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Find hotels in Canaan, NY from ￥13,018

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Dec 14 - Dec 15
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Dec 15 - Dec 16
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Our top choices for Canaan hotels

Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
Experience tranquility at this peaceful B&B in Lee, where deep-tissue massages and aromatherapy await. Just a 10-minute drive from Tanglewood Music Center, guests enjoy access to a hot tub, terrace, and snack bar while exploring nearby Berkshire attractions.
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
Charming Cornell Inn offers a peaceful garden retreat within walking distance to Lenox attractions. Enjoy complimentary gourmet breakfast and unwind with a drink at the bar before retiring to comfortable rooms. Free WiFi and parking enhance your Berkshires getaway.
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is ￥26,035
￥29,953 total
includes taxes & fees
Dec 15 - Dec 16
The Cornell Inn, Lenox & The Berkshires
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
Set amid East Chatham's natural beauty, this charming B&B welcomes guests with daily buffet breakfast and complimentary WiFi. Explore nearby Queechy Lake and Hand Hollow State Forest, with Albany Airport just 44 minutes away.
"Great stay, comfortable place"
United States
barry
The price is ￥20,099
￥22,511 total
includes taxes & fees
Dec 15 - Dec 16
Inn at Silver Maple Farm
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
This centrally located motel has an inviting outdoor pool where you can cool off after exploring nearby attractions. Free WiFi and self parking add extra value while the helpful staff ensures a pleasant stay in clean, comfortable rooms.
"Staff was very friendly and helpful."
United States
Pamela
The price is ￥12,309
￥13,749 total
includes taxes & fees
Dec 15 - Dec 16
Howard Johnson by Wyndham Lenox
Lobby lounge
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (816)
This Lenox lodge combines comfort with convenience, just a short drive from Tanglewood Music Center. The Club Room serves delicious American cuisine, while a welcoming bar and outdoor terrace enhance your stay. Kennedy Park and Pleasant Valley Wilderness Sanctuary await nearby.
"Easiest check in and out. Great food in dining room. "
United States
William
The price is ￥17,084
￥19,083 total
includes taxes & fees
Dec 15 - Dec 16
Berkshires Untold
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
Located in Lee, this inviting B&B offers kayaking adventures and a terrace with lakefront views. Wake up to a full breakfast each morning before exploring nearby attractions like The Mount and Wyndhurst Golf & Club. Helpful staff ensure a memorable stay.
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ￥28,130
￥32,992 total
includes taxes & fees
Dec 19 - Dec 20
Lakehouse Inn
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (707)
Experience comfort in Great Barrington at this welcoming hotel with clean rooms and attentive service. Visit nearby Lake Mansfield Park or explore the Housatonic River after enjoying the indoor pool, fitness center, and complimentary WiFi.
"Great hospitality "
United States
regina maria
The price is ￥16,672
￥18,623 total
includes taxes & fees
Dec 17 - Dec 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (805)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
Tucked in West Stockbridge, this charming B&B offers complimentary morning meals and convenient self parking. Outdoor enthusiasts can explore nearby hiking trails, kayaking spots, and mountain biking routes. Ebenezer II Gifts and Hotchkiss Mobile Studio await just minutes away.
"Nice place, easy check in"
United States
Robert
The price is ￥16,305
￥17,887 total
includes taxes & fees
Dec 18 - Dec 19
Shaker Mill Inn
Exterior
The Whitlock

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (281)
Surrounded by natural beauty, this Lenox hotel offers easy access to Tanglewood Music Center. Explore nearby hiking and biking trails, then unwind on the terrace or garden. Free WiFi and parking enhance your Berkshires adventure.
"great location"
United States
Brian
The price is ￥21,813
￥24,366 total
includes taxes & fees
Dec 23 - Dec 24
The Whitlock
Seasonal outdoor pool
Sunset Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (410)
Discover this charming motel in Lee with free WiFi and parking. The helpful staff ensures a welcoming stay while the seasonal outdoor pool provides refreshment. Nearby attractions include Lee Library and Tanglewood Music Center, with hiking trails waiting for exploration.
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is ￥14,023
￥15,663 total
includes taxes & fees
Dec 15 - Dec 16
Sunset Inn
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (590)
Set in Lenox with easy access to local attractions, this hotel offers an indoor pool and fitness center. Grab a bite at the café or unwind at the bar after exploring Kennedy Park. Rooms include refrigerators and microwaves for added convenience.
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ￥21,034
￥23,496 total
includes taxes & fees
Dec 16 - Dec 17
Courtyard by Marriott Lenox Berkshires
Property entrance
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
Minutes from Barrington Stage Company and Berkshire Athenaeum, this hotel offers comfortable rooms and attentive service. Just a 2-minute walk from Pittsfield Intermodal Transportation Center, enjoy room service and the convenient downtown location.
"Clean room and staff was super friendly"
United States
Yuen
The price is ￥23,216
￥25,932 total
includes taxes & fees
Dec 16 - Dec 17
Hotel On North
Front of property
Brook Farm Inn

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164)
Relax in this Lenox retreat featuring poolside drinks and a garden oasis. Just minutes from Shakespeare and Company, this B&B offers free breakfast, WiFi and parking. Guests consistently praise the attentive staff for an exceptional stay.
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (804)
Nestled in the Berkshires, this family-friendly resort features 2 outdoor and 2 indoor swimming pools. Enjoy refreshments at the pool bar or coffee shop while staying near cultural attractions like Tanglewood Music Center and Berkshire Theatre Festival.
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is ￥18,791
￥24,036 total
includes taxes & fees
Dec 17 - Dec 18
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
The price is ￥21,970
￥31,502 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Red Lion Inn
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Center. After working out in the 24-hour fitness center, savor Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is ￥15,628
￥17,457 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Courtyard
The Springs Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (88)
Embrace the natural charm at this New Ashford motel offering a refreshing seasonal outdoor pool. Free WiFi and parking make exploration easy, with Jiminy Peak Mountain Resort and Brodie Mountain just a short drive away. Enjoy the garden and terrace areas.
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is ￥16,937
￥18,581 total
includes taxes & fees
Dec 15 - Dec 16
The Springs Motel
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2172)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is ￥16,200
￥19,804 total
includes taxes & fees
Dec 15 - Dec 16
Vacation Village in the Berkshires
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
This charming bed and breakfast in Lenox offers a complimentary full breakfast daily. Enjoy free WiFi and parking while staying minutes from Lenox Library and The Bookstore. Pittsfield Municipal Airport is just an 11-minute drive away.
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ￥61,368
￥68,548 total
includes taxes & fees
Jan 11 - Jan 12, 2026
33 Main
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Canaan attractions

Queechy Lake

Commune with nature and explore the great outdoors at Queechy Lake during your travels in Canaan. Discover the area's museums and shops.
See properties

Learn more about Canaan

Nestled in the Berkshire foothills, this charming town offers scenic hikes on Queechy Lake trails and picturesque farm stands along Route 295. Families enjoy swimming at Queechy Beach in summer, while nearby Tanglewood in Lenox hosts renowned classical music performances worth the short trip.

See all hotels in Canaan
Yum
Photo by Robin/Loving Life
Open Photo by Robin/Loving Life

Top Canaan Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Your staff is very courteous and yes my room was spotless. "
FELICA 3-night trip
Posted 14 hours ago
Vacation Village in the Berkshires

More cheap stays in Canaan

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA
The price is ￥11,655 per night from Dec 24 to Dec 25
￥11,655
￥13,018 total
Dec 24 - Dec 25
includes taxes & fees
9/10 Wonderful! (1,002 reviews)

Frequently asked questions

Where is the best place to stay in Canaan?
Vacation Village in the Berkshires, located 13.3 mi (21.4 km) from the heart of Canaan, is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Holiday Inn & Suites Pittsfield-Berkshires by IHG and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Canaan.
What are some of the best vacation home rentals in Canaan?
Pet Friendly Riverfront Home in Great Barrington: This vacation home near Canaan is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games. See all vacation rentals in Canaan.
If I need to cancel my hotel reservation in Canaan, will I receive a refund?
Yes, most room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a reservation that's non-refundable, it might still be possible to cancel it and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Canaan.
Where can I learn more about changing or cancelling my trip to Canaan?
For more information about picking new dates or cancelling your trip to Canaan, click here.
What are some accommodations with pools in Canaan?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG and Berkshire Mountain Lodge are a couple of other choices that feature an onsite pool. View all hotels with pools in Canaan.
What's the best place to stay near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What is staying in Canaan like?
Visitors can enjoy all that Canaan has to offer including the restaurants, coffeehouses, and shopping. Tourists can also enjoy the city's local tours and museums. In Canaan, there are 19 hotels and other accommodations to choose from. Find out more about Canaan.
What should I see while I'm in Canaan?
Favorite places to visit include Queechy Lake, Hollow FIelds Reserve, and Hand Hollow State Forest. Additionally, you might want to add Bates Memorial State Park to your itinerary. Check out what more to see and do in Expedia's Canaan guide.
What's the weather like in Canaan?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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