Chalets in East Chatham
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A calm lake surrounded by dense evergreen trees and a few deciduous trees with autumn leaves.

Search Chalets in East Chatham from CA $1,007

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Our top choices for East Chatham chalets

An aerial view of a house surrounded by a forest with autumn foliage.

A swimming pool with a deck, surrounded by outdoor furniture and a large house.

A patio with outdoor seating and a fire pit, surrounded by a grassy area and trees.

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

1. Private Lux Chalet w/heated Pool-Hot Tub-Game Rms

Private Lux Chalet w/heated Pool-Hot Tub-Game Rms

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 $1,008

CA $1,008

CA $2,044 total

includes taxes & fees

Dec 2 - Dec 3

Private Lux Chalet w/heated Pool-Hot Tub-Game Rms

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 East Chatham

Tucked between the Berkshires and Catskills, this charming hamlet offers peaceful hiking trails and the scenic Shaker Swamp Conservancy. Visitors can browse local art at the East Chatham Food Company or catch performances at PS21, a converted apple orchard performance space.

See all hotels in East Chatham

Top reviews in East Chatham

A white house with a porch, a brick chimney, and a garden with potted plants.

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

A spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

The property itself is wonderful. Chloe and Sean are delightful hosts. A great breakfast is icing on the cake.

Timothy

Reviewed June 22, 2023Reviewed June 22, 2023

Inn at Silver Maple Farm

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

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.

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

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

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

A bathroom with a bathtub, a sink, and a book. There is a fireplace with a TV mounted above it.

A restaurant interior with a long counter, dining area, and kitchen in the background.

The Yankee Inn

Lenox

10/10 Excellent

Really clean and quiet.. Love!!

Gilles

Reviewed November 1, 2026Reviewed November 1, 2026

The Yankee Inn

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

A room with a brick wall, a black sofa, two leather armchairs, a wooden coffee table with chess pieces, and two framed pictures.

A room with a brick wall, a round wooden table with a lamp, a chair, and a stack of books.

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

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

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

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

An indoor swimming pool with lounge chairs, a diving board, and a window with a view of trees.

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

A reception area with a wooden reception desk, a seating area with sofas, a colorful stained glass window, a mounted television, and various potted plants.

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

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

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 white colonial-style building with a front porch, multiple windows, and hanging flower baskets.

A garden with various shrubs and flowers, a wooden fence, and a vehicle partially visible on the right.

A two-story building with a balcony, a red door, and a staircase leading to the second floor.

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

Chatham Travel Lodge

Old Chatham

10/10 Excellent

Great comfortable stay. Rooms were clean and the bed was comfortable. Only complaint is that the electric car chargers were broken. Wasn't a huge deal, but call ahead if you need them to confirm they are working.

Edward

Reviewed July 30, 2025Reviewed July 30, 2025

Chatham Travel Lodge

A large building with a prominent tower, surrounded by trees and a winding road.

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

A garden with wooden Adirondack chairs and a stone pathway.

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

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 hotel with a covered entrance, stone facade, and arched windows.

A spacious living room with a stone fireplace, large windows, and modern furniture.

A spacious living area with a high ceiling, a staircase with a wooden railing, a large blue patterned rug, and a white sofa.

A spacious hotel lobby with a high ceiling, large windows, a stone accent wall, and a patterned carpet.

Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

10/10 Excellent

Clean room. Plenty of parking. Convenient breakfast

Mateo

Reviewed October 7, 2026Reviewed October 7, 2026

Comfort Inn & Suites East Greenbush - Albany

A multi-story hotel with a clear entrance, a covered waiting area, and a landscaped front yard.

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

An outdoor patio area with wicker furniture, a fire pit, and a covered seating area.

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

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

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

A table set for dining with a view of a lake and chairs outside.

A lakeside deck with a dock, boats, and a gazebo.

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 wooden deck with two chairs and a table, overlooking a lush green landscape and a golf course.

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

A bedroom with a bed, a desk, a chair, a ceiling fan, and a view of the outdoors.

A wooden deck with a staircase leading to a porch, a white door, and hanging flower baskets.

Micosta Leisure Inn

Hudson

10/10 Excellent

What an amazing place! Perfectly cozy room, a beautiful garden and a very friendly cat who greeted us! We had the perfect stay, Steven is very friendly and easy to contact. We absolutely loved our stay and can't wait to come back. We also saw a shooting star!

Jason

Reviewed October 8, 2026Reviewed October 8, 2026

Micosta Leisure Inn

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

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

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

A bedroom with a large bed, a bedside table with a lamp, and a window with curtains.

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

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

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

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Search Chalets in East Chatham from CA $1,007

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for East Chatham chalets

1. Private Lux Chalet w/heated Pool-Hot Tub-Game Rms

Learn more about East Chatham

Top reviews in East Chatham

Inn at Silver Maple Farm

10/10 Excellent

Explore a world of travel with Expedia