Chalets in Middlefield
Massachusetts
United States of America
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A snow-covered forest with a stone bridge in the background.

Search Chalets in Middlefield from CA $470

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

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Our top choices for Middlefield chalets

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

A wooden interior with a high ceiling, a stone wall, and a wooden staircase.

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

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

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 Middlefield

Venture to sights like Skyline Trail and Fox Den Wildlife Management Area as you discover Middlefield.

See all hotels in Middlefield

Top reviews in Middlefield

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

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

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

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 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 setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

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

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

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 Super 8 motel with a two-story building, a parking lot, and a picnic table.

Quality Inn Lee - Lenox South

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

Quality Inn Lee - Lenox South

Lee

10/10 Excellent

For a one night on our way to the East coast, it was great. Was surprised how complete the continental breakfast was as the price was so reasonable. Would definitely stay here again.

Dale

Reviewed May 5, 2019Reviewed May 5, 2019

Quality Inn Lee - Lenox South

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

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

A hotel patio with outdoor seating and a fire pit.

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

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

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

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 brick building with a sign reading "The Ellery."

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

A modern hotel room with a bed, sofa, dining table, and chairs.

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

The Ellery

Northampton

10/10 Excellent

We stayed 5 days in the ground floor coach house room which was a lovely, large room with a sitting and dinning area as well as a private patio area. The room was lovely, AC worked great on an extremely hot week and the breakfast, all days snacks and common area were great as well. The staff was helpful with tips about things to do in the area. We had a great visit.

Graham

Reviewed July 5, 2026Reviewed July 5, 2026

The Ellery

A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

A café with a display case, a frozen food section, and a marketplace sign.

A living room with a sofa, armchair, coffee table, and a patterned rug.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

10/10 Excellent

Great well run resort property

Andrea

Reviewed July 1, 2026Reviewed July 1, 2026

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

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 large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

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 snow-covered outdoor area with a patio, seating, and a covered dining area.

A dining area with a glass table, red walls, and framed artwork.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Excellent stay at the Cornell Inn. Very nice property a close walk into town. Well-kept facility and very helpful staff. The Berkshires are beautiful and the Cornell Inn is an excellent choice!

Michael

Reviewed July 6, 2026Reviewed July 6, 2026

The Cornell Inn, Lenox & The Berkshires

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A hotel room with two beds, a desk, a television, and a dresser.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

Excellent room! Clean and good breakfast!

Kelly

Reviewed October 10, 2026Reviewed October 10, 2026

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

A red building with a sign reading "Shaker Mill Inn."

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

Shaker Mill Inn

West Stockbridge

10/10 Excellent

The Shaker Inn is a very unique place. Enjoy our stay .

Richard

Reviewed October 11, 2024Reviewed October 11, 2024

Shaker Mill Inn

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Search Chalets in Middlefield 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 Middlefield chalets

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

Learn more about Middlefield

Top reviews in Middlefield

The Yankee Inn

10/10 Excellent

Explore a world of travel with Expedia