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.

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.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

Great Barrington

Kelly

3.719.529 ₫

4.154.715 ₫ 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 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.

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

2. Quality Inn Great Barrington

Downtown Great Barrington

Joan

1.942.234 ₫

2.169.476 ₫ 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 hotel room with two beds, a desk, a TV, and a window with curtains.

A coffee station with two coffee machines and a variety of coffee pods and cups.

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

Great Barrington

Maria Dulce

2.151.028 ₫

2.402.697 ₫ total

includes taxes & fees

12 Nov - 13 Nov

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

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

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.

4. Blackberry River Inn

Norfolk

Donna

4.919.670 ₫

5.657.620 ₫ total

includes taxes & fees

22 Oct - 23 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 dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

5. The White Hart

Salisbury

William

7.993.169 ₫

9.192.274 ₫ 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

6.967.806 ₫

8.012.977 ₫ 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 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.

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

7. Monument Mountain Motel

Great Barrington

Andrea

1.549.696 ₫

1.730.947 ₫ total

includes taxes & fees

3 Nov - 4 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.

8. Wilder House Berkshires

Sheffield

Mark

4.242.905 ₫

4.739.324 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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

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

A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

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

9. The Old Inn On The Green

Great Barrington

Catherine

7.508.970 ₫

9.060.996 ₫ total

includes taxes & fees

10 Nov - 11 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 bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

A covered porch with white railings and rocking chairs.

10. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

2.718.765 ₫

3.126.580 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

A wooden wall with a white pendant light fixture.

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

7.340.665 ₫

9.067.197 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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

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.

12. Quality Inn Lee - Lenox South

Lee

Christine

2.398.986 ₫

2.679.668 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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 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.

13. the Alander

Copake

Joseph

4.272.345 ₫

4.785.026 ₫ total

includes taxes & fees

13 Nov - 14 Nov

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

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

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

14. Manor House Inn

Norfolk

Kevin

9.036.657 ₫

10.030.689 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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

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.

15. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

2.045.547 ₫

2.284.876 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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.

16. The Millerton Inn

Millerton

Chelsy

6.501.732 ₫

7.355.085 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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.

17. East Rock Inn

Great Barrington

ERIK

3.258.323 ₫

3.639.546 ₫ total

includes taxes & fees

15 Nov - 16 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.

18. Little Cat Lodge

Copake Falls

Stacy

3.938.325 ₫

4.410.924 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A large house with a balcony and a grassy yard.

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

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.

19. The Little Lion

Great Barrington

Lidia

2.679.925 ₫

2.993.476 ₫ 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

15.373.969 ₫

17.680.064 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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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!

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Top Canaan Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Perfect place for our two night stay. Good location for exploring the local area. The room was clean and spacious. Good restaurants nearby and there was plenty of parking. Staff were friendly and helpful."

Quality Inn Great Barrington

10/10 Excellent

"good location, friendly helpful staff"

Quality Inn Lee - Lenox South

8/10 Good

"Had a comfortable stay."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Nice place to stay"

Little Cat Lodge

10/10 Excellent

"Beyond amazing, we loved it so much!"

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"

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"Excellent room! Clean and good breakfast!"

Prospect Berkshires

10/10 Excellent

"Absolutely spectacular resort! Could not have enjoyed more."

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."