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 : 30 Main St. 30 Main St., Stockbridge, MA 01262 Call
  • Affordable Rural hotel
  • 4 floors in property
From$80
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort in South Lee 190 Meadow St., South Lee, MA 01260 Call ~2.56 miles east of Stockbridge
  • Midscale Mountain hotel
  • Check-in time: 4:00pm
From$89
Very Good 4.0 /5 Read 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
  • 28 rooms in hotel
From$48
Average 3.0 /5 Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge 42 Stockbridge Rd., West Stockbridge, MA 01266 Call ~3.33 miles northwest of Stockbridge
  • Inexpensive hotel
  • Check-in: 13:00
From$60
Average 3.0 /5 Read Reviews Call BookMore Details
Applegate Inn in Lee 279 West Park St., Lee, MA 01238 Call ~3.64 miles east of Stockbridge
  • Affordable Rural property
  • 6 suites in hotel
From$160
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Rodeway Inn - Lee 200 Laurel St., Lee, MA 01238 Call ~3.83 miles northeast of Stockbridge
  • 2 star hotel
  • Hotel has 23 rooms
From$60
Average 3.0 /5 Read Reviews Call BookMore Details
Chambery Inn : 199 Main St. 199 Main St., Lee, 01238 Call ~3.84 miles east of Stockbridge
  • Three Star hotel
  • Check-in time: 14:00
From$90
Very Good 4.5 /5 Guest Reviews Call BookMore Details
33 Main - Lenox 33 Main St., Lenox, MA 01238 Call ~3.85 miles east of Stockbridge
  • Luxury Five Star property
From$200
Average 3.0 /5 Review Score Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel in Lee 435 Laurel St., Lee, MA 01238 Call ~3.90 miles northeast of Stockbridge
  • Affordable Lake property
  • Check-in: 3:00PM
From$60
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Seven Hills Inn 40 Plunkett St., Lenox, MA 01240 Call ~3.90 miles northeast of Stockbridge
  • Expensive Resort hotel
  • 4 suites in property
From$184
Very Good 4.5 /5 Reviews Call BookMore Details
Quality Inn : 435 Laurel St. 435 Laurel St., Lee, MA 01238 Website Call ~3.91 miles northeast of Stockbridge
  • 3 star Lake hotel
  • 52 rooms in property
From$65
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Wheatleigh Hawthorne Rd., Lenox, MA 01240 Call ~4.03 miles north of Stockbridge
  • Midscale hotel
  • Hotel has 9 suites
From$400
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Pilgrim Inn - Lee 165 Housatonic St., Lee, MA 01238 Call ~4.11 miles east of Stockbridge
  • Mid-scale property
From$80
Average 3.0 /5 Reviews Call BookMore Details
Canyon Ranch Lenox 165 Kemble St., Lenox, MA 01240 Call ~4.46 miles northeast of Stockbridge
  • Affordable hotel
  • 2 floors in property
From$90
Average 3.0 /5 Recent Reviews Call BookMore Details
Apple Tree Inn : 10 Richmond Mountain Rd. 10 Richmond Mountain Rd., Lenox, MA 01240 Call ~4.58 miles north of Stockbridge
  • High end Mountain property
  • 3 floors in hotel
From$100
Average 3.0 /5 Read Reviews Call BookMore Details
Brook Farm Inn in Lenox 15 Hawthorne St., Lenox, MA 01240 Call ~4.78 miles north of Stockbridge
  • High end Rural hotel
  • 3 floors in property
From$120
Very Good 4.0 /5 Recent 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 a green policy Learn more
From$265
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$225
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
  • 3-star property
  • 2 floors in hotel
From$200
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express Great Barrington 415 Stockbridge Rd., Great Barrington, MA 01230 Call ~5.23 miles south of Stockbridge
  • 3-star Mountain property
  • Hotel has an eco-friendly policy Read more
From$89
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires 400 Stockbridge Rd., Great Barrington, MA 01230 Call ~5.33 miles south of Stockbridge
  • Economy Resort hotel
  • Check in: 11:00 AM
From$47
Average 3.0 /5 Latest Reviews Call BookMore Details
The Dewey by The Lenox Collection 7 Hubbard St., Lenox, MA 01240 Call ~5.57 miles north of Stockbridge
  • High end property
  • 12 rooms in property
From$75
Average 3.0 /5 Hotel Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi in Great Barrington 249 Stockbridge Rd., Great Barrington, MA 01230 Website Call ~5.68 miles south of Stockbridge
  • Mid-scale Resort hotel
  • Gym is available on property
From$109
Very Good 4.0 /5 Guest Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires 203 Main St., Lenox, MA 01240 Call ~5.79 miles north of Stockbridge
  • Midscale Mountain property
  • Free breakfast
From$60
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Eastover Estate & Retreat 430 East St., Lenox, MA 01240 Call ~6.53 miles northeast of Stockbridge
  • High end Mountain hotel
  • 2 floors in hotel
From$109
Average 3.5 /5 Reviews Call BookMore Details
Element Lenox Berkshires 130 Pittsfield Rd., Lenox, MA 01240 Call ~6.91 miles north of Stockbridge
  • Affordable Mountain hotel
  • 118 rooms in property
From$50
Average 3.0 /5 Review Score Call BookMore Details
Quality Inn Great Barrington 372 Main St., Great Barrington, MA 01230 Website Call ~6.97 miles south of Stockbridge
  • Cheap Rural hotel
  • 63 rooms in hotel
From$100
Very Good 4.0 /5 Read Reviews Call BookMore Details
Life House Berkshires : 194 Pittsfield Rd. 194 Pittsfield Rd., Lenox, MA 01240 Call ~7.23 miles north of Stockbridge
  • Economical Suburban hotel
  • Check in time: 2pm
From$49
Average 3.0 /5 Guest Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox - Lenox 462 Pittsfield Rd., Lenox, MA 01240 Call ~7.42 miles north of Stockbridge
  • Low priced Resort property
  • 2 floors in hotel
From$65
Average 3.0 /5 Hotel Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only 55 Lee Rd., Lenox, MA 01240 Call ~7.99 miles north of Stockbridge
  • Four-star Resort property
  • Check-in time: 3PM
From$138
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox 445 Pittsfield Rd., Lenox, MA 01240 Call ~8.39 miles north of Stockbridge
  • 3-star Mountain hotel
  • 24 suites in hotel
From$109
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Yankee, Trademark Collection by Wyndham in Lenox 461 Pittsfield Rd., Lenox, MA 01240 Call ~8.45 miles north of Stockbridge
  • Low Cost hotel
  • Free comp. breakfast
From$145
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center - Richmond 802 State Rd., Richmond, MA 01254 Call ~8.46 miles north of Stockbridge
  • Affordable Rural property
  • 3 conference rooms in property
From$150
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Knights Inn Lenox in Lenox 474 Pittsfield Rd., Lenox, MA 01240 Call ~8.49 miles north of Stockbridge
  • Low-priced Downtown hotel
  • 16 rooms in hotel
From$37
Poor 2.0 /5 Reviews Call BookMore Details
Lenox Inn in Lenox 525 Pittsfield Rd., Lenox, MA 01240 Call ~8.72 miles north of Stockbridge
  • Cheap hotel
  • 18 rooms in property
From$60
Poor 2.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield - Pittsfield 1032 South St., Pittsfield, MA 01201 Call ~8.78 miles north of Stockbridge
  • Mid-scale Suburban property
  • Fitness center on property
From$95
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires 1055 South St., Pittsfield, MA 01201 Call ~8.79 miles north of Stockbridge
  • Affordable Suburban property
  • Check-in: 3pm
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Berkshire Mountain Lodge 8 Dan Fox Dr., Pittsfield, MA 01201 Call ~9.12 miles north of Stockbridge
  • 2 star Mountain hotel
  • 2 meeting rooms in hotel
From$125
Very Good 4.5 /5 Reviews Call BookMore Details
The Windflower Inn 684 South Egremont Rd., Great Barrington, MA 01230 Call ~9.43 miles southwest of Stockbridge
  • 3 star Mountain property
  • Free breakfast
From$185
Excellent 5.0 /5 Guest 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
  • Affordable Rural property
  • Hotel has 59 rooms
From$85
Very Good 4.5 /5 Review Score Call BookMore Details
Berkshire Inn : 150 West Housatonic St. 150 West Housatonic St., Pittsfield, MA 01201 Call ~11.21 miles north of Stockbridge
  • Economical Downtown hotel
  • 2 floors in hotel
From$90
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG : 1 West St. 1 West St., Pittsfield, MA 01201 Call ~11.60 miles north of Stockbridge
  • 3 star Downtown hotel
  • Hotel has 170 rooms
From$80
Average 3.0 /5 Review Score Call BookMore Details
Hotel on North in Pittsfield 297 North St., Pittsfield, MA 01201 Call ~11.92 miles north of Stockbridge
  • Four-star Downtown property
  • 4 floors in hotel
From$150
Excellent 5.0 /5 Read Reviews Call BookMore Details
Econo Lodge in Pittsfield 16 Cheshire Rd., Pittsfield, MA 01201 Call ~13.90 miles northeast of Stockbridge
  • Low priced Downtown hotel
  • Hotel has 2 floors
Club Wyndham Bentley Brook : 1 Corey Rd. 1 Corey Rd., Hancock, MA 01237 Call ~18.54 miles north of Stockbridge
  • 3-star Mountain hotel
  • Hotel has 4 floors
From$90
Very Good 4.0 /5 Review Score Call BookMore Details
Jiminy Peak Mountain Resort - Hancock 37 Corey Rd., Hancock, MA 01237 Call ~18.74 miles north of Stockbridge
  • Affordable Mountain hotel
  • Hotel has 102 rooms
From$105
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Vacation Village in The Berkshires : 276 Brodie Mtn Rd. 276 Brodie Mtn Rd., Lanesborough, MA 01237 Call ~19.49 miles north of Stockbridge
  • 3 star Mountain property
  • 360 suites in hotel
From$75
Very Good 4.0 /5 Review Score Call BookMore Details
Blackberry River Inn 538 Greenwoods Rd. West, Norfolk, CT 06058 Call ~19.82 miles south of Stockbridge
  • 3 star hotel
  • Check in time: 15:00
From$109
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Manor House Inn - Norfolk 69 Maple Ave., Norfolk, CT 06058 Call ~21.30 miles south of Stockbridge
  • Affordable Rural hotel
  • Hotel has 3 floors
From$240
Very Good 4.0 /5 Read Reviews Call BookMore Details
Wake Robin Inn in Lakeville 106 Sharon Rd., Lakeville, CT 06039 Call ~23.47 miles south of Stockbridge
  • Mid-scale Rural hotel
  • Comp. Breakfast
From$89
Average 3.0 /5 Hotel 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.

"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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