Chatham Holiday Rentals, New York: Private House Rentals

A city street with buildings, parked cars, and solar panels.

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Our top choices for Chatham hotels

A wooden deck with white railings and hanging flower baskets.

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

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

A bathroom with a bathtub, toilet, and sink. There is a shower curtain, a towel rack, and a hairdryer.

1. Chatham Travel Lodge

Old Chatham

andrew

2.904.745 ₫

3.253.003 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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

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.

2. Inn at Silver Maple Farm

East Chatham

Erdem

6.336.680 ₫

7.097.082 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

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

3. The Yankee Inn

Lenox

William

2.804.760 ₫

3.133.021 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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

A modern lobby with a reception desk, seating area, and a TV screen.

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a landscaped front yard.

A restaurant with booths and tables, a TV screen, and a counter with a clock.

4. Holiday Inn Express Hotel & Suites West Coxsackie by IHG

West Coxsackie

Glenn

3.064.932 ₫

3.310.127 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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 corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

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

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Bruce

5.055.061 ₫

5.646.504 ₫ total

includes taxes & fees

6 Oct - 7 Oct

6. Berkshire Travel Lodge

Austerlitz

Kris

1.752.715 ₫

1.963.072 ₫ total

includes taxes & fees

30 Sept - 1 Oct

A spacious interior with a high ceiling, exposed brick walls, large windows, and modern furniture.

A modern interior with a brick fireplace, comfortable seating, and large windows offering views of the outdoors.

A modern building with large glass windows and a flat roof.

7. voco James Newbury Hudson Valley by IHG

Coxsackie

Lisa

4.233.110 ₫

4.741.085 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A covered outdoor area with stone pillars and a view of a road and green hills.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

8. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

3.672.418 ₫

4.102.091 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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.

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

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

9. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

2.747.107 ₫

3.068.519 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

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

10. Micosta Leisure Inn

Hudson

Kim

2.563.499 ₫

2.871.244 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

A covered porch with wicker furniture and hanging flower baskets.

11. The Red Lion Inn

Stockbridge

Stephan

4.616.427 ₫

6.446.739 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

A cozy library with bookshelves, a fireplace, and comfortable seating.

12. Berkshires Untold

Lenox

Drue

4.064.098 ₫

4.539.598 ₫ total

includes taxes & fees

30 Sept - 1 Oct

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A Quality Inn sign, a brick building, and a parking lot with cars.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

13. Quality Inn Great Barrington

Great Barrington

Joan

2.626.866 ₫

2.934.209 ₫ total

includes taxes & fees

20 Oct - 21 Oct

An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.

A restaurant with long tables, chairs, and a brick wall.

A spacious bedroom with a large bed, a wooden headboard, a bedside table with a book and a glass, and a window with curtains.

A bar area with wooden beams, a bar counter, and stools.

14. Pocketbook Hotel and Bath

Hudson

Elizabeth

4.927.585 ₫

6.742.016 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A modern hotel lobby with seating areas, tables, and a reception desk.

A breakfast area with a counter, coffee machine, and a display of pastries.

A kitchenette with a microwave, coffee maker, and coffee cups.

A coffee station with two coffee machines and a variety of coffee pods and cups.

15. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Maria Dulce

3.090.430 ₫

3.451.932 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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.

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.

16. Shaker Mill Inn

West Stockbridge

Mervin

4.649.346 ₫

5.100.332 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

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

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

17. Berkshire Mountain Lodge

Pittsfield

Jay

2.067.194 ₫

2.889.226 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A modern dining area with wooden tables and benches, green chairs, and pendant lighting.

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

A vending area with snacks, drinks, and microwaves.

A hotel lobby with orange rocking chairs, a reception desk, and a green carpet.

18. Spark by Hilton West Coxsackie

West Coxsackie

Christian

2.774.543 ₫

2.996.507 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

A wooden wall with a white pendant light fixture.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

19. Prospect Berkshires

Egremont

Conor

8.531.145 ₫

10.399.543 ₫ total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

20. Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

Abram J

3.068.356 ₫

3.405.874 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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Stay near popular Chatham attractions

The Mac-Haydn Theatre

This intimate theater-in-the-round presents professional summer musicals with New York City talent. Every seat offers an immersive view of the dynamic performances, running from Memorial Day through Labour Day.

See 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

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

Top Chatham Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

8/10 Good

"Overall, the cabin was nice. Especially if you're only planning on staying a few days. But for the price you pay for 2 nights, they could have better utensils, pan, a few more cooking utensils and a kettle for the hot water. These are just a few inexpensive amenities that these places should all have! Because most people are probably cooking there own food nowadays either by choice or the fact that there's nothing close by. But aside from the kitchen issues, this was a very nice, enjoyable getaway. I would definitely recommend it to anyone who loves the outdoors!"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Wonderful resort"

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Easy check in. Bright atmosphere. Very helpful and courteous front desk staff."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"This was a nice clean convenient hidden gem. Situated on the water, a little cool right now , but the beginning of fall follege was very pretty. Staff was polite and helpful. I would return."

Quality Inn Great Barrington

10/10 Excellent

"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."

The Red Lion Inn

10/10 Excellent

"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."

The Yankee Inn

10/10 Excellent

"Nice room. Exceptionally clean. Great staff"

Berkshires Untold

10/10 Excellent

"Amazing!"

St. Charles Hotel

8/10 Good

"The room was clean and modern and the staff were friendly and professional. Parking was close and ample."

More cheap stays in Chatham

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.612.737 ₫

1.801.428 ₫ total

30 Sept - 1 Oct

includes taxes & fees

5.4/10 (911 reviews)

Comfort Inn Glenmont - Albany South

37 Route 9W Glenmont NY

2.478.577 ₫

2.837.971 ₫ total

29 Oct - 30 Oct

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

2.626.866 ₫

2.934.209 ₫ total

20 Oct - 21 Oct

includes taxes & fees

8.6/10 Excellent! (1,004 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.804.760 ₫

3.133.021 ₫ total

27 Oct - 28 Oct

includes taxes & fees

9.2/10 Wonderful! (1,016 reviews)

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY

2.847.611 ₫

3.260.515 ₫ total

11 Oct - 12 Oct

includes taxes & fees

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

4.927.585 ₫

6.742.016 ₫ total

26 Oct - 27 Oct

includes taxes & fees

Hotels in Chatham with star rating

Frequently asked questions

What's the seasonal weather in Chatham?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chatham are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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Book Hotels in Chatham on Expedia.com

Find hotels in Chatham, NY from 1.754.927 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chatham

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chatham hotels

1. Chatham Travel Lodge

2. Inn at Silver Maple Farm

3. The Yankee Inn

4. Holiday Inn Express Hotel & Suites West Coxsackie by IHG

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

6. Berkshire Travel Lodge

7. voco James Newbury Hudson Valley by IHG

8. Courtyard by Marriott Lenox Berkshires

9. Best Western Plus Berkshire Hills Inn & Suites

10. Micosta Leisure Inn

11. The Red Lion Inn

12. Berkshires Untold

13. Quality Inn Great Barrington

14. Pocketbook Hotel and Bath

15. Holiday Inn Express Hotel & Suites Great Barrington by IHG

16. Shaker Mill Inn

17. Berkshire Mountain Lodge

18. Spark by Hilton West Coxsackie

19. Prospect Berkshires

20. Comfort Inn & Suites East Greenbush - Albany

Stay near popular Chatham attractions

The Mac-Haydn Theatre

Learn more about Chatham

Top Chatham Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Holiday Inn Club Vacations Oak 'n Spruce Resort

Comfort Inn & Suites East Greenbush - Albany

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Great Barrington

The Red Lion Inn

The Yankee Inn

Berkshires Untold

St. Charles Hotel

More cheap stays in Chatham

FairBridge Inn Express

Comfort Inn Glenmont - Albany South

Quality Inn Great Barrington

The Yankee Inn

Country Inn & Suites by Radisson, Downtown Albany New York

Pocketbook Hotel and Bath

Hotels in Chatham with star rating

Frequently asked questions

Explore a world of travel with Expedia

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