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

Holiday Homes in Canaan

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Canaan holiday homes

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,004 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is €116
includes taxes & fees
6 Aug - 7 Aug
Best Western Plus Berkshire Hills Inn & Suites
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (112 reviews)
"Very nice hotel."
United States
Erdem
The price is €225
includes taxes & fees
24 Aug - 25 Aug
Inn at Silver Maple Farm
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (496 reviews)
"I have stayed here many times in the past when visiting the area. I feel it is a good value as I am just looking for a place to shower and sleep that is clean and comfortable. The staff will ask, almost daily, if everything is okay or if there is something I need."
United States
George
The price is €66
includes taxes & fees
27 Jul - 28 Jul
Berkshire Travel Lodge
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,018 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
The price is €167
includes taxes & fees
27 Jul - 28 Jul
The Yankee Inn
Balcony

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (232 reviews)
"Great place to stay."
United States
Jurij
The price is €110
includes taxes & fees
26 Jul - 27 Jul
Chatham Travel Lodge
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (464 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is €177
includes taxes & fees
27 Jul - 28 Jul
Shaker Mill Inn
Children’s activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Very comfortable. Will stay there again"
United States
Peter
The price is €62
includes taxes & fees
27 Jul - 28 Jul
Pleasant Valley Motel West Stockbridge
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (890 reviews)
"Great place"
United States
Luciane
The price is €97
includes taxes & fees
26 Jul - 27 Jul
Howard Johnson by Wyndham Lenox
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (895 reviews)
"Very clean and updated simple motel."
United States
christopher
The price is €88
includes taxes & fees
27 Jul - 28 Jul
Berkshire Inn
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,003 reviews)
"Staff was fabulous and extremely helpful and friendly. Valey parking was terrific!!! and FREE Great to have since we had to park at the bank next to the hotel while there was construction in front of the building. Rooms were tidy and very clean Breakfast was excellent with a large variety of offerings"
United States
Margaret
The price is €112
includes taxes & fees
29 Jul - 30 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,023 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is €129
includes taxes & fees
23 Aug - 24 Aug
Berkshire Mountain Lodge
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,010 reviews)
"Nice place to stay."
United States
Debra
The price is €151
includes taxes & fees
24 Aug - 25 Aug
Berkshires Untold
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (145 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is €153
includes taxes & fees
23 Aug - 24 Aug
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (379 reviews)
"Central location!"
United States
Brenda
The price is €105
includes taxes & fees
27 Jul - 28 Jul
The Central Downtown Inn & Suites
BBQ/picnic Area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.8 out of 10, Good, (26 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is €130
includes taxes & fees
26 Jul - 27 Jul
Hideaway Inn Lenox
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (595 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is €97
includes taxes & fees
26 Jul - 27 Jul
Travelodge by Wyndham Great Barrington Berkshires
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (858 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
The price is €61
includes taxes & fees
10 Aug - 11 Aug
FairBridge Inn Express
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"The cornel Inn is terrific! Great location near tanglewood, shops snd restaurants. Great breakfast"
United States
Judith
The price is €222
includes taxes & fees
29 Jul - 30 Jul
The Cornell Inn, Lenox & The Berkshires
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,006 reviews)
"Great place"
United States
Michelle
The price is €133
includes taxes & fees
20 Aug - 21 Aug
Quality Inn Lee - Lenox South
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,008 reviews)
"Fantastic pool to top off the great location and fun historic hotel!"
United States
Antoinette G.
The price is €216
includes taxes & fees
24 Aug - 25 Aug
The Red Lion Inn
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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Top Canaan Hotel Reviews

The Whitlock

The Whitlock

8/10 Good
"Very nice coffee set up in the morning. Staff was super courteous and helpful. Most of property is updated although carpeting and rugs are tired. Location is great, very convenient to Tanglewood and restaurants. Parking is onsite and more than ample. B"
Rebecca 1-night trip
Posted less than an hour ago
The Whitlock

Find out more about Canaan

Canaan Holiday Homes information

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