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 - Stockbridge
+1-888-389-4121
30 Main St., Stockbridge, MA 01262 +1-888-389-4121
  • Mid-scale Rural hotel
  • 125 sleeping rooms in hotel
From$80
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort : 190 Meadow St.
+1-888-675-2083
190 Meadow St., South Lee, MA 01260 +1-888-675-2083 ~2.56 miles east of Stockbridge
  • Affordable Mountain property
  • Has environment-friendly policy See more
From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington in Lee
+1-800-716-8490
980 Pleasant St., Lee, MA 01238 +1-800-716-8490 ~3.05 miles east of Stockbridge
  • Inexpensive hotel
  • Check in time: 11:00
From$48
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
  • Cheap hotel
  • 16 sleeping rooms in hotel
From$60
Average 3.0 /5 Recent 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 complimentary breakfast
From$160
Very Good 4.0 /5 Review Score 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
  • Low-priced property
  • Check in: 11:00
From$60
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
  • Affordable hotel
From$90
Very Good 4.5 /5 Read Reviews Call BookMore Details
33 Main : 33 Main St.
+1-888-311-4278
33 Main St., Lenox, MA 01238 +1-888-311-4278 ~3.85 miles east of Stockbridge
  • Luxurious 5-star hotel
From$200
Average 3.0 /5 Read Reviews Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel - Lee
+1-888-469-4795
435 Laurel St., Lee, MA 01238 +1-888-469-4795 ~3.90 miles northeast of Stockbridge
  • Affordable Lake hotel
  • Fitness center on property
From$60
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
  • High-end Resort property
  • Has environment-friendly policy See more
From$184
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Quality Inn
+1-888-841-5292
435 Laurel St., Lee, MA 01238 Website +1-888-841-5292 ~3.91 miles northeast of Stockbridge
  • Affordable Lake hotel
  • Free breakfast
From$65
Very Good 4.0 /5 Read Reviews Call BookMore Details
Wheatleigh - Lenox
+1-888-455-5160
Hawthorne Rd., Lenox, MA 01240 +1-888-455-5160 ~4.03 miles north of Stockbridge
  • Affordable property
  • 19 sleeping rooms in hotel
From$400
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Pilgrim Inn
+1-888-965-8297
165 Housatonic St., Lee, MA 01238 +1-888-965-8297 ~4.11 miles east of Stockbridge
  • 3 star property
  • Check-in: 3:00 PM
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Canyon Ranch Lenox - Lenox
+1-888-906-6358
165 Kemble St., Lenox, MA 01240 +1-888-906-6358 ~4.46 miles northeast of Stockbridge
  • 3 star property
  • Shuttle from airport available
From$90
Average 3.0 /5 Latest Reviews Call BookMore Details
Apple Tree Inn
+1-888-749-6785
10 Richmond Mountain Rd., Lenox, MA 01240 +1-888-749-6785 ~4.58 miles north of Stockbridge
  • High-end Mountain hotel
  • 3 floors in property
From$100
Average 3.0 /5 Reviews Call BookMore Details
Brook Farm Inn in Lenox
+1-888-878-9982
15 Hawthorne St., Lenox, MA 01240 +1-888-878-9982 ~4.78 miles north of Stockbridge
  • High-end Rural property
  • Complimentary breakfast is offered
From$120
Very Good 4.0 /5 Read Reviews Call BookMore Details
Kemble Inn : 2 Kemble St.
+1-888-389-4485
2 Kemble St., Lenox, MA 01240 +1-888-389-4485 ~5.03 miles northeast of Stockbridge
  • Midscale Mountain property
  • Hotel has an eco-friendly policy See more
From$265
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 property
  • Hotel has 3 floors
From$225
Average 3.0 /5 Recent 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
  • Mid-scale property
  • Check-in: 14:00
From$200
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Great Barrington in Great Barrington
+1-800-716-8490
415 Stockbridge Rd., Great Barrington, MA 01230 +1-800-716-8490 ~5.23 miles south of Stockbridge
  • Three Star Mountain hotel
  • 78 sleeping rooms in hotel
From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires - Great Barrington
+1-800-805-5223
400 Stockbridge Rd., Great Barrington, MA 01230 +1-800-805-5223 ~5.33 miles south of Stockbridge
  • Two-star Resort property
  • Check in: 11:00 AM
From$47
Average 3.0 /5 Read Reviews Call BookMore Details
The Dewey by The Lenox Collection : 7 Hubbard St.
+1-888-965-1860
7 Hubbard St., Lenox, MA 01240 +1-888-965-1860 ~5.57 miles north of Stockbridge
  • 4-star property
  • 2 floors in hotel
From$75
Average 3.0 /5 Recent Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi : 249 Stockbridge Rd.
+1-888-788-5576
249 Stockbridge Rd., Great Barrington, MA 01230 Website +1-888-788-5576 ~5.68 miles south of Stockbridge
  • Three Star Resort hotel
  • 60 rooms in hotel
From$109
Very Good 4.0 /5 Review Score Call BookMore Details
The Cornell Inn, Lenox & The Berkshires
+1-888-897-9207
203 Main St., Lenox, MA 01240 +1-888-897-9207 ~5.79 miles north of Stockbridge
  • Midscale Mountain hotel
  • Free complimentary breakfast
From$60
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Eastover Estate & Retreat - Lenox
+1-888-311-4278
430 East St., Lenox, MA 01240 +1-888-311-4278 ~6.53 miles northeast of Stockbridge
  • 4-star Mountain property
  • Hotel has 10 meeting rooms
From$109
Average 3.5 /5 Hotel Reviews Call BookMore Details
Element Lenox Berkshires
+1-888-469-4795
130 Pittsfield Rd., Lenox, MA 01240 +1-888-469-4795 ~6.91 miles north of Stockbridge
  • Midscale Mountain property
  • 2 floors in hotel
From$50
Average 3.0 /5 Reviews Call BookMore Details
Quality Inn
+1-888-734-9421
372 Main St., Great Barrington, MA 01230 Website +1-888-734-9421 ~6.97 miles south of Stockbridge
  • Two-star Rural hotel
  • 2 floors in hotel
From$100
Very Good 4.0 /5 Reviews Call BookMore Details
Life House Berkshires : 194 Pittsfield Rd.
+1-888-841-5292
194 Pittsfield Rd., Lenox, MA 01240 +1-888-841-5292 ~7.23 miles north of Stockbridge
  • Low-priced Suburban hotel
  • Check in time: 2pm
From$49
Average 3.0 /5 Read 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
  • Two star Resort hotel
  • 44 rooms in property
From$65
Average 3.0 /5 Hotel Reviews 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
  • High-end Resort hotel
  • Hotel has 10 meeting rooms
From$138
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox
+1-888-906-6358
445 Pittsfield Rd., Lenox, MA 01240 +1-888-906-6358 ~8.39 miles north of Stockbridge
  • Mid-scale Mountain property
  • 3 floors in hotel
From$109
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Yankee Trademark Collection by Wyndham - Lenox
+1-888-749-6785
461 Pittsfield Rd., Lenox, MA 01240 +1-888-749-6785 ~8.45 miles north of Stockbridge
  • Two-star property
  • 9 suites in hotel
From$145
Very Good 4.0 /5 Read 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 hotel
  • Hotel has 3 floors
From$150
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Knights Inn Lenox in Lenox
+1-888-389-4485
474 Pittsfield Rd., Lenox, MA 01240 +1-888-389-4485 ~8.49 miles north of Stockbridge
  • Low priced Downtown property
  • Check in: 2.00 pm
Lenox Inn
+1-888-389-4121
525 Pittsfield Rd., Lenox, MA 01240 +1-888-389-4121 ~8.72 miles north of Stockbridge
  • Cheap property
  • 18 sleeping rooms in hotel
Hilton Garden Inn Lenox Pittsfield in Pittsfield
+1-888-675-2083
1032 South St., Pittsfield, MA 01201 +1-888-675-2083 ~8.78 miles north of Stockbridge
  • 3 star Suburban hotel
  • 4 floors in hotel
From$95
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Berkshire Mountain Lodge
+1-800-716-8490
8 Dan Fox Dr., Pittsfield, MA 01201 +1-800-716-8490 ~9.12 miles north of Stockbridge
  • Low priced Mountain hotel
  • Hotel has 146 rooms
From$125
Very Good 4.5 /5 Latest Reviews Call BookMore Details
The Windflower Inn : 684 South Egremont Rd.
+1-800-805-5223
684 South Egremont Rd., Great Barrington, MA 01230 +1-800-805-5223 ~9.43 miles southwest of Stockbridge
  • Midscale Mountain hotel
  • Free breakfast
From$185
Excellent 5.0 /5 Guest Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites - Pittsfield
+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: 03:00
From$85
Very Good 4.5 /5 Reviews Call BookMore Details
Berkshire Inn
+1-888-788-5576
150 West Housatonic St., Pittsfield, MA 01201 +1-888-788-5576 ~11.21 miles north of Stockbridge
  • Inexpensive Downtown property
  • Fitness + Health Center
From$90
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG : 1 West St.
+1-888-897-9207
1 West St., Pittsfield, MA 01201 +1-888-897-9207 ~11.60 miles north of Stockbridge
  • 3 star Downtown property
  • Access to gym on-site
From$80
Average 3.0 /5 Read 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
  • High-end Downtown hotel
  • 6 suites in hotel
From$150
Excellent 5.0 /5 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
  • Hotel has 58 rooms
From$48
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
  • 3 star Mountain property
  • 152 sleeping rooms in hotel
From$90
Very Good 4.0 /5 Read Reviews 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
  • 102 suites in property
From$105
Very Good 4.0 /5 Review Score Call BookMore Details
Vacation Village in The Berkshires in 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
  • 5 floors in hotel
From$75
Very Good 4.0 /5 Reviews Call BookMore Details
Blackberry River Inn in Norfolk
+1-888-965-8297
538 Greenwoods Rd. West, Norfolk, CT 06058 +1-888-965-8297 ~19.82 miles south of Stockbridge
  • Affordable hotel
  • Hotel has 17 rooms
From$109
Very Good 4.0 /5 Read Reviews Call BookMore Details
Manor House Inn in Norfolk
+1-888-906-6358
69 Maple Ave., Norfolk, CT 06058 +1-888-906-6358 ~21.30 miles south of Stockbridge
  • 3-star Rural hotel
  • Complimentary breakfast is offered
From$240
Very Good 4.0 /5 Recent Reviews 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
  • Mid-scale Rural property
  • 38 sleeping rooms in hotel
From$89
Average 3.0 /5 Review Score Call BookMore Details
St. Charles Hotel
+1-888-878-9982
16 Park Place, Hudson, NY 12534 +1-888-878-9982 ~23.74 miles west of Stockbridge
  • Cheap Downtown property
  • Check in time: 4:00 PM
From$80
Average 3.0 /5 Hotel 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.

"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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