Top 10 Hotels in Canaan, NY in 2026 (from $74)

A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

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

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

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.

1. Inn at Silver Maple Farm

East Chatham

$184

$206 total

includes taxes & fees

Nov 22 - Nov 23

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

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A wooden cabinet with a coffee maker and a white container.

A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

2. Hampton Inn & Suites Berkshires-Lenox

Lenox

$110

$122 total

includes taxes & fees

Oct 30 - Oct 31

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 reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

3. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

$98

$109 total

includes taxes & fees

Nov 15 - Nov 16

4. Berkshire Travel Lodge

Austerlitz

$75

$84 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

5. The Yankee Inn

Lenox

$106

$118 total

includes taxes & fees

Nov 1 - Nov 2

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

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

6. Chatham Travel Lodge

Old Chatham

$112

$125 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

7. Howard Johnson by Wyndham Lenox

Lenox

$79

$88 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

8. Shaker Mill Inn

West Stockbridge

$122

$134 total

includes taxes & fees

Nov 3 - Nov 4

A hotel room with a bed, two chairs, a small table, and a lamp.

A hotel room with a flat-screen TV, a microwave, a refrigerator, a wooden dresser, a bedside lamp, and a framed picture on the wall.

A reception desk with a framed floral painting, a deer head, and a sign about pets.

A motel with a row of rooms, a parking lot, and a hilly backdrop.

9. Pleasant Valley Motel West Stockbridge

West Stockbridge

$77

$84 total

includes taxes & fees

Oct 25 - Oct 26

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A modern cafe with a counter, seating area, and large windows.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

10. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

$99

$111 total

includes taxes & fees

Nov 22 - Nov 23

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

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

A garden with wooden Adirondack chairs and a stone pathway.

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

11. Berkshire Mountain Lodge

Pittsfield

$95

$128 total

includes taxes & fees

Nov 22 - Nov 23

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

A modern restaurant with wooden flooring, bar area, and seating arrangements.

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

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

12. Courtyard by Marriott Lenox Berkshires

Lenox

$126

$140 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

13. Element by Marriott Lenox Berkshires

Lenox

$135

$151 total

includes taxes & fees

Nov 8 - Nov 9

A hotel patio with outdoor seating and a fire pit.

A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

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

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

14. Hilton Garden Inn Lenox Pittsfield

Pittsfield

$128

$143 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A motel with a parking lot, a swimming pool, and outdoor seating.

A fenced outdoor area with a pool, lounge chairs, and umbrellas.

15. Berkshire Inn

Pittsfield

$86

$96 total

includes taxes & fees

Oct 25 - Oct 26

16. Garden Gables

Lenox

$134

$149 total

includes taxes & fees

Oct 25 - Oct 26

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.

17. Berkshires Untold

Lenox

$133

$149 total

includes taxes & fees

Nov 3 - Nov 4

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

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

18. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

$115

$128 total

includes taxes & fees

Nov 15 - Nov 16

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

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

19. Quality Inn Lee - Lenox South

Lee

$93

$103 total

includes taxes & fees

Nov 11 - Nov 12

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

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

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.

20. The Cornell Inn, Lenox & The Berkshires

Lenox

$156

$179 total

includes taxes & fees

Oct 27 - Oct 28

View all properties

Go beyond your typical stay in Canaan

Top landmarks in Canaan

Queechy Lake

Queechy Lake is 1.7 mi (2.7 km) from central Canaan, why not stop by during your stay.

See properties

Learn more about Canaan

Canaan is well-known for its attractions such as Queechy Lake and Hollow FIelds Reserve.

See all hotels in Canaan

Check out reviews of Canaan hotels guests love

Inn at Silver Maple Farm

East Chatham

10/10 Exceptional

Michelle

Hampton Inn & Suites Berkshires-Lenox

Lenox

10/10 Exceptional

Colton

Shaker Mill Inn

West Stockbridge

10/10 Exceptional

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

The Yankee Inn

Lenox

10/10 Exceptional

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Exceptional

Gregory

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

10/10 Exceptional

Bruce

Element by Marriott Lenox Berkshires

Lenox

10/10 Exceptional

Jacqueline

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Exceptional

Alyssa

Berkshire Mountain Lodge

Pittsfield

10/10 Exceptional

Elliott

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

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.

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 Exceptional

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Exceptional

Berkshires Untold

Lenox

10/10 Exceptional

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Exceptional

Lawrence

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Exceptional

Sheila

Chatham Travel Lodge

Old Chatham

10/10 Exceptional

Anonymous traveler

A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

A window view of a garden with rocks, bushes, and trees.

A white bench with bright pink cushions, a small potted plant, and decorative wall art including a sun and a crescent moon.

A red door with a wreath, number 5, and flower baskets on either side.

The Red Door B&B

Lee

10/10 Exceptional

Rudi

Quality Inn Lee - Lenox South

Lee

10/10 Exceptional

Anonymous traveler

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

Brook Farm Inn

Lenox

10/10 Exceptional

roberta

Frequently Asked Questions

What accommodations do travelers like in Canaan?

Guests like Berkshire Mountain Lodge, The Yankee Inn and Berkshires Untold.

Can I book refundable hotels in Canaan?

If you need the flexibility to change your plans to Canaan, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Canaan if I want a vacation home instead of a traditional hotel?

Browse 7 vacation homes on our site.

What will the weather in Canaan be like during my visit?

July and August are typically the warmest months in Canaan when the average temp is 66°F. January and February are the coldest months when the average temperature is 27°F. October and August are the months with the most rain.

Why should I book my Canaan hotel through Hotels.com?

There are lots of reasons to book your Canaan trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.