Canaan Holiday Rentals, Connecticut: Private House Rentals

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

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Our top choices for Canaan hotels

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

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

1. Days Inn by Wyndham Torrington

Torrington

Juan

2.527.219 ₫

2.906.302 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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.

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

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

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

Great Barrington

BJORN

2.999.545 ₫

3.350.622 ₫ total

includes taxes & fees

7 Sept - 8 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.

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

Great Barrington

Lisa

4.189.431 ₫

4.679.595 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.

A gym with various exercise equipment, a mirror, and a blue wall.

A spacious living area with a brown leather sofa, a glass coffee table, a wooden entertainment unit with a flat-screen TV, and a large window providing a view of the outdoors.

4. Americas Best Value Inn Torrington CT

Torrington

Carol

3.389.879 ₫

3.898.400 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

5. Quality Inn Lee - Lenox South

Lee

Christine

2.859.453 ₫

3.194.009 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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

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.

6. The Litchfield Inn

Litchfield

Sandra

8.141.026 ₫

9.362.180 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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 bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

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

7. Locust Tree Bed and Breakfast LLC

East Canaan

Regina

2.738.190 ₫

3.148.919 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

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

A motel with a parking lot and several cars parked.

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

8. Monument Mountain Motel

Great Barrington

John

2.229.669 ₫

2.490.449 ₫ 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 grand hallway with a chandelier, a staircase, and a table with flowers.

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

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

9. Blackberry River Inn

Norfolk

Rachel

4.954.820 ₫

5.698.043 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

A two-story building with a sign for Cornwall Inn, featuring a front porch and a mailbox.

A covered patio with a wooden table and chairs, a sofa, and a ceiling fan.

A hotel room with a large bed, two bedside lamps, a chair, a small table, and a rug.

10. Cornwall Inn and Lodge

Cornwall Bridge

"Liked we had a room away from the main building which was quiet and had a private porch. Charming decor with antiques. We really enjoyed the breakfast room and meeting the other guests in the morning and exchanging information on local sites and restaurants. The pool was very refreshing after a hot day. We loved sitting on the porch for breakfast and evening drinks. Getting AC to run consistently was a challenge."

Judith

5.518.105 ₫

6.345.821 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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 tented area with lush greenery and a dining setup.

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

11. Interlaken Inn & Resort

Lakeville

Stacie

5.609.378 ₫

6.450.784 ₫ total

includes taxes & fees

22 Sept - 23 Sept

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

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

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.

12. Little Cat Lodge

Copake Falls

Kees

4.670.570 ₫

5.231.039 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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 living room with a patterned carpet, two sofas, a dining table, and chairs.

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

13. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Elspeth

2.060.162 ₫

2.301.200 ₫ total

includes taxes & fees

1 Sept - 2 Sept

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

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.

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

A covered porch with a dining area, a sofa, and decorative wall art.

14. The White Hart

Salisbury

William

8.953.881 ₫

10.296.898 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

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.

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

15. Quality Inn Great Barrington

Great Barrington

Sisile

2.416.127 ₫

2.698.813 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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

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

16. the Alander

Copake

Phil

4.433.260 ₫

4.965.250 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

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

A living room with a sofa, armchair, coffee table, and a patterned rug.

A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

17. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Claudia

3.051.126 ₫

3.917.959 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A calm lake at dusk with a wooden dock and two chairs facing the water.

A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

18. Berkshire Lake Lodge

Lee

mike

3.911.700 ₫

4.369.369 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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 backyard with a swimming pool, lounge chairs, and a hot tub.

A covered porch with wicker furniture and hanging flower baskets.

19. The Red Lion Inn

Stockbridge

Patricia

4.107.807 ₫

5.883.976 ₫ total

includes taxes & fees

29 Sept - 30 Sept

A bedroom with two beds, a desk, a chair, a window with curtains, and a door with a glass panel.

A room with a mounted television, a chair, and a coat rack.

A bathroom with a large mirror, a lighted frame, and a door.

A bathroom with a white sink, a dark wooden vanity, and a drawer with a white towel.

20. Hitching Post Country Motel

Cornwall Bridge

Chris

3.390.140 ₫

3.898.661 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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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!

See all hotels in Canaan

Top Canaan Hotel Reviews

Quality Inn Lee - Lenox South

10/10 Excellent

"great hotel for the money."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Amazing time. Stayed in the Presidential units. Worth it."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"staff welcoming place clean."

The Litchfield Inn

10/10 Excellent

"Charming older hotel. Wish there were more tv options"

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"It was much better than expected. Subtle lighting in the room was a nice touch. Clean and very comfortable bedding and bathroom. Everything in the fitness room was was clean and operational. The breakfast was superb. A very enjoyable stay."

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."

More cheap stays in Canaan

Monument Mountain Motel

247 Stockbridge Rd Great Barrington MA

2.229.669 ₫

2.490.449 ₫ total

1 Sept - 2 Sept

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

2.416.127 ₫

2.698.813 ₫ total

20 Sept - 21 Sept

includes taxes & fees

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

2.527.219 ₫

2.906.302 ₫ total

31 Aug - 1 Sept

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

2.859.453 ₫

3.194.009 ₫ total

20 Sept - 21 Sept

includes taxes & fees

8.4/10 Very good! (1,003 reviews)

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington MA

2.999.545 ₫

3.350.622 ₫ total

7 Sept - 8 Sept

includes taxes & fees

8.8/10 Excellent! (810 reviews)

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

3.389.879 ₫

3.898.400 ₫ total

31 Aug - 1 Sept

includes taxes & fees

5.6/10 (813 reviews)

Hotels in Canaan with star rating

Frequently asked questions

What's the weather like in Canaan?

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 Canaan are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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Find hotels in Canaan, CT from 2.018.648 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Canaan

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Canaan hotels

1. Days Inn by Wyndham Torrington

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

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

4. Americas Best Value Inn Torrington CT

5. Quality Inn Lee - Lenox South

6. The Litchfield Inn

7. Locust Tree Bed and Breakfast LLC

8. Monument Mountain Motel

9. Blackberry River Inn

10. Cornwall Inn and Lodge

11. Interlaken Inn & Resort

12. Little Cat Lodge

13. Travelodge by Wyndham Great Barrington Berkshires

14. The White Hart

15. Quality Inn Great Barrington

16. the Alander

17. Holiday Inn Club Vacations Oak 'n Spruce Resort

18. Berkshire Lake Lodge

19. The Red Lion Inn

20. Hitching Post Country Motel

Stay near popular Canaan attractions

North Canaan Town Hall

C H Pease Museum

Douglas Library

Edith Scoville Memorial Sanctuary

Lawrence Field

Eddy Field

Connecticut Railroad Historical Museum

Learn more about Canaan

Top Canaan Hotel Reviews

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Red Lion Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Litchfield Inn

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Prospect Berkshires

Americas Best Value Inn Torrington CT

Travelodge by Wyndham Great Barrington Berkshires

More cheap stays in Canaan

Monument Mountain Motel

Quality Inn Great Barrington

Days Inn by Wyndham Torrington

Quality Inn Lee - Lenox South

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Americas Best Value Inn Torrington CT

Hotels in Canaan with star rating

Frequently asked questions

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