · Fire Pit · Spa · Golf · Hiking · Ski

Luxe 10 Guest Ski Chalet · Mountain Creek · Fire Pit · Spa · Golf · Hiking · Ski

vernon

9.2 out of 10, Wonderful, (68 reviews)

9.2/10

Wonderful

(68 reviews)

"Theses accommodations were perfect! We had to find accommodation for 10 people attending a close family friends wedding on short notice due to prior accommodation falling through at the last minute! In the end we were glad we had to make the change as this location was perfect go large groups and had great outdoor sitting areas! Would definitely stay again!"

Kirstin V.

The price is CA $384

CA $384

CA $822 total

includes taxes & fees

Nov 9 - Nov 10

Luxe 10 Guest Ski Chalet · Mountain Creek · Fire Pit · Spa · Golf · Hiking · Ski

A log cabin with a patio area featuring outdoor seating and a hot tub.

A spacious cabin with a high ceiling, large windows, a fireplace, and a dining area.

A spacious log cabin interior with a dining area, living room, kitchen, and a stone fireplace.

A bathroom with a glass shower enclosure, wooden walls, a bed with blue bedding, and a large mirror.

3. Ski House - ON THE SLOPE w/ hot tub

Ski House - ON THE SLOPE w/ hot tub

Vernon Township

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

"There for the spartan - great location - house is beautiful - perfect for our group can’t wait to go back again! "

JoeGina M.

The price is CA $992

CA $992

CA $1,343 total

includes taxes & fees

Nov 9 - Nov 10

Ski House - ON THE SLOPE w/ hot tub

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

View all properties

Top reviews in Sugar Loaf

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a well-lit facade.

A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.

A modern hotel lobby with a large map mural, seating areas, and a reception desk.

A Simon Premium Outlet sign at Woodbury Commons.

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

10/10 Excellent

locate in a quiet area but close to a hwy exit. 15 mins drive to Woodbury Common Outlet. There is a CVS, gas station and some food options available. Taco Bell / Burger King next door.

Alex

Reviewed December 24, 2023Reviewed December 24, 2023

Holiday Inn Express Hotel & Suites Chester by IHG

A hotel entrance with stone pillars, a covered walkway, and a bench.

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

A modern hotel room with a flat-screen TV, a fireplace, a desk with a computer, and comfortable seating.

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

Sleep Inn & Suites Monroe - Woodbury

Monroe

10/10 Excellent

Excellent rapport qualité prix. Le meilleur ds le coin. Rien à redire.

Helene

Reviewed July 25, 2024Reviewed July 25, 2024

Sleep Inn & Suites Monroe - Woodbury

A Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.

A modern restaurant with a long counter, wooden chairs, and pendant lighting.

A spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee table.

An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

10/10 Excellent

Be mindful of kids playing with breakfast tools in the breakfast area.

Bahaiddine

Reviewed August 4, 2026Reviewed August 4, 2026

Fairfield Inn & Suites by Marriott Goshen Middletown

La Quinta Inn & Suites by Wyndham Middletown-Goshen

A pool area with a hot tub, a pool lift, and safety signs on the walls.

A hotel lobby with orange seating, a dining area, and a TV screen.

A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

10/10 Excellent

great!

Sumaya

Reviewed September 9, 2026Reviewed September 9, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen

A Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.

A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

A modern lobby with a brown sofa, yellow armchairs, a patterned carpet, and a decorative plant centerpiece.

Sleep Inn & Suites Middletown - Goshen

Middletown

10/10 Excellent

We enjoyed the room, clean, helpful staff. The kids loved the pool and breakfast

Tawnia

Reviewed October 13, 2026Reviewed October 13, 2026

Sleep Inn & Suites Middletown - Goshen

A multi-story hotel with a modern design, featuring a central courtyard, large windows, and a parking lot.

A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.

An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.

A spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.

Residence Inn by Marriott Middletown Goshen

Middletown

10/10 Excellent

Clean and modern

arlene

Reviewed December 1, 2025Reviewed December 1, 2025

Residence Inn by Marriott Middletown Goshen

A Holiday Inn Express & Suites building with a covered entrance, stone facade, and a parking area with a bench.

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

A buffet with various food items, including omelets and baked goods, served in metal trays.

An indoor swimming pool with clear water, a lifebuoy, and a sign indicating no diving allowed.

Holiday Inn Express & Suites Montgomery by IHG

Montgomery

10/10 Excellent

The staff was great! The room was clean and the breakfast was excellent.

Joey

Reviewed January 12, 2026Reviewed January 12, 2026

Holiday Inn Express & Suites Montgomery by IHG

A circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.

A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

A swimming pool with four lounge chairs and a metal ladder.

A modern living room with a sofa, coffee table, and a TV. There is a kitchen area with cabinets and a microwave.

Candlewood Suites Middletown Goshen by IHG

Middletown

8/10 Good

We stayed for 1 night at this hotel and loved it! It’s clean, the beds and pillows are comfy, the room size is good. Large fridge and freezer as well in the room. The only thing missing, in my opinion, is a restaurant for breakfast at the hotel!

Stamatia

Reviewed July 23, 2026Reviewed July 23, 2026

Candlewood Suites Middletown Goshen by IHG

A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.

A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

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

A gym with exercise equipment, treadmills, and weight machines.

Hampton Inn by Hilton Middletown

Middletown

10/10 Excellent

Convenient location for traveling through

Bruce

Reviewed June 11, 2026Reviewed June 11, 2026

Hampton Inn by Hilton Middletown

A multi-story hotel with a prominent entrance, stone pillars, and a well-maintained lawn.

A spacious living area with a curved sofa, a fireplace, and a modern chandelier.

A spacious hotel lobby with a large dining table, comfortable seating, and ceiling fans.

A conference room with a desk, two monitors, a chair, and a blue sofa.

Homewood Suites Stewart Airport

New Windsor

10/10 Excellent

All around great place to stay . We were on our way to NYC. Would strongly recommend. Txs

Anonymous traveller

Reviewed March 13, 2017Reviewed March 13, 2017

Homewood Suites Stewart Airport

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Search Chalets in Sugar Loaf from CA $383

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Sugar Loaf chalets

1. Mountain View Retreat w/ Hot Tub, Theater, and Gym

2. Luxe 10 Guest Ski Chalet · Mountain Creek · Fire Pit · Spa · Golf · Hiking · Ski

3. Ski House - ON THE SLOPE w/ hot tub

Top reviews in Sugar Loaf

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent

Explore a world of travel with Expedia