Hotels in Stockbridge

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Check prices for these dates

Tonight
May 11 - May 12
Tomorrow
May 12 - May 13
This weekend
May 15 - May 17
Next weekend
May 22 - May 24

Where to stay in Stockbridge?

Exterior
The Red Lion Inn
The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,010 reviews)
The price is $174
$239 total
includes taxes & fees
May 18 - May 19
The Red Lion Inn
Suite, Private Bathroom (RedBird Suite) | View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (111 reviews)
This historic Stockbridge inn offers free breakfast and WiFi plus a seasonal outdoor pool and garden terrace. Enjoy hiking trails, horseback riding, and kayaking on-site while Tanglewood Music Center awaits just a short drive away.
The price is $309
$374 total
includes taxes & fees
May 25 - May 26
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 21 - May 22
Becket Motel
Library
Blackberry River Inn
Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (177 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 12 - May 13
Blackberry River Inn
Front of property
Gedney Farm
Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (136 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 18 - May 19
Gedney Farm
Breakfast, lunch, dinner served; American cuisine
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 12 - May 13
The Old Inn On The Green
Exterior
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 14 - May 15
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 12 - May 13
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, (1,004 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 1 - Jun 2
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 $99
$111 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 12 - May 13
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 12 - May 13
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 $64
$71 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, (137 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 12 - May 13
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, (1,008 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 $117
$131 total
includes taxes & fees
May 19 - May 20
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, (892 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 $128
$162 total
includes taxes & fees
May 13 - May 14
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, (93 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 $106
$119 total
includes taxes & fees
May 17 - May 18
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 $127
$141 total
includes taxes & fees
May 17 - May 18
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 13 - May 14
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 Stockbridge?

Our prices for hotels in Stockbridge are cheapest in May
Price trends for hotels in 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 Stockbridge
May
High 19°C / low 8°C. Sunny most days.
View properties in May
19°
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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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23°
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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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27°
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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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26°
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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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22°
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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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14°
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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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12°
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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 Stockbridge

Norman Rockwell Museum

4.7/5 (347 reviews)
Norman Rockwell Museum is 0.8 mi (1.2 km) from central Stockbridge, why not stop by during your stay. If you want to experience more of the culture Stockbridge has to offer, head to Berkshire Botanical Garden, Naumkeag Museum, and National Shrine of the Divine Mercy.
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Learn more about Stockbridge

Wander through Norman Rockwell's America at his museum, where small-town life springs from canvas to memory. The red-brick Main Street looks suspiciously like his famous Christmas painting because, well, it is. Summer brings world-class music when Tanglewood hosts the Boston Symphony Orchestra in nearby Lenox. History buffs can explore the Mission House and Naumkeag's elegant gardens with their curious blue stairs. The Berkshire Botanical Garden offers seasonal splendor without the crowds of bigger attractions. For a perfect afternoon, grab a coffee on Main Street before heading to the Housatonic River, where locals fish in spots they'll reluctantly share if asked nicely.

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Vivid autumn foliage reflected in a calm lake surrounded by a dense forest under a clear blue sky in Stockbridge, Massachusetts

Check out reviews of Stockbridge hotels guests love

Hotel On North

Hotel On North

10/10 Excellent
"It was an absolute pleasure to stay! We enjoyed ourselves and felt very comfortable"
philip 1-night trip
Posted 2 hours ago
Hotel On North

Frequently asked questions

What hotels do travelers like in Stockbridge?
Guests like The Red Lion Inn, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood and Berkshire Mountain Lodge.
Can I book refundable hotels in Stockbridge?
If you want the flexibility to change your plans to Stockbridge, most accommodations offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Stockbridge if I want a vacation home instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 32 vacation homes. You can also consider one of the 8 cottages for your trip.
What will the weather in Stockbridge be like during my vacation?
The warmest months in Stockbridge are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 27°F. The rainiest months are October and July.
Why should I book my Stockbridge hotel with Hotels.com?
There are plenty of reasons to book your Stockbridge travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, 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.