Photo by William Keller

Hotels in Stockbridge

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Tonight
Feb 9 - Feb 10
Tomorrow
Feb 10 - Feb 11
This weekend
Feb 13 - Feb 15
Next weekend
Feb 20 - Feb 22

Where to stay in Stockbridge?

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, (110 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
Feb 22 - Feb 23
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior
The Red Lion Inn
The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
The price is $155
$218 total
includes taxes & fees
Mar 12 - Mar 13
The Red Lion Inn
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 $239
$280 total
includes taxes & fees
Feb 22 - Feb 23
The Inn at Stockbridge
Exterior
The Little Lion
The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (553 reviews)
Experience comfort and convenience at this motel in Great Barrington, where free WiFi and parking await. Explore nearby Monument Mountain Reservation for hiking, then return to spotless rooms with daily housekeeping and notably helpful staff.
The price is $110
$123 total
includes taxes & fees
Feb 10 - Feb 11
The Little Lion
Room #10 Queen's Cottage | Living room | Flat-screen TV
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (135 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
Feb 10 - Feb 11
Devonfield Inn B&B
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, (1,001 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 $65
$71 total
includes taxes & fees
Feb 10 - Feb 11
Pleasant Valley Motel West Stockbridge
Front of property
Chambery Inn
Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374 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
Feb 10 - Feb 11
Chambery Inn
Porch
Lakehouse Inn
Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (292 reviews)
Immerse yourself in tranquility at this waterfront B&B offering complimentary perks including daily full breakfast and parking. Explore the lake with onsite kayaking or unwind on the terrace before visiting nearby Wyndhurst Golf & Club and The Mount.
The price is $144
$169 total
includes taxes & fees
Feb 27 - Feb 28
Lakehouse Inn
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (445 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 $110
$121 total
includes taxes & fees
Feb 10 - Feb 11
Shaker Mill Inn
In-room safe, desk, free cribs/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, (567 reviews)
The price is $75
$84 total
includes taxes & fees
Feb 10 - Feb 11
Travelodge by Wyndham Great Barrington Berkshires
Seasonal outdoor pool
Sunset Inn
Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 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 $95
$106 total
includes taxes & fees
Feb 10 - Feb 11
Sunset Inn
In-room dining
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (658 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
Feb 22 - Feb 23
Econo Lodge Lee - Great Barrington
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
9.0 out of 10, Wonderful, (833 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 $113
$145 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Individually decorated, individually furnished, desk, laptop workspace
Granville House
Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (94 reviews)
This charming business-friendly B&B offers free full breakfast, WiFi, and parking in scenic Housatonic. Explore nearby Monument Mountain and its reservation, with Pittsfield Municipal Airport just a 28-minute drive away.
The price is $174
$194 total
includes taxes & fees
Feb 10 - Feb 11
Granville House
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, (1,004 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 $98
$109 total
includes taxes & fees
Mar 1 - Mar 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Individually decorated, individually furnished, desk, laptop workspace
Pilgrim Inn
Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (332 reviews)
Embrace the charm of this Lee golf-side retreat with free WiFi and self parking. Located near Lee Library and Animagic Museum, this cozy inn provides convenient 24-hour front desk service while winter enthusiasts can enjoy nearby cross-country skiing.
The price is $80
$89 total
includes taxes & fees
Feb 10 - Feb 11
Pilgrim Inn
Front of property
Brook Farm Inn
Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
Immerse yourself in Lenox charm at this B&B featuring outdoor and poolside bars, just minutes from Shakespeare and Company. Enjoy complimentary breakfast, WiFi, and parking while the attentive staff ensures a memorable stay.
The price is $187
$217 total
includes taxes & fees
Feb 16 - Feb 17
Brook Farm Inn
Lobby
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 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 $84
$94 total
includes taxes & fees
Feb 22 - Feb 23
Quality Inn Lee - Lenox South
Exterior
The Whitlock
The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (286 reviews)
Immerse yourself in the Berkshires at this charming hotel just 5 minutes from Tanglewood Music Center. Enjoy hiking trails nearby, plus free WiFi and parking. A terrace, garden and helpful staff create a welcoming atmosphere for music lovers and nature enthusiasts alike.
The price is $128
$143 total
includes taxes & fees
Feb 10 - Feb 11
The Whitlock
Exterior
33 Main
33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
Experience the charm of 33 Main in Lenox, a cozy B&B offering full breakfast from 8:30-10:00 AM. Located near Lenox Library and The Bookstore, this hotel includes free WiFi and parking for exploring Berkshires culture.
The price is $410
$458 total
includes taxes & fees
Feb 23 - Feb 24
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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When is the best time to visit Stockbridge?

Our prices for hotels in Stockbridge are cheapest in April
Price trends for hotels in Stockbridge
Pricing is based on two traveler single night rates
View properties in February
Currently viewing crowd sizes and weather for February.
Typical weather for Stockbridge
February
High 0°C / low -8°C. Snow likely.
View properties in February
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Top landmarks in Stockbridge

Norman Rockwell Museum

4.7/5 (252 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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National Shrine of the Divine Mercy

4.5/5 (54 reviews)
If seeing the sights is on your list of things to do, head to National Shrine of the Divine Mercy— just one of the landmarks located 0.5 mi (0.8 km) from central Stockbridge.
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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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Linwood House at the Norman Rockwell Museum Stockbridge Massachusetts USA. Significant collection of the artist's original work & memorabilia on display in his hometown.
Photo by William Keller
Open Photo by William Keller

Check out reviews of Stockbridge hotels guests love

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Only stayed for 1 night but was very impressed with this property. The room was very clean and spacious. Bed was comfortable as well. Had my two kids with me so the pool and hot tub was an amazing amenity. Left early in the morning to ski so the stay was short, but would’ve loved to stay longer and will definitely look to return to this property in the future. "
Gregory 1-night trip
Posted 4 days ago
Berkshire Mountain Lodge

Frequently asked questions

What hotels do travelers like in Stockbridge?
The Red Lion Inn is a property that our guests really like.
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 29 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.