Chalets in Cheshire
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A lake surrounded by autumn-colored trees and hills.

Search Chalets in Cheshire from CA $470

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

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Our top choices for Cheshire chalets

A red wooden house with multiple windows and a front door, surrounded by trees and a stone pathway.

A cozy room with a large window, a wooden bench, and a sofa.

A wooden staircase leading to a second floor with a large window and a glass door.

A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

1. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Charlemont

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"

Georgia P.

The price is CA $471

CA $471

CA $1,751 total

includes taxes & fees

Nov 16 - Nov 17

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

A large, two-story house with a spacious front yard and a well-maintained lawn.

A spacious dining area with a large table set for six, surrounded by wooden chairs.

A bedroom with a large bed, a chandelier, a window with curtains, and a mirror reflecting a bathroom.

2. Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.

Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.

Cropseyville

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"Wonderful home and property. Stayed for a family wedding weekend. The home, hot tub and pool were a perfect way to relax before and after the ceremony."

Patrick H.

The price is CA $1,162

CA $1,162

CA $2,245 total

includes taxes & fees

Dec 2 - Dec 3

Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.

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

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.

See all hotels in Cheshire

Top reviews in Cheshire

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

Hotel On North

Pittsfield

10/10 Excellent

This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night.

alan

Reviewed October 8, 2026Reviewed October 8, 2026

Hotel On North

A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.

A living room with a sofa, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.

A kitchen with a fireplace, dining area, and a large window with curtains.

Williamstown Motel

Williamstown

10/10 Excellent

A pleasant surprise. The staff was very friendly and even accepted to change my reservation day. The service at the counter was exceptional. The room was clean, nice bathroom, AC. No complaints.

Guy

Reviewed July 16, 2024Reviewed July 16, 2024

Williamstown Motel

A house with a porch, snow-covered ground, and a Christmas tree with lights.

A garden with a swing set, a blue chair, and a flower bed.

A breakfast buffet setup with cereal, milk, juice, and pastries.

A swimming pool with lounge chairs and a fence.

Maple Terrace Motel

Williamstown

10/10 Excellent

The room is clean, well stocked and spacious. Check in was smooth oth and the front desk staff was warm and helpful.

Tanya

Reviewed January 2, 2026Reviewed January 2, 2026

Maple Terrace Motel

A white two-story building with a porch, labeled as a motel.

A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.

A hay bale display with pumpkins and scarecrows.

A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.

Willows Motel Williamstown

Williamstown

10/10 Excellent

The owners are really generous and friendly! The Breakfast is the best I ever had anywhere I have ever been! All sorts of fruits, yogurts, all kinds of spreads, different types of bread, and all organic. Amazing generosity!

Alexander

Reviewed September 20, 2023Reviewed September 20, 2023

Willows Motel Williamstown

A covered porch with benches and potted plants, overlooking a parking area with cars and a view of hills.

A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

A sign with the word "CLARM" on a grassy field with a road and trees in the background.

Cozy Corner Motel

Williamstown

10/10 Excellent

Pour le prix, c'est imbattable. Super service, bon petit déjeuner. Je considère le meilleur motel a ce prix.

alain

Reviewed August 6, 2024Reviewed August 6, 2024

Cozy Corner Motel

A modern hotel building with the name "Hotel Downtown" on the facade.

A room with large windows, a red patterned rug, a wooden table with benches, and shelves with figurines.

An indoor swimming pool with a colorful mural on the wall, a lifeguard station, and clear pool rules posted.

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

it was beautiful, centrally located, perfect getaway

Tara

Reviewed October 9, 2026Reviewed October 9, 2026

Hotel Downstreet, an Ascend Collection Hotel

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

A spacious living room with large windows, a fireplace, and a variety of seating options.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

Vacation Village in the Berkshires

Williamstown

10/10 Excellent

We enjoyed our stay. Aspects of it

Kiril

Reviewed October 25, 2026Reviewed October 25, 2026

Vacation Village in the Berkshires

A motel named 'The Villager Motel' with a 'VACANCY' sign, a picnic table, and a red planter on the lawn.

A park with picnic tables, a playground, and a large coniferous tree.

A kitchen with a countertop, a refrigerator, and a window.

A hotel room with two beds, a nightstand with a lamp, a television, and framed artwork on the wall.

The Villager Motel

Williamstown

10/10 Excellent

Great service, great price.

Nicolas

Reviewed January 5, 2025Reviewed January 5, 2025

The Villager Motel

Two Adirondack chairs facing a river with a forested hill in the background.

A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A restaurant interior with white tables, cushioned booths, and a bar area.

The Yankee Inn

Lenox

10/10 Excellent

Really clean and quiet.. Love!!

Gilles

Reviewed November 1, 2026Reviewed November 1, 2026

The Yankee Inn

A hotel entrance with a covered driveway, a sign for Hampton Inn & Suites by Hilton, and a brick building with multiple windows.

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

A spacious hotel lobby with multiple seating areas, large windows, and a television.

Hampton Inn & Suites Berkshires-Lenox

Lenox

10/10 Excellent

Very modern and attractive hotel. Looks like it was recently updated. Friendly staff. Excellent breakfast buffet with good choices. Rooms were modern, clean, comfortable and functional. Highly recommend this place!

Smadar

Reviewed September 10, 2022Reviewed September 10, 2022

Hampton Inn & Suites Berkshires-Lenox

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A garden with wooden Adirondack chairs and a stone pathway.

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

large suite with kitchen, closer to shops and mountain

Shamila

Reviewed May 22, 2026Reviewed May 22, 2026

Berkshire Mountain Lodge

A covered balcony with a table and two white wire chairs, a bowl of fruit, and a glass of juice.

A modern living room with a sofa, armchair, coffee table, and ottoman. There is a large abstract painting on the wall, a dining table with chairs, and a staircase leading to an upper level.

A garden with a wooden house, a tree, and a person tending to plants.

A hallway with a wooden door, a bench, and a staircase.

The Trail in Adams - Berkshires’ Art Hotel

Adams

10/10 Excellent

Incredible staff, free parking and cute rooms!

Priscilla

Reviewed May 18, 2026Reviewed May 18, 2026

The Trail in Adams - Berkshires’ Art Hotel

A resort with multiple buildings, a parking area, and a mountainous backdrop.

A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

Jiminy Peak Mountain Resort

Hancock

10/10 Excellent

Belle chambre de style condo avec chambre fermée, salon, cuisinette, salle de bain. Télé dans la chambre et de le salon. Tout ce qu'il faut pour faire la cuisine. Lit confortable et tout les équipements était fonctionnel.

Rémi

Reviewed October 6, 2024Reviewed October 6, 2024

Jiminy Peak Mountain Resort

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Excellent

Wonderful reception staff and housekeeping. beautiful very large rooms. will stay here again.

Lorraine

Reviewed July 3, 2021Reviewed July 3, 2021

Best Western Plus Berkshire Hills Inn & Suites

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A modern apartment with a living room, kitchenette, and dining area.

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

A compact living space with a kitchenette, a dining area, and a sofa.

The Central Downtown Inn & Suites

Pittsfield

10/10 Excellent

The place is wonderful, clean, quiet, convenient to everything and can be recommended to a family and small group. The staff is accomodating.

Agnes

Reviewed April 14, 2026Reviewed April 14, 2026

The Central Downtown Inn & Suites

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Search Chalets in Cheshire from CA $470

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Cheshire chalets

1. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

2. Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.

Learn more about Cheshire

Top reviews in Cheshire

Hotel On North

10/10 Excellent

Explore a world of travel with Expedia