𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Canaan (2026)

A red bridge over a river with snow patches and dry grass.

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Our top choices for Canaan hotels

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

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

1. Quality Inn Great Barrington

Downtown Great Barrington

Joan

S$111

includes taxes & fees

10 Nov - 11 Nov

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

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

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

Great Barrington

Maria Dulce

S$119

includes taxes & fees

10 Nov - 11 Nov

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

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

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.

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

Great Barrington

Kelly

S$205

includes taxes & fees

2 Nov - 3 Nov

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

A motel with a parking lot and several cars parked.

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

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

4. Monument Mountain Motel

Great Barrington

Andrea

S$86

includes taxes & fees

1 Nov - 2 Nov

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

A two-story building with a flat roof, solar panels, and a small patio area.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

A covered porch with white railings and rocking chairs.

5. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

S$155

includes taxes & fees

14 Oct - 15 Oct

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

A room with a fireplace, two striped armchairs, and a floral drape.

6. Blackberry River Inn

Norfolk

Donna

S$280

includes taxes & fees

26 Oct - 27 Oct

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

7. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

S$113

includes taxes & fees

18 Oct - 19 Oct

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

A dog standing at a door entrance with a wooden floor and a mat with paw prints.

A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

8. the Alander

Copake

Joseph

S$244

includes taxes & fees

14 Oct - 15 Oct

A large house with a balcony and a grassy yard.

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

9. The Little Lion

Great Barrington

Lidia

S$148

includes taxes & fees

18 Oct - 19 Oct

A wooden deck with a swing chair and a bench overlooking a lake.

A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

A modern bar area with a counter, bar stools, and a variety of bottles.

A tented area with lush greenery and a dining setup.

10. Interlaken Inn & Resort

Lakeville

Stacie

S$396

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

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

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

11. Quality Inn Lee - Lenox South

Lee

Christine

S$133

includes taxes & fees

2 Nov - 3 Nov

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

12. East Rock Inn

Great Barrington

ERIK

S$178

includes taxes & fees

12 Nov - 13 Nov

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

A house with a stone patio and wooden stools.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

13. Little Cat Lodge

Copake Falls

Stacy

S$205

includes taxes & fees

12 Nov - 13 Nov

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

14. Wilder House Berkshires

Sheffield

Mark

S$268

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a desk, and two wall-mounted lamps.

A hotel room with a bed, two bedside tables, a desk, two chairs, and a large window with a view of greenery.

A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

A motel with a central entrance, a flag, and a parking area with several cars.

15. Econo Lodge Lee - Great Barrington

Lee

Anna

S$94

includes taxes & fees

6 Nov - 7 Nov

A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.

A Days Inn building with a blue awning, a lobby entrance, and a well-maintained lawn with various plants.

A Days Inn sign with a sunburst design, surrounded by trees.

A breakfast bar with a coffee machine, toaster, and various food items.

16. Days Inn by Wyndham Torrington

Torrington

Alyson

S$136

includes taxes & fees

1 Nov - 2 Nov

A building with a porch and multiple windows, surrounded by purple flowers.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A café with a display case, a frozen food section, and a marketplace sign.

17. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

Jared

S$192

includes taxes & fees

22 Oct - 23 Oct

A dining area with round tables set for two, a fireplace, and a mural on the wall.

A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

A white two-story house with a front door, windows, and a chimney.

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

18. The Old Inn On The Green

Great Barrington

Catherine

S$448

includes taxes & fees

1 Nov - 2 Nov

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

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.

A bar with wooden floors and shelves filled with bottles.

19. The Red Lion Inn

Stockbridge

Stephan

S$289

includes taxes & fees

3 Nov - 4 Nov

An outdoor patio with a fire pit, seating, and umbrellas.

A two-story building with a balcony, outdoor seating area with umbrellas, and potted plants.

A bedroom with a bed, a sofa, a wooden bench, a window, and a door.

A bedroom with a large bed, a dresser, a chair, and a table. There are three windows with blinds, and a lamp is on a nightstand.

20. The Millerton Inn

Millerton

Chelsy

S$364

includes taxes & fees

20 Oct - 21 Oct

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Stay near popular Canaan attractions

C H Pease Museum

This Victorian-era natural history collection showcases meticulously preserved local wildlife from the 1800s. Examine rare bird specimens and vintage taxidermy in North Canaan's historic Douglas Library.

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Connecticut Railroad Historical Museum

Housed in the restored Canaan Union Station, this museum showcases the region's railway heritage through vintage artefacts. Model trains and historical photographs transport you to the golden age of rail travel.

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Edith Scoville Memorial Sanctuary

Traverse lush forests to Lion's Head Peak at this tranquil Connecticut sanctuary. The challenging trail rewards hikers with panoramic views of rolling hills and vibrant fall foliage.

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Douglas Library

Douglas Library, established in 1821, stands as one of Connecticut's oldest public libraries with 17,000 volumes. Browse the local history collection or join community events like storey hours and art exhibitions.

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Eddy Field

Sam Eddy Field offers tennis courts and volleyball facilities in a relaxed community setting. Bring your own sports equipment and enjoy the park's proximity to the town pool for a complete recreational experience.

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Lawrence Field

Lawrence Field hosts thrilling dog sport competitions for participants of all skill levels. Spectators can enjoy the vibrant atmosphere while watching remarkable displays of canine athleticism and teamwork.

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Learn more about Canaan

Love the countryside and dining? Get away to Canaan!

See all hotels in Canaan

Top Canaan Hotel Reviews

Quality Inn Lee - Lenox South

10/10 Excellent

"The rooms were clean and parking what’s convenient."

Quality Inn Great Barrington

10/10 Excellent

"Beds were comfortable, room was clean, train was not often"

The Litchfield Inn

10/10 Excellent

"Quite simply excellent. This was an overnight stop on our Fall Foliage tour of New England this year. It is not often that I can't think of something that could be improved but nothing comes to mind about this place."

Little Cat Lodge

10/10 Excellent

"Beyond amazing, we loved it so much!"

the Alander

10/10 Excellent

"We absolutely loved our two nights at the Alander, Jason, Reid, and Presley were amazing and kind and we absolutely encourage anyone thinking to stay here to do so!"

The Abner Hotel

10/10 Excellent

"The hotel is an old courthouse with an incredible charm. It is spacious and comfortable. It has the feel of old time charm yet it is brand new. The staff could not have been more helpful and pleasant. We really enjoyed our stay and will certainly go back!"

Monument Mountain Motel

8/10 Good

"This was a fine place for a one-night stay while passing through the area. The room was nothing special, but it was clean and comfortable. The morning breakfast had rather limited selections."

Days Inn by Wyndham Torrington

8/10 Good

"Dated building and area , no elevator , towels not replaced daily , no exter to in room , min. On roll provided , yogurt, fruit cup , and carbs for breakfast , no juice"

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

More cheap stays in Canaan

Quality Inn Great Barrington

372 Main Street Great Barrington MA

S$111

10 Nov - 11 Nov

includes taxes & fees