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Our top choices for West Stockbridge hotels

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Very cute and clean room."
United States
Karen
Travelling with family
The price is AU$173
includes taxes & fees
17 Dec - 18 Dec
Shaker Mill Inn

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1002)
"Fit my needs like a tailored suit: inexpensive. room was acceptable"
United States
Albert
The price is AU$87
includes taxes & fees
1 Jan - 2 Jan 2026
Pleasant Valley Motel West Stockbridge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Do hotel, very clean we had a great day"
United States
Brian
The price is AU$206
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (788)
"Room was very clean and there is a shopping area close by which made it convenient."
United States
Abraham
Travelling for leisure
The price is AU$199
includes taxes & fees
8 Jan - 9 Jan 2026
Berkshire Mountain Lodge

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Bed was very comfortable"
United States
Michael
Travelling solo
The price is AU$182
includes taxes & fees
16 Dec - 17 Dec
Locust Tree Bed and Breakfast LLC

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
"Room was clean and incredibly comfortable."
United States
Jessica
Travelling for leisure
The price is AU$250
includes taxes & fees
16 Dec - 17 Dec
Hotel On North

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Lovely hotel, room was great along with the staff and the grounds where beautiful."
United States
Vicki
Travelling for leisure
The price is AU$173
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Lenox Pittsfield

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, (1001)
"This hotel was clean, very comfortable beds, and had a great breakfast."
United States
Thomas
Travelling for leisure
The price is AU$128
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Spacious, and the dog friendly suite was a great experience."
United States
Maria
Travelling with pet
The price is AU$150
includes taxes & fees
16 Dec - 17 Dec
The Central Downtown Inn & Suites

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (816)
"The room was perfect for two of us, had all the basic amenities and was charming."
United States
Emily
Travelling for leisure
The price is AU$184
includes taxes & fees
16 Dec - 17 Dec
Berkshires Untold

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (987)
"Rooms were clean and dishes well stocked in the kitchenette"
United States
Sandhya
Travelling for leisure
The price is AU$314
includes taxes & fees
17 Dec - 18 Dec
Jiminy Peak Mountain Resort

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1001)
"The hotel room is space, clean and bright, love it."
United States
Tie Bing
Travelling with family
The price is AU$181
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1003)
"Rooms are clean and comfortable"
United States
Erin
Travelling with family
The price is AU$126
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
The price is AU$342
includes taxes & fees
7 Jan - 8 Jan 2026
Harbour House Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"The bed was very comfortable."
United States
Tracy
Travelling with partner
The price is AU$134
includes taxes & fees
23 Dec - 24 Dec
Berkshire Inn

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Room was very cozy and beautiful."
United States
Kiersten
The price is AU$272
includes taxes & fees
16 Dec - 17 Dec
Wilder House Berkshires

The White Hart

The White Hart
4.0 star property
Salisbury
9.6 out of 10, Exceptional, (143)
"Great charming place, friendly, helpful staff"
United States
David
The price is AU$361
includes taxes & fees
17 Dec - 18 Dec
The White Hart

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (12)
"New hotel very nice"
United States
joel
The price is AU$220
includes taxes & fees
21 Dec - 22 Dec
Element Lenox Berkshires

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"the room was clean, quiet and comfortable"
United States
margaret
Travelling with partner
The price is AU$284
includes taxes & fees
17 Dec - 18 Dec
Blackberry River Inn

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (590)
"our daughter was so excited to use the pool"
United States
Marlene
Travelling for leisure
The price is AU$227
includes taxes & fees
17 Dec - 18 Dec
Courtyard by Marriott Lenox Berkshires
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 West Stockbridge attractions

Learn more about West Stockbridge

The historic Turn Park Art Space showcases outdoor sculptures along winding paths overlooking the Housatonic River. Grab breakfast at Six Depot Roastery before browsing the charming shops and galleries along Main Street.

Olivias Overlook - West Stockbridge, Massachusetts

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Recent Reviews in West Stockbridge

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Frequently asked questions

What's the best place to stay in West Stockbridge?
Shaker Mill Inn is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Pleasant Valley Motel West Stockbridge is another good choice for your stay. See all available top hotels, or vacation rentals in West Stockbridge.
What are some of the best holiday rentals that West Stockbridge has to offer?
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This highly rated holiday home rental in West Stockbridge is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. See all vacation rentals in West Stockbridge.
If I need to cancel my hotel reservation in West Stockbridge, will I receive a refund?
Yes! You'll find that most hotel reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in West Stockbridge.
What is the top LGBTQ-friendly hotel in West Stockbridge?
Shaker Mill Inn is a top LGBTQ-friendly B&B that features free breakfast and free parking. See all available hotels listed as LGBTQ-friendly in West Stockbridge.
What are some hotels with pools in West Stockbridge?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG are a couple of other choices with an on-site pool. View all hotels with pools in West Stockbridge.
What is staying in West Stockbridge like?
Budget-minded travellers will find good deals in West Stockbridge, and many visitors will definitely appreciate the gardens and restaurants. Tourists can also enjoy so much more including its lake views. In West Stockbridge, there are 33 hotels and other accommodation options to choose from. Find out more about West Stockbridge.
What should I do while I'm visiting West Stockbridge?
Attractions such as Charles H. Baldwin & Sons, Hotchkiss Mobile Studio and Ebenezer II Gifts and Antiques are fun for children of all ages. A couple of additional sights to add to your itinerary are Stockbridge Bowl and Hoffman's Pottery. Take a look at what more there is to see and do in Expedia's West Stockbridge guide.
What's the weather like in West Stockbridge?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in West Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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