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

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

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

Great Barrington

3.718.380 ₫

4.153.430 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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 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.

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

2. Quality Inn Great Barrington

Downtown Great Barrington

Scott Patterson

1.958.200 ₫

2.187.309 ₫ total

includes taxes & fees

8 Nov - 9 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 coffee station with two coffee machines and a variety of coffee pods and cups.

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

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

Great Barrington

Cynthia

2.148.455 ₫

2.399.824 ₫ total

includes taxes & fees

17 Nov - 18 Nov

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

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

4. Blackberry River Inn

Norfolk

Donna

4.915.870 ₫

5.653.250 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

5. The White Hart

Salisbury

William

7.990.700 ₫

9.189.434 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

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

6. Interlaken Inn & Resort

Lakeville

Stacie

6.965.653 ₫

8.010.501 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A motel with a parking lot and several cars parked.

7. Monument Mountain Motel

Great Barrington

Andrea

1.549.217 ₫

1.730.412 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

8. Wilder House Berkshires

Sheffield

Mark

4.491.099 ₫

5.016.558 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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 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.

9. the Alander

Copake

Luis

3.623.900 ₫

4.058.768 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

10. The Old Inn On The Green

Great Barrington

Catherine

7.506.650 ₫

9.058.197 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

11. Prospect Berkshires

Egremont

Conor

7.338.397 ₫

9.064.396 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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

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

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

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

12. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

2.043.967 ₫

2.283.111 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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.

13. Quality Inn Lee - Lenox South

Lee

Lucinda

2.398.245 ₫

2.678.839 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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.

14. The Millerton Inn

Millerton

Chelsy

6.496.710 ₫

7.349.402 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A large, two-story house with a steeply pitched roof, stone foundation, and a well-maintained garden with various shrubs and a fountain.

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

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

15. Manor House Inn

Norfolk

Kevin

9.033.865 ₫

10.027.591 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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

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.

16. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

2.716.665 ₫

3.124.165 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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

17. East Rock Inn

Great Barrington

Sharon

3.257.317 ₫

3.638.423 ₫ total

includes taxes & fees

17 Nov - 18 Nov

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

18. Little Cat Lodge

Copake Falls

Stacy

3.937.108 ₫

4.409.560 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

19. The Little Lion

Great Barrington

Lidia

2.679.097 ₫

2.992.552 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with a dining area, a large window, and a view of the garden.

A modern kitchen with a wooden dining table, chairs, a pendant light, and a black countertop with a coffee maker and a plant.

A modern outdoor dining area with a round table and white chairs, surrounded by lush greenery and a white railing.

A white building with a number '9' sign, a covered entrance, and six planters with shrubs.

20. 9 Academy

Salisbury

Kyle

15.362.094 ₫

17.666.409 ₫ total

includes taxes & fees

25 Oct - 26 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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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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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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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

The Red Lion Inn

10/10 Excellent

"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good

"Property grounds weren’t maintained well. Bathroom faucet was lose."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"We were able to get rental as a last minute deal for a villa here and we're very pleased with the property. The two rooms were very spacious each with its own bathroom, one with jacuuzi. Was quiet and you don't see or hear neighbor next to you. The rooms were quite roomy. All amenities in kitchen and nice livingroom/dining area. Nice outdoor seating with table and nice view of mountains. Only issue encountered was figuring out how the showers worked, figured it out by pulling down a round lever on bottom of faucet. Very clean and spacious, nice experience."

Days Inn by Wyndham Torrington

10/10 Excellent

"I loved the indoor pool, the breakfast and the housekeeping! The front desk was amazing and very helpful"

Quality Inn Great Barrington

8/10 Good

"The hotel is in a good location. There are some good restaurants within walking distance. Only one complaint is that the bathroom fan is very loud."

Quality Inn Lee - Lenox South

8/10 Good

"Pleasant stay, nice and clean conditions."

Belden House & Mews

10/10 Excellent

"The staff the rooms the atmosphere location the FOOD. Well deserved best hotel in the state by far."

Blackberry River Inn

10/10 Excellent

"A beautiful, clean country inn with a delicious breakfast."

Little Cat Lodge

10/10 Excellent

"Beyond amazing, we loved it so much!"

More cheap stays in Canaan

Quality Inn Great Barrington

372 Main Street Great Barrington MA

1.958.200 ₫

2.187.309 ₫ total

8 Nov - 9 Nov

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington MA

2.148.455 ₫

2.399.824 ₫ total

17 Nov - 18 Nov

includes taxes & fees

8.8/10 Excellent! (839 reviews)

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

2.200.225 ₫

2.530.258 ₫ total

12 Nov - 13 Nov

includes taxes & fees

7.4/10 Good! (1,004 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

2.398.245 ₫

2.678.839 ₫ total

8 Nov - 9 Nov

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

3.363.231 ₫

3.867.755 ₫ total

21 Oct - 22 Oct

includes taxes & fees

5.6/10 (827 reviews)

the Alander

7519 NY-22 Copake NY

3.623.900 ₫

4.058.768 ₫ total

19 Oct - 20 Oct

includes taxes & fees

9/10 Wonderful! (282 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 1.730.412 ₫

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

2. Quality Inn Great Barrington

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

4. Blackberry River Inn

5. The White Hart

6. Interlaken Inn & Resort

7. Monument Mountain Motel

8. Wilder House Berkshires

9. the Alander

10. The Old Inn On The Green

11. Prospect Berkshires

12. Travelodge by Wyndham Great Barrington Berkshires

13. Quality Inn Lee - Lenox South

14. The Millerton Inn

15. Manor House Inn

16. Locust Tree Bed and Breakfast LLC

17. East Rock Inn

18. Little Cat Lodge

19. The Little Lion

20. 9 Academy

Stay near popular Canaan attractions

C H Pease Museum

Connecticut Railroad Historical Museum

Eddy Field

Edith Scoville Memorial Sanctuary

Douglas Library

Lawrence Field

Learn more about Canaan

Top Canaan Hotel Reviews

The Red Lion Inn

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Club Vacations Oak 'n Spruce Resort

Days Inn by Wyndham Torrington

Quality Inn Great Barrington

Quality Inn Lee - Lenox South

Belden House & Mews

Blackberry River Inn

Little Cat Lodge

More cheap stays in Canaan

Quality Inn Great Barrington

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Days Inn by Wyndham Torrington

Quality Inn Lee - Lenox South

Americas Best Value Inn Torrington CT

the Alander

Hotels in Canaan with star rating

Frequently asked questions

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