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
+1-888-389-4121
30 Main St., Stockbridge, MA 01262 +1-888-389-4121
  • Mid-scale Rural hotel
  • 8 meeting rooms in property
From£58
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort
+1-888-675-2083
190 Meadow St., South Lee, MA 01260 +1-888-675-2083 ~2.56 miles east of Stockbridge
  • Midscale Mountain property
  • Fitness / Gym is on-site
From£65
Very good 4.0 /5 Guest Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington : 980 Pleasant St.
+1-800-716-8490
980 Pleasant St., Lee, MA 01238 +1-800-716-8490 ~3.05 miles east of Stockbridge
  • Economy property
  • Check-in: 11:00
From£35
Average 3.0 /5 Review Score Call BookMore Details
Pleasant Valley Motel West Stockbridge
+1-800-805-5223
42 Stockbridge Rd., West Stockbridge, MA 01266 +1-800-805-5223 ~3.33 miles northwest of Stockbridge
  • Economical hotel
  • 16 rooms in property
From£43
Average 3.0 /5 Guest Reviews Call BookMore Details
Applegate Inn
+1-888-965-1860
279 West Park St., Lee, MA 01238 +1-888-965-1860 ~3.64 miles east of Stockbridge
  • 3-star Rural hotel
  • Free breakfast
From£117
Very good 4.0 /5 Guest Reviews Call BookMore Details
Rodeway Inn
+1-888-788-5576
200 Laurel St., Lee, MA 01238 +1-888-788-5576 ~3.83 miles northeast of Stockbridge
  • 2 star property
  • 23 rooms in property
From£43
Average 3.0 /5 Read Reviews Call BookMore Details
Chambery Inn : 199 Main St.
+1-888-897-9207
199 Main St., Lee, 01238 +1-888-897-9207 ~3.84 miles east of Stockbridge
  • 3-star property
  • Check in time: 14:00
From£65
Very good 4.5 /5 Read Reviews Call BookMore Details
33 Main in Lenox
+1-888-311-4278
33 Main St., Lenox, MA 01238 +1-888-311-4278 ~3.85 miles east of Stockbridge
  • Luxury 5-star hotel
From£146
Average 3.0 /5 Reviews Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel : 435 Laurel St.
+1-888-469-4795
435 Laurel St., Lee, MA 01238 +1-888-469-4795 ~3.90 miles northeast of Stockbridge
  • Mid-scale Lake hotel
  • Fitness / Gym is on-site
From£43
Very good 4.0 /5 Latest Reviews Call BookMore Details
Seven Hills Inn : 40 Plunkett St.
+1-888-734-9421
40 Plunkett St., Lenox, MA 01240 +1-888-734-9421 ~3.90 miles northeast of Stockbridge
  • 4-star Resort property
  • 2 floors in property
From£134
Very good 4.5 /5 Review Score Call BookMore Details
Quality Inn - Lee
+1-888-841-5292
435 Laurel St., Lee, MA 01238 Website +1-888-841-5292 ~3.91 miles northeast of Stockbridge
  • Mid-scale Lake hotel
  • Check-in: 3:00 PM
From£47
Very good 4.0 /5 Reviews Call BookMore Details
Wheatleigh in Lenox
+1-888-455-5160
Hawthorne Rd., Lenox, MA 01240 +1-888-455-5160 ~4.03 miles north of Stockbridge
  • Midscale hotel
  • Check in: 16:00
From£293
Very good 4.0 /5 Recent Reviews Call BookMore Details
Pilgrim Inn in Lee
+1-888-965-8297
165 Housatonic St., Lee, MA 01238 +1-888-965-8297 ~4.11 miles east of Stockbridge
  • 3 star property
From£58
Average 3.0 /5 Hotel Reviews Call BookMore Details
Canyon Ranch Lenox in Lenox
+1-888-906-6358
165 Kemble St., Lenox, MA 01240 +1-888-906-6358 ~4.46 miles northeast of Stockbridge
  • 3 star hotel
  • 2 floors in hotel
From£65
Average 3.0 /5 Recent Reviews Call BookMore Details
Apple Tree Inn : 10 Richmond Mountain Rd.
+1-888-749-6785
10 Richmond Mountain Rd., Lenox, MA 01240 +1-888-749-6785 ~4.58 miles north of Stockbridge
  • Expensive Mountain hotel
  • 3 floors in property
From£73
Average 3.0 /5 Latest Reviews Call BookMore Details
Brook Farm Inn - Lenox
+1-888-878-9982
15 Hawthorne St., Lenox, MA 01240 +1-888-878-9982 ~4.78 miles north of Stockbridge
  • High-end Rural hotel
  • Has environment-friendly policy See more
From£87
Very good 4.0 /5 Latest Reviews Call BookMore Details
Kemble Inn - Lenox
+1-888-389-4485
2 Kemble St., Lenox, MA 01240 +1-888-389-4485 ~5.03 miles northeast of Stockbridge
  • Mid-scale Mountain property
  • Hotel has 3 meeting rooms
From£194
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Constance by The Lenox Collection - Lenox
+1-888-389-4121
11 Old Stockbridge Rd., Lenox, MA 01240 +1-888-389-4121 ~5.05 miles north of Stockbridge
  • 4 star hotel
  • Free breakfast available
From£164
Average 3.0 /5 Guest Reviews Call BookMore Details
The Whitlock by The Lenox Collection : 16 Church St.
+1-888-675-2083
16 Church St., Lenox, MA 01240 +1-888-675-2083 ~5.13 miles northeast of Stockbridge
  • 3 star hotel
  • 30 rooms in property
From£146
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Great Barrington : 415 Stockbridge Rd.
+1-800-716-8490
415 Stockbridge Rd., Great Barrington, MA 01230 +1-800-716-8490 ~5.23 miles south of Stockbridge
  • 3 star Mountain property
  • Hotel has 78 rooms
From£65
Very good 4.0 /5 Recent Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires : 400 Stockbridge Rd.
+1-800-805-5223
400 Stockbridge Rd., Great Barrington, MA 01230 +1-800-805-5223 ~5.33 miles south of Stockbridge
  • Inexpensive Resort property
  • Free complimentary breakfast
From£34
Average 3.0 /5 Guest Reviews Call BookMore Details
The Dewey by The Lenox Collection in Lenox
+1-888-965-1860
7 Hubbard St., Lenox, MA 01240 +1-888-965-1860 ~5.57 miles north of Stockbridge
  • 4-star hotel
  • 12 rooms in property
From£54
Average 3.0 /5 Read Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi - Great Barrington
+1-888-788-5576
249 Stockbridge Rd., Great Barrington, MA 01230 Website +1-888-788-5576 ~5.68 miles south of Stockbridge
  • Affordable Resort property
  • 60 rooms in hotel
From£79
Very good 4.0 /5 Latest Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires - Lenox
+1-888-897-9207
203 Main St., Lenox, MA 01240 +1-888-897-9207 ~5.79 miles north of Stockbridge
  • 3-star Mountain hotel
  • 28 sleeping rooms in hotel
From£43
Very good 4.0 /5 Recent Reviews Call BookMore Details
Eastover Estate & Retreat : 430 East St.
+1-888-311-4278
430 East St., Lenox, MA 01240 +1-888-311-4278 ~6.53 miles northeast of Stockbridge
  • Four-star Mountain property
  • Check-in: 4:00PM
From£79
Average 3.5 /5 Read Reviews Call BookMore Details
Element Lenox Berkshires in Lenox
+1-888-469-4795
130 Pittsfield Rd., Lenox, MA 01240 +1-888-469-4795 ~6.91 miles north of Stockbridge
  • Three Star Mountain hotel
  • Hotel has 118 rooms
From£36
Average 3.0 /5 Reviews Call BookMore Details
Quality Inn in Great Barrington
+1-888-734-9421
372 Main St., Great Barrington, MA 01230 Website +1-888-734-9421 ~6.97 miles south of Stockbridge
  • Cheap Rural property
  • Fitness + Health Center
From£73
Very good 4.0 /5 Review Score Call BookMore Details
Life House Berkshires
+1-888-841-5292
194 Pittsfield Rd., Lenox, MA 01240 +1-888-841-5292 ~7.23 miles north of Stockbridge
  • Two star Suburban hotel
  • Check-in time: 2pm
From£35
Average 3.0 /5 Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox in Lenox
+1-888-455-5160
462 Pittsfield Rd., Lenox, MA 01240 +1-888-455-5160 ~7.42 miles north of Stockbridge
  • 2 star Resort property
  • 2 floors in property
From£47
Average 3.0 /5 Review Score Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only
+1-888-965-8297
55 Lee Rd., Lenox, MA 01240 +1-888-965-8297 ~7.99 miles north of Stockbridge
  • Expensive Resort hotel
  • 10 meeting rooms in property
From£101
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox - Lenox
+1-888-906-6358
445 Pittsfield Rd., Lenox, MA 01240 +1-888-906-6358 ~8.39 miles north of Stockbridge
  • 3 star Mountain property
  • Complimentary breakfast is offered
From£79
Average 3.0 /5 Guest Reviews Call BookMore Details
Yankee Inn : 461 Pittsfield Rd.
+1-888-749-6785
461 Pittsfield Rd., Lenox, MA 01240 +1-888-749-6785 ~8.45 miles north of Stockbridge
  • Two-star property
  • 96 rooms in property
From£106
Very good 4.0 /5 Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center
+1-888-878-9982
802 State Rd., Richmond, MA 01254 +1-888-878-9982 ~8.46 miles north of Stockbridge
  • Mid-scale Rural property
  • Free comp. breakfast
From£109
Very good 4.5 /5 Reviews Call BookMore Details
Knights Inn Lenox : 474 Pittsfield Rd.
+1-888-389-4485
474 Pittsfield Rd., Lenox, MA 01240 +1-888-389-4485 ~8.49 miles north of Stockbridge
  • 2 star Downtown hotel
  • Check-in time: 2.00 pm
Lenox Inn in Lenox
+1-888-389-4121
525 Pittsfield Rd., Lenox, MA 01240 +1-888-389-4121 ~8.72 miles north of Stockbridge
  • 2-star property
  • 18 rooms in hotel
From£43
Poor 2.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield - Pittsfield
+1-888-675-2083
1032 South St., Pittsfield, MA 01201 +1-888-675-2083 ~8.78 miles north of Stockbridge
  • 3-star Suburban property
  • 95 rooms in property
From£69
Very good 4.0 /5 Latest Reviews Call BookMore Details
Berkshire Mountain Lodge - Pittsfield
+1-800-716-8490
8 Dan Fox Dr., Pittsfield, MA 01201 +1-800-716-8490 ~9.12 miles north of Stockbridge
  • Two-star Mountain hotel
  • Gym is available on property
From£91
Very good 4.5 /5 Hotel Reviews Call BookMore Details
The Windflower Inn in Great Barrington
+1-800-805-5223
684 South Egremont Rd., Great Barrington, MA 01230 +1-800-805-5223 ~9.43 miles southwest of Stockbridge
  • 3 star Mountain hotel
  • Comp. Breakfast
From£135
Excellent 5.0 /5 Hotel Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites
+1-888-965-1860
1350 West Housatonic St., Pittsfield, MA 01201 +1-888-965-1860 ~10.13 miles north of Stockbridge
  • 3-star Rural property
  • Check-in time: 03:00
From£62
Very good 4.5 /5 Guest Reviews Call BookMore Details
Berkshire Inn in Pittsfield
+1-888-788-5576
150 West Housatonic St., Pittsfield, MA 01201 +1-888-788-5576 ~11.21 miles north of Stockbridge
  • Cheap Downtown hotel
  • 2 floors in hotel
From£65
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG
+1-888-897-9207
1 West St., Pittsfield, MA 01201 +1-888-897-9207 ~11.60 miles north of Stockbridge
  • Affordable Downtown hotel
  • Gym is available on property
From£58
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hotel on North
+1-888-311-4278
297 North St., Pittsfield, MA 01201 +1-888-311-4278 ~11.92 miles north of Stockbridge
  • 4 star Downtown property
  • Hotel has 45 rooms
From£109
Excellent 5.0 /5 Guest Reviews Call BookMore Details
Econo Lodge in Pittsfield
+1-888-469-4795
16 Cheshire Rd., Pittsfield, MA 01201 +1-888-469-4795 ~13.90 miles northeast of Stockbridge
  • Low-priced Downtown hotel
  • 58 rooms in hotel
From£35
Poor 2.0 /5 Reviews Call BookMore Details
Club Wyndham Bentley Brook
+1-888-734-9421
1 Corey Rd., Hancock, MA 01237 +1-888-734-9421 ~18.54 miles north of Stockbridge
  • Mid-scale Mountain property
  • Hotel has 152 rooms
From£65
Very good 4.0 /5 Review Score Call BookMore Details
Jiminy Peak Mountain Resort in Hancock
+1-888-841-5292
37 Corey Rd., Hancock, MA 01237 +1-888-841-5292 ~18.74 miles north of Stockbridge
  • Affordable Mountain property
  • Hotel has 7 meeting rooms
From£76
Very good 4.0 /5 Reviews Call BookMore Details
Vacation Village in The Berkshires - Lanesborough
+1-888-455-5160
276 Brodie Mtn Rd., Lanesborough, MA 01237 +1-888-455-5160 ~19.49 miles north of Stockbridge
  • 3 star Mountain hotel
  • Fitness / Gym is on-site
From£54
Very good 4.0 /5 Reviews Call BookMore Details
Blackberry River Inn
+1-888-965-8297
538 Greenwoods Rd. West, Norfolk, CT 06058 +1-888-965-8297 ~19.82 miles south of Stockbridge
  • Three Star hotel
  • Hotel has 17 rooms
From£79
Very good 4.0 /5 Recent Reviews Call BookMore Details
Manor House Inn
+1-888-906-6358
69 Maple Ave., Norfolk, CT 06058 +1-888-906-6358 ~21.30 miles south of Stockbridge
  • Mid-scale Rural hotel
  • Check in time: 3:00pm
From£175
Very good 4.0 /5 Review Score Call BookMore Details
Wake Robin Inn : 106 Sharon Rd.
+1-888-749-6785
106 Sharon Rd., Lakeville, CT 06039 +1-888-749-6785 ~23.47 miles south of Stockbridge
  • Affordable Rural property
  • 3 meeting rooms in property
From£65
Average 3.0 /5 Review Score Call BookMore Details
St. Charles Hotel : 16 Park Place
+1-888-878-9982
16 Park Place, Hudson, NY 12534 +1-888-878-9982 ~23.74 miles west of Stockbridge
  • Two star Downtown hotel
  • 6 suites in hotel
From£58
Average 3.0 /5 Recent Reviews Call BookMore Details

Next: See My Stockbridge Hotels with Pricing

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.

"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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