Canaan Holiday Homes from €126: Search Top House Rentals

A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

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Our top choices for Canaan holiday homes

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

1. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Varun M.

includes taxes & fees

11 Sept - 12 Sept

A spacious living room with a dining area, a kitchen, and a large window.

2. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

includes taxes & fees

9 Oct - 10 Oct

A white two-story house with a porch, surrounded by trees and a hill.

3. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

includes taxes & fees

13 Sept - 14 Sept

A spacious room with a wooden ceiling, large windows, and a chandelier.

4. Luxury Barn Retreat — All-Season Escape Awaits!

East Chatham

Michael T.

includes taxes & fees

15 Sept - 16 Sept

A camping setup with a metal chair and a table by a river in a forest.

5. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

Jess S.

includes taxes & fees

11 Oct - 12 Oct

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Diego G.

includes taxes & fees

13 Sept - 14 Sept

A modern building with a wooden deck and a door.

7. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

8. NEW RENO Historic Creamery in Berkshires w/hot tub

New Lebanon

Anonymous traveller

includes taxes & fees

14 Sept - 15 Sept

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

9. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

10. Riverside Retreat in the Berkshires

Great Barrington

Colin E.

includes taxes & fees

21 Sept - 22 Sept

A wooden deck with a staircase leading to a covered porch area.

11. All the comforts of home

Hudson

Julie B.

includes taxes & fees

14 Sept - 15 Sept

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

15 Sept - 16 Sept

A wooden deck with a table and chairs, surrounded by a white railing.

13. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Ann C.

includes taxes & fees

11 Sept - 12 Sept

14. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Maura L.

includes taxes & fees

11 Sept - 12 Sept

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

15. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

includes taxes & fees

15 Sept - 16 Sept

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

16. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveller

includes taxes & fees

28 Sept - 29 Sept

A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

17. Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

SteveS

includes taxes & fees

14 Sept - 15 Sept

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

18. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

includes taxes & fees

14 Sept - 15 Sept

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

19. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

includes taxes & fees

21 Sept - 22 Sept

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

20. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Rebecca K.

includes taxes & fees

24 Sept - 25 Sept

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Top Canaan Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Very nice hotel. I would definitely stay here again."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

Find out more about Canaan

Canaan Holiday Homes information

Number of reviews	225
Accommodation	428 Holiday Homes
Lowest Price	€126
Highest Price	€1,143

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Canaan holiday homes

1. NEW RENO - Chalet-style farm loft near Tanglewood

2. 1800s Carriage house in Berkshires / Hudson Valley

3. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

4. Luxury Barn Retreat — All-Season Escape Awaits!

5. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

7. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8. NEW RENO Historic Creamery in Berkshires w/hot tub