Lodging 2017-07-10T14:45:45+00:00


When Norman Rockwell described Stockbridge as “the Best of America, the Best of New England,” he may have been influenced by the town’s architectural landscape, as well as its tradition of extending hospitality to visitors.

Today the town’s innkeepers help preserve the areas historic character and maintain its heritage of welcoming guests, while providing the modern amenities travelers have come to expect.

Whether you prefer an historic inn, charming B&B or a newer property, be sure to make your reservations well in advance if you’re planning to visit the Berkshires during the popular summer or fall foliage seasons.

1862 Seasons on Main

Elegant, Restored, Romantic, Victorian 150 year old Boutique Inn, listed on the National Register of Historic Places and located on Main Street, walking distance to shops, restaurants and galleries.

47 Main Street
Stockbridge, MA 01262

(413) 298-5419





31 Stockbridge Road

Rent a comfortable historic 1840’s farmhouse that sits on 26 acres. Centrally located. Walk to town & swimming.  5 bedrooms, 3 1/2 baths. Sleeps 12. Eat-in-kitchen. Dining Room seats 12.  Fully equipped.  W/D,Cable/SAT/DVD/CD/WiFi

31 Stockbridge Road
West Stockbridge, MA 01266






An English Hideaway B&B

A quaint 1780’s cottage in the heart of the Berkshires. Warmth, Hospitality, Great food awaits you! Call for our specials!

325 North Plain Road
Housatonic, MA 01236

(413) 274-6149





Applegate Inn

Savor the tranquility at Applegate Inn an elegant six-acre estate. Relax & enjoy candlelit gourmet breakfasts. Rooms with private bath, whirlpool tubs, fireplaces, AC, wifi, heated pool. Golf/tennis across the road. In-between Jacob’s Pillow and Tanglewood.

279 West Park Street
Lee, MA 01238

(413) 243-4451





Berkshire Days Inn

New pillow top mattresses and bedding, new carpet. Free Sunshine Breakfast. Walk to historic downtown with restaurants, shops, theatre.

372 Main Street
Great Barrington, MA 01230






Chambery Inn

With French-inspired design and nine exceptional rooms, this nineteenth-century parochial school turned country inn possesses a unique character that celebrates it as a truly distinctive landmark in the beautiful Berkshire Hills. Located in the heart of Lee, Massachusetts, this unique historic hostelry has delighted guests since its opening in 1990.

199 Main Street
Lee, MA 01238

(800) 537-4321
(413) 243-2221





Chesapeake Inn of Lenox

Best of Citysearch – 1/4 mile to Tanglewood “Whatever & Whenever” full breakfast, Sat BBQ, A/C, 75ft heated lap pool, Wi-Fi, Public rooms, outdoor sitting areas, parking. Total service caters to needs, wants, desires

210 West Street
Lenox, MA 01240

(800) 966-3429
(413) 637-3429
(717) 326-5134





Conroy’s B&B

History, Culture, Nature, Stockbridge has it all, and our classic 1828 farmhouse and detached summer apt. and pool stand in its midst. For 25 years, we have welcomed strangers who leave as friends. Healthy breakfasts, comfortable rooms, helpful staff & convenient location bring folks back yearly. Minutes to Tanglewood, Rockwell Museum, theatre!

P.O. Box 191
11 East Street, Rte 7N
Stockbridge, MA 01262

(888) 298-4990
(413) 298-4990





Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott is located minutes from downtown Lenox and Stockcbridge, in the heart of beautiful Berkshire County. Close to Tanglewood, Jacobs Pillow, Norman Rockwell Museum and plenty of outdoor activities. We offer stylish rooms, The Bisto(Breakfast, Beverages, Dinner), free WiFi, fitness center, indoor pool.

PO Box 829
70 Pittsfield Road
Lenox, MA 01240

(413) 551-7700 (888) 236-2427



Cranwell Spa and Golf Resort


Historic 105-room resort with Gilded-Age Mansion, spa, in/outdoor pool, 18-hole golf course, tennis, x-c skiing, & 3 restaurants. Open to public year-round.
Musical Satire group, Capitol Steps, performs June 30 – September 1, 2017. Shows nightly at 8:00pm (excl. Tues), pre-dinner offered.

55 Lee Road
Lenox, 01240

(413) 637-1364
(800) 272-6935





Devonfield Country Inn B&B

29 acres shaded by birch trees with rolling tapestry of Berkshire Hills beyond. Private baths, fireplaces, Jucuzzis, full breakfast, exercise room, tennis ct, heated pool & Greenock Golf Club is 6 iron shot away.

85 Stockbridge Road
Lee, MA 01238

(800) 664-0880
(413) 243-3298





Fairfield Inn & Suites Lenox/Great Barrington

Award winning Marriott conveniently located to everything in Historic Great Barrington. Helpful & friendly staff. 93 spacious rooms and suites. FREE Wi-Fi.
Free hot, breakfast buffet. 24 hour exercise room. Indoor heated pool and spa.1200 square feet of state-of-the art meeting space. Groups welcome

249 Stockbridge Road (Rte 7)
Gt. Barrington, MA 01230

(413) 644-3200






Federal House Inn

In this beautifully restored federal style 1824 inn, you will enjoy a warm and welcoming atmosphere along with bright sunny rooms, gourmet candlelight breakfast, complimentary wine and hors d’oeuvres all within minutes to Tanglewood and other area attractions.

1560 Pleasant Street
Lee, MA 01238

Mailing: P.O. Box 243
South Lee, MA 01260

(800) 243-1824
(413) 243-1824





Hampton Inn & Suites

The award-winning Hampton Inn & Suites is located in the heart of the Berkshires, nestled on 111 acres of a wildlife preserve offering many nature trails to explore. With free hot breakfast, WI-FI, and an indoor heated pool we are the perfect place to stay in the Berkshires. Smiles, cookies and free hot beverages are waiting to welcome you.

PO Box 1795
445 Pittsfield Road
Lenox, MA 01240

(413) 499-1111





Hilton Garden Inn Lenox/Pittsfield

Award-winning! Top 2% of ALL HGI’s! Conveniently located on Rte 7 & 20 near many attractions and businesses. 95 guest rooms with microwave/refrigerator. Free wifi. Indoor heated pool/hot tub, 24-hour fitness room. On-site Garden Grille & Bar Restaurant serving breakfast, dinner & room service or enjoy your favorite cocktail on our outdoor patio!

1032 South Street, Route 7
Pittsfield, MA 01201

(413) 448-2222




Kripalu Center for Yoga & Health

The premiere destination for individuals and organizations seeking a joyful, inclusive, and compassionate environment for wellness, learning, and retreat. Home to the Kripalu Schools, offering certification programs to yoga teaching and Ayurvedic practitioners, we are a tax-exempt 501(c)(3) nonprofit organization.

57 Interlaken Road
PO Box 309
Stockbridge, MA 01262

(800) 741-7353





Lantern House Motel

2 Diamond AAA. 14 rms/pillow top mattress/AC/TV/pool/refrig. Min to Simon’s Rock/Rockwell/Tanglewood/Butternut/Catamount/Stockbridge. Renovated.

256 Stockbridge Road
Great Barrington, MA 01230

(413) 528-2350





Monument Mountain Motel

AAA Approval, All rooms have new Bathrooms, new Bedding, Wireless internet, Microwave & Refrigerator. Some rooms pet friendly. Walking distance to many restaurants. Outdoor pool.

247 Stockbridge Road
Great Barrington, MA 01230

(413) 528-3272





Shaker Mill Inn

We offer spacious rooms with private entry, private baths, great in-room breakfast and unmatched hospitality. Children, Pet and TAG friendly.

Box 191
7 Albany Road
West Stockbridge, MA 01266

(877) 385-2484
(413) 232-4600





Stockbridge Country Inn

An Historic Stockbridge Inn welcoming guests for more than 25 years – the inn features antique filled rooms which are comfy and en-suite baths with full amenities plus free wifi and summer pool – surrounded by lovely grounds. Complementary served breakfast daily – located between Norman Rockwell and Chesterwood Museums.


26 Glendale Road
Rte. 183, PO Box 525
Stockbridge, MA 01262

(413) 298-4015



The Cottage

Located on 2 acres with beautiful mountain views, The Cottage is a quiet home away from home. The Cottage is perfectly located close to Tanglewood, the Norman Rockwell Museum, The Marian Fathers, theaters and museums. The suites are spacious and well appointed, perfect for short or long stays. Come to The Berkshires and be our guest

PO Box 1207
Stockbridge, MA 01262






The Inn at Stockbridge

Our historic Berkshire inn, built in 1906 and situated on 12 acres, features 8 luxury suites in our renovated barn and cottage house and 7 traditional rooms in the main house. We offer five-star, home-cooked breakfasts every day and a complemintery wine and cheese reception each evening.

30 East Street
PO Box 618
Stockbridge, MA 01262

(888) 819-2373
(413) 298-3337





The Red Lion Inn

A charter member of Historic Hotels of America, The Red Lion Inn (c. 1773) has been providing food and lodging to guests for more than two centuries. With the addition of its ninth Village Guest House Maple Glen, the Inn offers 125 antique-filled rooms and suites, a gift shop featuring locally made items and a full range of amenities including free WiFi, and a year-round heated outdoor pool.The Inn is recommended by National Geographic Traveler, The New York Times and The Boston Globe.

P.O. Box 954
30 Main Street
Stockbridge, MA 01262

(413) 298-5545





The Redway House

Disappear from it all and be close to everything. Stay at The Redway House (Circa 1757), a quiet 3-bedroom, vacation rental house, nestled within 114 acres of forestland in Stockbridge. For information, rates and online reservations visit us on the web at www.redwayhouse.com.


5 West Dale Road
Stockbridge, MA 01262

(877) 818-1013




Leading Hotels of the World.  From the original bedrooms of the Count and Countess to the aviary converted into a two story suite and made famous by Leonard Bernstein, each of the nineteen guest rooms is unique and individually decorated. The sensibility of contemporary design is combined with well chosen English and French antiques to enhance Wheatleigh’s classical Renaissance architecture.

P.O. Box 824
Hawthorne Road
Lenox, MA 01240

(413) 637 0610