𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Canaan from RM321 (2026) - Fully Refundable Options

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

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Go beyond your typical stay in Canaan

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Our top choices for Canaan hotels

A Holiday Inn Express & Suites building with a stone facade, a covered entrance, and a parking lot.

An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.

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

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

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

Great Barrington

BJORN

RM497

RM555 total

includes taxes & fees

23 Sept - 24 Sept

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

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

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.

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

Great Barrington

Lisa

RM786

RM878 total

includes taxes & fees

1 Sept - 2 Sept

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 covered porch with white railings and rocking chairs.

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

3. Locust Tree Bed and Breakfast LLC

East Canaan

Regina

RM424

RM488 total

includes taxes & fees

1 Sept - 2 Sept

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

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

A grand hallway with a chandelier, a staircase, and a table with flowers.

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

4. Blackberry River Inn

Norfolk

Rachel

RM767

RM882 total

includes taxes & fees

31 Aug - 1 Sept

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

A bedroom with a large bed, a dresser, a chair, and a mirror.

5. Wilder House Berkshires

Sheffield

Jennifer

RM779

RM870 total

includes taxes & fees

27 Aug - 28 Aug

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

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'.

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

6. Quality Inn Great Barrington

Great Barrington

Sisile

RM374

RM418 total

includes taxes & fees

14 Sept - 15 Sept

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

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

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

A house with a stone patio and wooden stools.

7. Little Cat Lodge

Copake Falls

Kees

RM797

RM892 total

includes taxes & fees

26 Aug - 27 Aug

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

A tented area with lush greenery and a dining setup.

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

A modern hotel room with a bed, sofa, leather chair, and a small table.

8. Interlaken Inn & Resort

Lakeville

Stacie

RM870

RM1,000 total

includes taxes & fees

22 Sept - 23 Sept

A bedroom with a large bed, a chair, and a window with curtains.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.

9. The White Hart

Salisbury

William

RM1,387

RM1,595 total

includes taxes & fees

1 Sept - 2 Sept

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

A bathroom with a bathtub, toilet, and granite countertop sink.

A kitchen area with a counter, a microwave, a coffee machine, and a display case with pastries.

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

10. Days Inn by Wyndham Torrington

Torrington

Juan

RM375

RM431 total

includes taxes & fees

27 Aug - 28 Aug

A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.

A spacious living room with a fireplace, patterned armchairs, and a staircase leading to an upper level.

A rustic barn-style venue with round tables and chairs, string lights, and a central bar area.

A wooden sign with "GEDNEY FARM" written on it, surrounded by lush greenery and purple flowers.

11. Gedney Farm

Great Barrington

Jane

RM928

RM1,018 total

includes taxes & fees

26 Aug - 27 Aug

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 modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.

12. the Alander

Copake

Tom

RM687

RM769 total

includes taxes & fees

1 Sept - 2 Sept

A patio with a round metal table, a glass of white wine, and a red umbrella.

A grand staircase with a wooden railing, leading to a room with large windows and a patterned ceiling.

A dining table with a plate of food and two wine glasses, set in a room with leather furniture and a fireplace in the background.

A cozy room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

13. Manor House Inn

Norfolk

Kevin

RM1,329

RM1,475 total

includes taxes & fees

22 Sept - 23 Sept

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 long dining table set with multiple wine glasses, water glasses, and folded white napkins.

14. The Millerton Inn

Millerton

Bernadette

RM1,014

RM1,147 total

includes taxes & fees

30 Aug - 31 Aug

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

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.

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

15. Monument Mountain Motel

Great Barrington

John

RM346

RM386 total

includes taxes & fees

1 Sept - 2 Sept

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

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

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

16. Quality Inn Lee - Lenox South

Lee

Christine

RM443

RM495 total

includes taxes & fees

14 Sept - 15 Sept

A lobby with a chandelier, a reception desk, and a sign indicating an exit.

A white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

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

A rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.

17. The Litchfield Inn

Litchfield

Sandra

RM1,155

RM1,328 total

includes taxes & fees

26 Aug - 27 Aug

A large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

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

18. The Little Lion

Great Barrington

Anne

RM454

RM507 total

includes taxes & fees

1 Sept - 2 Sept

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

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.

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

19. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Elspeth

RM319

RM357 total

includes taxes & fees

1 Sept - 2 Sept

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

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

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

20. East Rock Inn

Great Barrington

ERIK

RM527

RM589 total

includes taxes & fees

8 Sept - 9 Sept

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Stay near popular Canaan attractions

North Canaan Town Hall

North Canaan Town Hall serves as the centre of local government operations in this small Connecticut town. Its modest architecture reflects the practical, community-focused character of the area.

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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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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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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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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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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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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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Learn more about Canaan

Love the countryside and dining? Get away to Canaan!

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Top Canaan Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"Our family loves this hotel! Hot tub and pool are excellent. There’s a fun little game room for kids. The breakfast was plentiful and tasty. Everything is clean and staff is nice. Best part- four working level 2 car chargers!"

Monument Mountain Motel

8/10 Good

"Everything was fine except for the spotty WIFI. I was frustrated by how frequent their were interruptions in WIFI service. The WIFI is free but very faulty, as I couldn't get any work done during my stay. I would have preferred to pay for the WIFI just so I could have proper service."

the Alander

10/10 Excellent

"This was an idyllic escape out of the city for a bit. The restaurant was great, the owners are considerate, kind and accommodating and the view from the property is breathtaking. We needed something low key and restorative and we got it. Looking forward to returning the next time we need a getaway."

Days Inn by Wyndham Torrington

8/10 Good

"Pretty loud AC"

Quality Inn Lee - Lenox South

8/10 Good

"Clean room, surprisingly comfortable bed. Convenient, functional, for a short stay."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Oak’n’Spruce is a lovely resort in a wonderful area of the Berkshires. Very nice amenities, along with pools, tennis, mini golf, ping pong and other family activities. Best of all, it’s a short drive to the charming town of Stockbridge, a short drive to Tanglewood, and another short drive to Jacob’s pillow, a wonderful indoor and outdoor dance performance venue. We stay there often, and always makes four a cultural experience and wonderful family time."

Prospect Berkshires

10/10 Excellent

"It was beautiful but quite expensive. There was no housekeeping included so trash was not picked up and the breakfasts were grossly overpriced!"

Americas Best Value Inn Torrington CT

10/10 Excellent

"All the staff members I met were cheerful & helpful. I asked for a ground floor room, upon arrival, got a very nice one at no extra charge. I was in the area for a music festival, plan on booking a stay again , next year."

Travelodge by Wyndham Great Barrington Berkshires

8/10 Good

"We did not use the amenities. We were only there to sleep and for one night, but the staff was friendly and the room was cleanly enough."