Chalets in Brainard
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Search Chalets in Brainard from CA $1,162

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

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Our top choices for Brainard chalets

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

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

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.

1. 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

Top reviews in Brainard

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

A wooden interior with a table, chair, and a view of a red barn through an open door.

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

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

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

A spacious living area with a blue sofa, yellow armchair, and a coffee table. A staircase leads to an upper level with a balcony.

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 classic facade, large windows, and a prominent entrance.

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.

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

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

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

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.

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

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

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

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

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

The Yankee Inn

Lenox

10/10 Excellent

Really clean and quiet.. Love!!

Gilles

Reviewed November 1, 2026Reviewed November 1, 2026

The Yankee Inn

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

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 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.

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

A garden with wooden Adirondack chairs and a stone pathway.

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

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

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 modern hotel with a stone facade, a covered entrance, and a clear blue sky.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a tiled deck.

An outdoor seating area with blue sofas and a stone fire pit.

A modern hotel lobby with a dining area, a reception desk, and a bar.

Hampton Inn & Suites Albany-East Greenbush

East Greenbush

10/10 Excellent

Very clean room, well maintained. Nicely renovated / finished. House keeping does a thorough job. Would stay again 10/10

Andrew

Reviewed October 5, 2026Reviewed October 5, 2026

Hampton Inn & Suites Albany-East Greenbush

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

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

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

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

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 hotel with a prominent American flag, a well-lit entrance, and a clear view of the building's exterior.

A living room with a stone fireplace, a flat-screen TV mounted above it, and leather armchairs with plaid upholstery.

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

A hotel room with a sofa, a desk, a flat-screen TV, a bed, and a small table.

Residence Inn by Marriott Albany East Greenbush/Tech Valley

East Greenbush

10/10 Excellent

Ten days on a business trip - really great support from the staff - able to get me great business facilities with very short notice - comfortable too

Anonymous traveller

Reviewed December 20, 2015Reviewed December 20, 2015

Residence Inn by Marriott Albany East Greenbush/Tech Valley

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Search Chalets in Brainard from CA $1,162

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Brainard chalets

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

Top reviews in Brainard

Inn at Silver Maple Farm

10/10 Excellent

Explore a world of travel with Expedia