Country Houses in Chatham
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A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Country Houses Chatham CA $189

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

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Our top choices for Chatham country houses

A living room with a fireplace, a television, a sofa, and a dining area.

A cozy dining area with a round table, chairs, and a candle centerpiece. Large windows offer views of a forested landscape.

A kitchen with a window, a table with chairs, a microwave, a kettle, and shelves with various items.

A brick house with a wooden deck, a tree in front, and a trash can.

1. Magic Forest Farm's Artist Retreat

Magic Forest Farm's Artist Retreat

Coeymans Hollow

9.6 out of 10, Exceptional, (8 reviews)

9.6/10

Exceptional

(8 reviews)

"Quaint, but spacious!Tidy, cleanWonderful stay"

J H.

The price is CA $190

CA $190

CA $223 total

includes taxes & fees

Nov 9 - Nov 10

Magic Forest Farm's Artist Retreat

A modern kitchen with white cabinetry, a wooden table, and a large window providing a view of the outdoors.

A spacious living area with a brick fireplace, a dining table with chairs, and a view of the outdoors.

A backyard with a hot tub, outdoor seating, and a patio area.

A spacious living area with a wooden ceiling, a brick fireplace, and a kitchen in the background.

2. Charming 6 Bdrm Countryside Stay

Charming 6 Bdrm Countryside Stay

3.0 star property

Great Barrington

The price is CA $651

CA $651

CA $1,426 total

includes taxes & fees

Nov 30 - Dec 1

Charming 6 Bdrm Countryside Stay

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 Chatham

This charming upstate village hosts the Mac-Haydn Theatre's summer productions and a vibrant Main Street with independent shops and cafés. Explore the historic Union Station or time your visit for the Columbia County Fair, a beloved local tradition since 1841.

See all hotels in Chatham

Top reviews in Chatham

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.

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

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 wooden deck with white railings and hanging flower baskets.

A building with a balcony covered in pink flowers, a paved driveway, and a car parked in the background.

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

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

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

A wooden deck with a staircase leading to a covered porch.

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

A cozy living room with a gray sofa, wooden ceiling beams, a black TV stand, and a dining area with a table and chairs.

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 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 room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.

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 modern kitchen with a built-in oven, microwave, and stainless steel range hood.

A modern interior with a round mirror reflecting a dining area, a large vase, and a guitar.

A hallway with a staircase, a framed painting, a mirror, and a potted plant.

A two-story building with a brick facade and a flat roof.

Howard Hotel

Hudson

10/10 Excellent

Loved how we felt like we were walking into our own place instead of just another hotel. The room was so nice, large, clean, bright. I’ve already recommended it to others.

Alexandra

Reviewed August 6, 2026Reviewed August 6, 2026

Howard Hotel

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

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

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

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

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 kitchen with a stainless steel sink, a window with a view of a wooden deck and yellow chairs, and a door leading to an outdoor area.

A black rocking chair in front of a house with a sign that reads "The Nest" and a small potted plant beside the door.

A bedroom with a large bed, a desk with a mirror, a television on the wall, and a chandelier.

A hallway with a bed in the background, a door with the number 4, and a small table with water bottles and a coffee maker.

The Nest Hudson

Hudson

10/10 Excellent

Great stay! Great location!

Amanda

Reviewed January 1, 2026Reviewed January 1, 2026

The Nest Hudson

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

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

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

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

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

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

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 hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

Monument Mountain Motel

Great Barrington

10/10 Excellent

Perfect motel for an overnight stay. The room and bathroom were fresh and clean. The man and woman staff were friendly and polite.

Paul

Reviewed October 5, 2025Reviewed October 5, 2025

Monument Mountain Motel

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

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

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

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

A bedroom with a bed, bedside table, and a wall-mounted mirror.

A building with a sign reading "NAUTICAL NEST" and a lantern above it.

An outdoor patio with a wooden table and four black wire chairs, surrounded by stone tiles and greenery.

A staircase with white steps and black non-slip treads, leading to a landing with a dark wall and a window with colorful stained glass.

Nautical Nest

Hudson

10/10 Excellent

Roomy and clean and well located - ample legal street parking on union avenue

Aaron Harold

Reviewed June 6, 2026Reviewed June 6, 2026

Nautical Nest

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Country Houses Chatham CA $189

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chatham country houses

1. Magic Forest Farm's Artist Retreat

2. Charming 6 Bdrm Countryside Stay

Learn more about Chatham

Top reviews in Chatham

Inn at Silver Maple Farm

10/10 Excellent

Explore a world of travel with Expedia