Chalets in Windsor
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Our top choices for Windsor chalets

A view of a forested area with a bench in the foreground.

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

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.

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

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 Windsor

A building entrance with a large planter with purple flowers and a small tree.

A library with bookshelves, a television, and two armchairs.

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

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

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

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

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

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

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

The Yankee Inn

Lenox

10/10 Excellent

Really clean and quiet.. Love!!

Gilles

Reviewed November 1, 2026Reviewed November 1, 2026

The Yankee Inn

A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

A large, single-story building with a red and white exterior, surrounded by green fields and a winding road.

A bedroom with a large bed, a chair, a desk, and a view of the mountains through the window.

A modern building with a flat roof and large windows, surrounded by a pond and trees with autumn foliage.

Blue Vista Motor Lodge

North Adams

10/10 Excellent

Property is beautiful with breathtaking views ! The fire pits , sauna and hot hubs are a great addition to a great motel ! Early sunrise viewing a must ! North Adams is a great town nearby -

patricia

Reviewed September 1, 2025Reviewed September 1, 2025

Blue Vista Motor Lodge

A garden with wooden Adirondack chairs and a stone pathway.

A spacious lobby with a fireplace, seating area, and a bar.

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

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 room with a hanging bed, a white wall, a window, and a door.

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

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

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

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

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

A swimming pool with lounge chairs and a fence.

A garden with a wooden pergola, potted plants, and a lawn with chairs.

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

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

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

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

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

So quiet and very friendly and they went out of there way to make us feel welcome

Pete

Reviewed July 5, 2019Reviewed July 5, 2019

Hilton Garden Inn Lenox Pittsfield

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

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

A hay bale display with pumpkins and scarecrows.

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

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 small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

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

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

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 lodge with a large building and a dock by a lake, surrounded by forest.

A dining area with large windows, wooden furniture, and a view of a lake.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A lakeside dock with kayaks and a covered boat ramp.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Clean rooms and lovely view

Laraib

Reviewed May 21, 2026Reviewed May 21, 2026

The Black Swan Lee - Lenox, an Ascend Collection Hotel

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

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

A spacious living room with a fireplace, comfortable seating, and large windows.

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

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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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Historic 1804 house in N Becket Village in the Berkshires
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Adams Vacations
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Visit Shelburne Falls
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Lenox Library
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Ventfort Hall Mansion and Gilded Age Museum
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Search Chalets in Windsor 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 Windsor chalets

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

Top reviews in Windsor

Hotel On North

10/10 Excellent

Explore a world of travel with Expedia