Stockbridge Massachusetts Hotels & Motels

Find hotels in Stockbridge using the list and search tools below. Find cheap and discounted hotel/motel rates in or nearby Stockbridge, MA for your upcoming personal or group trip. We list the best Stockbridge, Massachusetts motel and hotel rooms. Browse the Stockbridge area hotels to find the perfect lodging! Please use the provided map of the Stockbridge hotels. Booking 5+ Rooms? Find Stockbridge Group Hotel Discounts

The Stockbridge center point is about 4 miles south of Tanglewood and 9 miles south of Bousquet Ski Area.

Stockbridge, Massachusetts, is a quintessential New England community that perfectly encapsulates the history of the Berkshires. It is located amidst rolling hills and lush landscapes and offers cultural richness, natural beauty, and small-town warmth. Stockbridge's roots date back to the 18th century, and its streets are lined with beautifully preserved buildings that tell tales of a bygone era. Stockbridge is also a hub of culture, home to several renowned attractions. Stroll down Main Street, presenting a peek into classic American heritage. Don't forget to visit the Norman Rockwell Museum to experience the prolific artist's work up close and gain insight into his creative process. The museum's scenic grounds also include walking paths that lead down to the Housatonic River, making it easy to pair art appreciation with outdoor tranquility. Stockbridge also offers a wide range of accommodations to meet every traveler's needs. Visitors can choose from cozy inns, comfortable motels, and elegant hotels, each providing a welcoming atmosphere. Here, you'll find plenty of options to ensure a pleasant stay. Plan your trip today and uncover the stories and landscapes that make Stockbridge a truly special place to explore. More from this guide...

Stockbridge Hotels/Motels & Accommodations

The Red Lion Inn in Stockbridge 30 Main St., Stockbridge, MA 01262 Call
  • 3-star Rural property
  • Hotel has 108 rooms
From£106 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort 190 Meadow St., South Lee, MA 01260 Call ~2.56 miles east of Stockbridge
  • Affordable Mountain hotel
  • Hotel has 334 suites
From£78 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington 980 Pleasant St., Lee, MA 01238 Call ~3.05 miles east of Stockbridge
  • 2-star hotel
  • Free breakfast
From£42 total
Average 3.0 /5 Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge : 42 Stockbridge Rd. 42 Stockbridge Rd., West Stockbridge, MA 01266 Call ~3.33 miles northwest of Stockbridge
  • Two star property
  • Hotel has 16 rooms
From£53 total
Average 3.0 /5 Review Score Call BookMore Details
Applegate Inn - Lee 279 West Park St., Lee, MA 01238 Call ~3.64 miles east of Stockbridge
  • 3 star Rural hotel
  • Hotel has 3 floors
From£141 total
Very good 4.0 /5 Reviews Call BookMore Details
Rodeway Inn - Lee 200 Laurel St., Lee, MA 01238 Call ~3.83 miles northeast of Stockbridge
  • Inexpensive property
  • Check-in time: 11:00
From£53 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Chambery Inn in Lee 199 Main St., Lee, 01238 Call ~3.84 miles east of Stockbridge
  • Three Star property
  • Check in time: 14:00
From£79 total
Very good 4.5 /5 Read Reviews Call BookMore Details
33 Main : 33 Main St. 33 Main St., Lenox, MA 01238 Call ~3.85 miles east of Stockbridge
  • Luxurious Five Star hotel
From£177 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Black Swan Lee Lenox An Ascend Collection Hotel 435 Laurel St., Lee, MA 01238 Call ~3.90 miles northeast of Stockbridge
  • 3-star Lake property
  • Fitness / Gym is on-site
From£53 total
Very good 4.0 /5 Guest Reviews Call BookMore Details
Seven Hills Inn 40 Plunkett St., Lenox, MA 01240 Call ~3.90 miles northeast of Stockbridge
  • Four star Resort property
  • Check in: 3 pm
From£163 total
Very good 4.5 /5 Latest Reviews Call BookMore Details
Wheatleigh in Lenox Hawthorne Rd., Lenox, MA 01240 Call ~4.03 miles north of Stockbridge
  • Affordable property
  • Free breakfast
From£354 total
Very good 4.0 /5 Read Reviews Call BookMore Details
Quality Inn 170 Housatonic St., Lee, MA 01238 Call ~4.07 miles east of Stockbridge
  • 2-star Lake property
  • Check in: 11:00 AM
From£41 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Pilgrim Inn in Lee 165 Housatonic St., Lee, MA 01238 Call ~4.11 miles east of Stockbridge
  • Midscale property
  • Check-in: 3:00 PM
From£70 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Canyon Ranch Lenox in Lenox 165 Kemble St., Lenox, MA 01240 Call ~4.46 miles northeast of Stockbridge
  • 3-star hotel
  • Fitness center on property
From£79 total
Average 3.0 /5 Review Score Call BookMore Details
Apple Tree Inn - Lenox 10 Richmond Mountain Rd., Lenox, MA 01240 Call ~4.58 miles north of Stockbridge
  • 4 star Mountain hotel
  • Check-in time: 4:00 PM
From£88 total
Average 3.0 /5 Review Score Call BookMore Details
Brook Farm Inn 15 Hawthorne St., Lenox, MA 01240 Call ~4.78 miles north of Stockbridge
  • Expensive Rural property
  • 15 rooms in property
From£106 total
Very good 4.0 /5 Read Reviews Call BookMore Details
Kemble Inn 2 Kemble St., Lenox, MA 01240 Call ~5.03 miles northeast of Stockbridge
  • 3-star Mountain hotel
  • Hotel has 12 suites
From£234 total
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Constance by The Lenox Collection 11 Old Stockbridge Rd., Lenox, MA 01240 Call ~5.05 miles north of Stockbridge
  • 4-star property
  • Hotel has 3 floors
From£199 total
Average 3.0 /5 Guest Reviews Call BookMore Details
The Whitlock by The Lenox Collection 16 Church St., Lenox, MA 01240 Call ~5.13 miles northeast of Stockbridge
  • Mid-scale hotel
  • Check-in time: 14:00
From£177 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Great Barrington : 415 Stockbridge Rd. 415 Stockbridge Rd., Great Barrington, MA 01230 Call ~5.23 miles south of Stockbridge
  • Mid-scale Mountain hotel
  • Fitness + Health Center
From£78 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires 400 Stockbridge Rd., Great Barrington, MA 01230 Call ~5.33 miles south of Stockbridge
  • Economical Resort hotel
  • Check-in: 11:00 AM
From£41 total
Average 3.0 /5 Recent Reviews Call BookMore Details
The Dewey by The Lenox Collection 7 Hubbard St., Lenox, MA 01240 Call ~5.57 miles north of Stockbridge
  • Four star hotel
  • Complimentary breakfast is offered
From£66 total
Average 3.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berks - Great Barrington 249 Stockbridge Rd., Great Barrington, MA 01230 Website Call ~5.68 miles south of Stockbridge
  • 3 star Resort hotel
  • Check in: 3:00pm
From£96 total
Very good 4.0 /5 Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires in Lenox 203 Main St., Lenox, MA 01240 Call ~5.79 miles north of Stockbridge
  • Mid-scale Mountain property
  • Free breakfast
From£53 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Eastover Estate & Retreat 430 East St., Lenox, MA 01240 Call ~6.53 miles northeast of Stockbridge
  • Four star Mountain hotel
  • Hotel has 10 meeting rooms
From£96 total
Average 3.5 /5 Guest Reviews Call BookMore Details
Element Lenox Berkshires in Lenox 130 Pittsfield Rd., Lenox, MA 01240 Call ~6.91 miles north of Stockbridge
  • Three Star Mountain property
  • Free breakfast
From£44 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Quality Inn Great Barrington 372 Main St., Great Barrington, MA 01230 Website Call ~6.97 miles south of Stockbridge
  • Two-star Rural hotel
  • Fitness / Gym is on-site
From£88 total
Very good 4.0 /5 Reviews Call BookMore Details
Life House Berkshires 194 Pittsfield Rd., Lenox, MA 01240 Call ~7.23 miles north of Stockbridge
  • 2 star Suburban hotel
  • Check-in time: 2pm
From£43 total
Average 3.0 /5 Review Score Call BookMore Details
Howard Johnson by Wyndham Lenox 462 Pittsfield Rd., Lenox, MA 01240 Call ~7.42 miles north of Stockbridge
  • Economy Resort property
  • Check in time: 2:00 PM
From£57 total
Average 3.0 /5 Read Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only - Lenox 55 Lee Rd., Lenox, MA 01240 Call ~7.99 miles north of Stockbridge
  • High end Resort property
  • 105 rooms in hotel
From£122 total
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites Lenox Berkshires 445 Pittsfield Rd., Lenox, MA 01240 Call ~8.39 miles north of Stockbridge
  • Midscale Mountain property
  • Free comp. breakfast
From£70 total
Average 3.0 /5 Recent Reviews Call BookMore Details
The Yankee Inn in Lenox 461 Pittsfield Rd., Lenox, MA 01240 Call ~8.45 miles north of Stockbridge
  • 2-star hotel
  • 9 suites in property
From£128 total
Very good 4.0 /5 Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center : 802 State Rd. 802 State Rd., Richmond, MA 01254 Call ~8.46 miles north of Stockbridge
  • Affordable Rural property
  • 3 meeting rooms in property
From£132 total
Very good 4.5 /5 Review Score Call BookMore Details
Knights Inn Lenox in Lenox 474 Pittsfield Rd., Lenox, MA 01240 Call ~8.49 miles north of Stockbridge
  • Low Cost Downtown property
  • Hotel has 16 rooms
From£32 total
Poor 2.0 /5 Latest Reviews Call BookMore Details
Lenox Inn in Lenox 525 Pittsfield Rd., Lenox, MA 01240 Call ~8.72 miles north of Stockbridge
  • Cheap hotel
From£53 total
Poor 2.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield 1032 South St., Pittsfield, MA 01201 Call ~8.78 miles north of Stockbridge
  • 3-star Suburban property
  • Hotel has 4 floors
From£84 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires - Pittsfield 1055 South St., Pittsfield, MA 01201 Call ~8.79 miles north of Stockbridge
  • Midscale Suburban property
  • Hotel has 28 suites
From£70 total
Average 3.0 /5 Review Score Call BookMore Details
Berkshire Mountain Lodge 8 Dan Fox Dr., Pittsfield, MA 01201 Call ~9.12 miles north of Stockbridge
  • Low-priced Mountain property
  • Hotel has 146 rooms
From£110 total
Very good 4.5 /5 Read Reviews Call BookMore Details
The Windflower Inn : 684 South Egremont Rd. 684 South Egremont Rd., Great Barrington, MA 01230 Call ~9.43 miles southwest of Stockbridge
  • Mid-scale Mountain hotel
  • 13 rooms in hotel
From£163 total
Excellent 5.0 /5 Recent Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites 1350 West Housatonic St., Pittsfield, MA 01201 Call ~10.13 miles north of Stockbridge
  • 3-star Rural hotel
  • 19 suites in property
From£75 total
Very good 4.5 /5 Reviews Call BookMore Details
Berkshire Inn - Pittsfield 150 West Housatonic St., Pittsfield, MA 01201 Call ~11.21 miles north of Stockbridge
  • 2 star Downtown hotel
  • 2 floors in property
From£79 total
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG 1 West St., Pittsfield, MA 01201 Call ~11.60 miles north of Stockbridge
  • Affordable Downtown hotel
  • Hotel has 170 rooms
From£70 total
Average 3.0 /5 Reviews Call BookMore Details
Hotel on North in Pittsfield 297 North St., Pittsfield, MA 01201 Call ~11.90 miles north of Stockbridge
  • Four star Downtown property
  • Hotel has 4 floors
From£106 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Econo Lodge in Pittsfield 16 Cheshire Rd., Pittsfield, MA 01201 Call ~13.90 miles northeast of Stockbridge
  • Inexpensive Downtown property
  • Check in: 2pm
From£42 total
Poor 2.0 /5 Read Reviews Call BookMore Details
Club Wyndham Bentley Brook - Hancock 1 Corey Rd., Hancock, MA 01237 Call ~18.54 miles north of Stockbridge
  • 3 star Mountain property
  • 152 sleeping rooms in hotel
From£79 total
Very good 4.0 /5 Recent Reviews Call BookMore Details
Jiminy Peak Mountain Resort : 37 Corey Rd. 37 Corey Rd., Hancock, MA 01237 Call ~18.74 miles north of Stockbridge
  • 3 star Mountain hotel
  • Hotel has 3 floors
From£93 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Vacation Village in The Berkshires 276 Brodie Mtn Rd., Lanesborough, MA 01237 Call ~19.49 miles north of Stockbridge
  • Affordable Mountain hotel
  • Hotel has 360 rooms
From£66 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Blackberry River Inn in Norfolk 538 Greenwoods Rd. West, Norfolk, CT 06058 Call ~19.82 miles south of Stockbridge
  • 3 star property
  • Hotel has 17 rooms
From£96 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Manor House Inn in Norfolk 69 Maple Ave., Norfolk, CT 06058 Call ~21.30 miles south of Stockbridge
  • Mid-scale Rural property
  • Hotel has an eco-friendly policy Learn more
From£212 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Wake Robin Inn 106 Sharon Rd., Lakeville, CT 06039 Call ~23.47 miles south of Stockbridge
  • Three Star Rural property
  • 3 conference rooms in property
From£78 total
Average 3.0 /5 Recent Reviews Call BookMore Details

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Prime Seasons to Explore Stockbridge, MA

In Stockbridge, summers are warm, while winters are freezing and snowy. During the year, the temperature typically varies from 15°F to 80°F, so choosing the best time to visit largely depends on the experiences you seek. Spring in Stockbridge is a serene escape as nature awakens with lush greenery and blossoming flowers filling the landscape. This season promises a peaceful retreat perfect for exploring the local historic streets and the nearby Berkshire Botanical Garden. Summer transforms Stockbridge into a lively hub of activities and cultural events. As you stroll along Main Street, you might encounter the Norman Rockwell Museum's captivating exhibits or enjoy a leisurely afternoon around Laurel Lake. During this season, the area comes alive with festivals such as the Tanglewood Music Festival, taking place a short drive away in Lenox. Here, you can indulge in world-class performances set against the backdrop of the stunning Berkshire Hills. Fall is arguably the most picturesque time to visit, as the fall foliage paints the town in brilliant red, orange, and yellow hues. This season provides an idyllic setting for hiking and exploring the area's natural beauty. Local fall festivals, such as those at Berkshire Botanical Garden, celebrate the fall's bounty with crafts, food, and entertainment. Winter in Stockbridge offers a cozy and nostalgic atmosphere. The festive spirit is reflected in holiday decorations and community festivities. Overall, each season in Stockbridge has its own unique appeal, with local festivals enhancing the experience.

Exclusive Hotel Discounts in Stockbridge, MA: The Best Deals for Your Stay

Stockbridge, Massachusetts, is a picturesque town known for its culture and natural beauty. HotelPlanner offers a range of promotions to make this retreat accessible to all. Military discounts honor those who serve, providing a peaceful getaway amidst the town's stunning landscapes. Senior travelers can explore Stockbridge's streets and the renowned Norman Rockwell Museum with the help of senior discounts. Group deals cater to those attending cultural events or embarking on family getaways, ensuring everyone can enjoy the arts and outdoor activities without budget constraints. Long-term discounts are ideal for those who wish to savor the beauty of the Berkshires over an extended stay. HotelPlanner's offers make it easier to indulge in Stockbridge's blend of culture and nature.

Discovering Stockbridge: Exploring New England

Stockbridge has much to offer visitors regarding cultural attractions, stunning nature, and recreational activities. Just outside the downtown area, you'll find Naumkeag, a stunning Gilded Age estate built in 1886 by the Choate family. This property features elegant architecture by Stanford White and innovative landscape design by Fletcher Steele. Visitors can stroll through the iconic "Blue Steps," formal gardens, and sculpture-dotted lawns. Naumkeag hosts events throughout the year, from spring daffodil and tulip festivals to autumn pumpkin shows. For those who love nature, Stockbridge serves as a gateway to the great outdoors. The nearby Berkshire Botanical Garden offers a vast plant collection and peaceful walking paths. It's a relaxing spot to connect with nature. Just a short drive away, Monument Mountain provides scenic hiking trails with breathtaking views of the Berkshire Hills. It's a fantastic excursion at any time of year. With so much to see, Stockbridge has something for everyone. This delightful town invites you to explore its unique attractions and enjoy its natural beauty.

Verified reviews of the city of Stockbridge

Below are reviews of the city of Stockbridge, MA from an actual visitor's perspective.

"Love the city"
Score 4.0 / 5

Love the city, quaint, walkable, historic, beautiful sites.

Karen H., from 18-Apr-2026
"Town is nice as is Lenox nearby"
Score 5.0 / 5

David S., from 17-Oct-2025
"Location"
Score 5.0 / 5

Little shops

Rich C., from 14-Oct-2025
"It’s beautiful and there is so much to see on Main Street. The people are very friendly."
Score 5.0 / 5

Janet D., from 12-Sep-2025
"Good Location"
Score 4.0 / 5

Stockbridge had better access to Tanglewood parking and ability to get out on return to hotel.

David W., from 24-Aug-2025
"The History"
Score 4.0 / 5

The history.

Joann P., from 03-Jan-2025
"Romantic Rooms With Fireplaces"
Score 4.0 / 5

Hot tubs and rooms in season have fake fireplaces that make it romantic in each room.

Cheryl P., from 24-Sep-2024
"The hotel was clean and beds comfortable. "
Score 4.0 / 5

The hotel was clean and beds comfortable. Some nice stores people are polite and friendly the catholic shrine is beautiful.

Richard B., from 18-Apr-2024
"Lovely Town & Shops!"
Score 5.0 / 5

I visited the shops in town and simply enjoyed walking in this lovely town!

Barbara S., from 10-Apr-2023
"Near the National Shrine of The Divine Mercy"
Score 4.0 / 5

We visited the National Shrine of The Divine Mercy and we liked the proximity to it from the hotel.

Dennis F., from 05-Mar-2023
"Rockwell Museum "
Score 5.0 / 5

Enjoyed walking & shopping. Everywhere we ate was delicious. Enjoyed the Rockwell Museum.

Marguerite C., from 13-Nov-2022
"Quaint Little Place & Shops to Wander Into!"
Score 5.0 / 5

It's a quaint little place to wander into all the shops.

Gwenn B., from 07-Nov-2022
"Great Location Near Attractions"
Score 4.0 / 5

Walkable to restaurants and shops. Quick drive to many attractions like Naumkeag, the Mount, Tanglewood, etc.

Paula S., from 15-Sep-2022
"Quaint!"
Score 4.0 / 5

The quaintness of the town echoing a time gone by coupled with an array and blend of history and a plethora of artsy things to do.

Richard S., from 14-Jun-2022
"Loved the Norman Rockwell Museum, the Quaint Downtown & Food!"
Score 4.0 / 5

Quaint downtown. Good food and loved the Norman Rockwell Museum which was about a 5 to 10 minute drive from hotel.

Roy S., from 24-Apr-2022
"Family Friendly"
Score 4.0 / 5

Quiet, simple living. I think people know each other well within the community.

Ludina F., from 13-Apr-2015
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