Hotels in West Stockbridge

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Next weekend
May 22 - May 24
In two weeks
May 29 - May 31

Where to stay in West Stockbridge?

Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
Escape to the heart of the Berkshires in this well-maintained motel close to Tanglewood Music Center. Free WiFi and parking make exploring local attractions like Hoffman's Pottery and Charles H. Baldwin & Sons effortless. Clean rooms and daily housekeeping ensure a comfortable stay.
The price is $70
$77 total
includes taxes & fees
May 26 - May 27
Pleasant Valley Motel West Stockbridge
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (454 reviews)
Experience tranquility at this West Stockbridge B&B where hiking, biking, and kayaking adventures await. Enjoy free breakfast, complimentary parking, and daily housekeeping while exploring Ebenezer II Gifts and nearby cultural attractions.
The price is $112
$123 total
includes taxes & fees
May 25 - May 26
Shaker Mill Inn
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
Tucked away in Becket, this motel offers convenient perks like free WiFi, complimentary parking, and room service. Hiking enthusiasts can explore nearby trails and visit the historic Becket Land Trust Quarry for outdoor adventures.
The price is $95
$140 total
includes taxes & fees
May 31 - Jun 1
Becket Motel
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (178 reviews)
Unwind in this peaceful country retreat with a seasonal outdoor pool and complimentary gourmet breakfast. Located near Haystack Mountain State Park, the inn offers free WiFi and parking while helpful staff ensure a memorable stay in Norfolk's quiet surroundings.
The price is $156
$179 total
includes taxes & fees
May 17 - May 18
Blackberry River Inn
Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (137 reviews)
Unwind at this charming Great Barrington retreat featuring complimentary breakfast, WiFi, and parking. The hotel offers a restaurant, welcoming bar, and tranquil outdoor spaces near Questing and New Marlborough Town Library.
The price is $175
$192 total
includes taxes & fees
May 17 - May 18
Gedney Farm
Thayer House, Room 205, 1 King bed | Premium bedding, individually decorated, individually furnished

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
Experience culinary delights at The Old Inn Fine Dining, featuring American cuisine for breakfast, lunch, and dinner. Cool off in the seasonal pool, then sip drinks at the bar. Nearby attractions Questing and New Marlborough Town Library await your exploration.
The price is $330
$398 total
includes taxes & fees
May 17 - May 18
The Old Inn On The Green
Comfort Room, Private Bathroom (Rolling Meadows) | Individually decorated, individually furnished, free WiFi, bed sheets

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
This charming B&B offers free breakfast, WiFi, and parking in scenic Cheshire. Explore nearby attractions like Adams Theater and Mount Greylock State Reservation, then return to this welcoming inn. Pittsfield Station is just a 16-minute drive away.
The price is $254
$268 total
includes taxes & fees
May 18 - May 19
Harbour House Inn
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
Wake up to a complimentary full breakfast at this cozy East Canaan B&B. Located near Land of Nod Vineyard and Winery, the inn offers free parking and daily housekeeping. Guests consistently praise the helpful staff for making stays memorable.
The price is $105
$121 total
includes taxes & fees
May 17 - May 18
Locust Tree Bed and Breakfast LLC
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
This peaceful Lee hotel offers free daily continental breakfast near local restaurants and shopping. Just minutes from Lee Library and Animagic Museum, guests praise the helpful staff. Enjoy convenient access to cultural attractions during your Berkshires stay.
The price is $113
$126 total
includes taxes & fees
Jun 15 - Jun 16
Quality Inn Lee - Lenox South
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (412 reviews)
Nestled in Lee, this motel offers easy access to Tanglewood Music Center, along with free WiFi and parking. Cool off in the seasonal outdoor pool after exploring nearby trails, or venture to Lee Library and Animagic Museum of Animation.
The price is $110
$123 total
includes taxes & fees
May 26 - May 27
Sunset Inn
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (819 reviews)
Tucked away in a peaceful corner of Pittsfield, this quiet motel offers free WiFi and parking with a 24-hour front desk. Nearby Crane Museum of Papermaking awaits exploration, while winter enthusiasts will love the downhill skiing options just moments away.
The price is $79
$88 total
includes taxes & fees
May 17 - May 18
FairBridge Inn Express
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
This serene B&B in Lee offers tranquil accommodations where quiet is the hallmark. Unwind with deep-tissue massages or aromatherapy after exploring nearby attractions. The terrace, hot tub, and snack bar create a rejuvenating escape in the Berkshires.
The price is $190
$212 total
includes taxes & fees
May 17 - May 18
Chambery Inn
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (663 reviews)
This Lee motel offers a playful mini golf course on-site and free continental breakfast to start your day. Located near Greenock Country Club and Lee Premium Outlets, guests praise the helpful staff. Enjoy complimentary WiFi and parking during your stay.
The price is $68
$75 total
includes taxes & fees
May 25 - May 26
Econo Lodge Lee - Great Barrington
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
Surrounded by the Berkshires, this B&B offers a peaceful outdoor pool and soothing massages after a day on the adjacent golf course. Free breakfast, Wi-Fi, and parking enhance your stay near Greenock Country Club and local attractions.
The price is $269
$300 total
includes taxes & fees
May 18 - May 19
Devonfield Inn B&B
Lake

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, (1,000 reviews)
This peaceful Lenox hotel overlooks a picturesque lake where spectacular sunsets unfold daily. Enjoy Indian cuisine at Mint restaurant, complimentary breakfast, and free WiFi. Just 10 minutes from Tanglewood Music Center with convenient parking.
The price is $121
$135 total
includes taxes & fees
May 27 - May 28
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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
3.5 star property
South Lee
9.2 out of 10, Wonderful, (895 reviews)
Nestled in South Lee, this family-friendly retreat features 4 pools total - 2 indoor and 2 outdoor, including a seasonal option. Enjoy refreshments at the pool bar or coffee shop after exploring nearby Tanglewood Music Center and Berkshire attractions.
The price is $116
$149 total
includes taxes & fees
May 18 - May 19
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
This cozy B&B offers a tranquil escape with an outdoor pool and massage services. Just minutes from National Shrine of the Divine Mercy and Berkshire Theatre Festival, guests enjoy free breakfast, WiFi, and parking while exploring the scenic area.
The price is $263
$308 total
includes taxes & fees
May 21 - May 22
The Inn at Stockbridge
Indoor pool

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, (94 reviews)
Escape to the heart of Pittsfield where this hotel offers an indoor pool and relaxing hot tub after exploring Tanglewood. Free breakfast, WiFi, and parking enhance your stay while nearby Guido's Marketplace awaits your discovery.
The price is $127
$142 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (677 reviews)
Embrace comfort at this Pittsfield retreat with an indoor pool and fitness center. Jae's Asian Fusion restaurant serves three daily meals, while rooms offer convenient refrigerators and microwaves. Guido's Marketplace and literary landmarks await nearby.
The price is $132
$147 total
includes taxes & fees
May 25 - May 26
Hilton Garden Inn Lenox Pittsfield
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, (853 reviews)
Dive into Berkshires charm at this centrally located Lenox motel, where you'll enjoy the refreshing outdoor pool and free parking. Near Guido's Marketplace and Bousquet Ski Area, with clean rooms and exceptionally helpful staff to enhance your stay.
The price is $79
$88 total
includes taxes & fees
May 17 - May 18
Howard Johnson by Wyndham Lenox
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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When is the best time to visit West Stockbridge?

Our prices for hotels in West Stockbridge are cheapest in December
Price trends for hotels in West Stockbridge
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for West Stockbridge
May
High 19°C / low 8°C. Sunny most days.
View properties in May
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May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 14 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 7 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 2 degrees Celsius, average low temperature -5 degrees Celsius. Snow likely.
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January, no crowd data, average high temperature -2 degrees Celsius, average low temperature -9 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 0 degrees Celsius, average low temperature -8 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 5 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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April, no crowd data, average high temperature 12 degrees Celsius, average low temperature 2 degrees Celsius. Cloudy most days.
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Monthly weather averages (˚C)

Top landmarks in West Stockbridge

Charles H. Baldwin & Sons

Charles H. Baldwin & Sons is in the heart of West Stockbridge, so why not stop by during your stay. If you have fun at Charles H. Baldwin & Sons, you'll love Hotchkiss Mobile Studio and Ebenezer II Gifts and Antiques, both a short walk away.
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Learn more about West Stockbridge

Notable for its gardens, West Stockbridge features attractions such as Stockbridge Bowl and Charles H. Baldwin & Sons. The city has something for everyone including restaurants along with sights like Hotchkiss Mobile Studio and Ebenezer II Gifts and Antiques.

See all hotels in West Stockbridge
Olivias Overlook - West Stockbridge, Massachusetts

Check out reviews of West Stockbridge hotels guests love

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Over the top customer service. Comfortable, super clean room. "
Ann 1-night trip
Posted 8 hours ago
The Yankee Inn

Frequently asked questions

What accommodations do travelers recommend in West Stockbridge?
Guests like Shaker Mill Inn, Berkshire Mountain Lodge and Berkshires Untold.
Can I book refundable accommodations in West Stockbridge?
If you want the flexibility to change your travel plans to West Stockbridge, most accommodations offer refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in West Stockbridge if I want a vacation home instead of a hotel?
If you want a good alternative to a hotel, browse our selection of 20 vacation homes. You can also book one of the 5 cabins for your stay.
What will the weather in West Stockbridge be like during my trip?
July and August are typically the warmest months in West Stockbridge when the average temp is 66°F. January and February are the coldest months when the average temperature is 27°F. October and July are the months with the most rain.
Why should I book my West Stockbridge hotel with Hotels.com?
There are lots of reasons to book your West Stockbridge trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.