The best hotels in Stockbridge

Photo of Stockbridge
Credit: Flickr user Herry Lawford
Photo of Stockbridge
Credit: Flickr user Jerry and Pat Dona
Photo of Stockbridge
Credit: Flickr user Herry Lawford
All hotels in Stockbridge Apartments & villas in Stockbridge Find more hotels in Stockbridge

About Stockbridge

Tucked in the Berkshires, Stockbridge is a postcard-perfect New England town with leafy streets, historic clapboard houses, and a strong artsy spirit thanks to Norman Rockwell’s legacy. Staying here feels like stepping into a painting, and the hotels fit right in. You’ll find charming heritage inns that echo the town’s history, boutique stays with a modern twist, and family-friendly cottages close to Main Street. Wherever you check in, Stockbridge hotels capture that laid-back, quintessentially New England vibe.

Wander through the Norman Rockwell Museum, home to the largest collection of the artist’s work, or dive into history at sites like the Naumkeag Estate, the Mission House, and Chesterwood, once the studio of sculptor Daniel Chester French. A short trip takes you to Hancock Shaker Village, where life from another era comes alive, or to the elegant museums of neighbouring Lenox. If you prefer the outdoors, the rolling Berkshire Hills are perfect for biking, hiking, or even following a stretch of the Appalachian Trail beneath shady hemlocks and birches. Pleasant Valley Sanctuary and October Mountain State Forest offer wide-open spaces for wildlife spotting, canoeing, and horseback riding, while the Stockbridge Golf Club is a scenic place to tee off. Afterwards, the town’s cosy shops and restaurants beckon — and no visit is complete without a stop at The Red Lion Inn, a local institution for both a drink and a memorable stay.

The Best Places to Stay in Stockbridge

For Families or Groups

  • Since 1773, The Red Lion Inn has welcomed travellers to central Stockbridge with historic charm, family-sized residences, pet-friendly stays, and multiple dining spots. Guests enjoy an outdoor pool, yoga and fitness centre, plus classic tavern hospitality—all in one timeless New England retreat.

For an intimate hideaway

  • The Inn at Stockbridge- This Georgian-style B&B pairs romance with relaxation. Sixteen suites feature fireplaces and whirlpool tubs, while six acres of gardens, a pool, and gourmet garden-to-table breakfasts set the scene. Couples love the tranquil vibe—topped with nightly wine and cheese gatherings.
  • A cosy retreat with eight antique-filled suites, The Stockbridge Country Inn charms with chintz, wallpaper, and vintage elegance. Just steps from the Norman Rockwell Museum and Chesterwood Estate, it offers four leafy acres, a pool, and a serene, history-rich setting.

For an apartment or holiday cottage

  • If you'd prefer a self-catering option, we suggest that you visit our online partner Booking.com.

Travel information

  • Fly to Albany International Airport, an hour's drive away, or to Boston's Logan International Airport, which is just over two hours from Stockbridge. There are regular buses from both airports, but journeys can be slow.
  • The Berkshires are great for a road trip! Contact our online partner Rentalcars if you would like to hire a car.
  • Travel during the summer months (June to August) for the warmest weather, but do be aware that this is peak season. Come in the spring (April - May) or autumn (September - October) for fewer crowds and great hotel deals. Expect bitterly cold winters!

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The best hotels in Stockbridge

The Red Lion Inn, Stockbridge

The Red Lion Inn, Stockbridge

Stockbridge (Massachusetts)

1773 boutique welcomes guests with fireplace, grand piano and New England hospitality. Hop in the birdcage lift and enter old-world charm rooms with antique furnishings, large beds and modern bathrooms. Widow Bingham's Tavern and Lion's Den Pub both serve American dishes. A great countryside break.

  • Bath robes
  • Tennis Court - Four courts on site for all to use.
  • Spa
  • Restaurant
from $150 for 1 room, 1 night including taxes & fees
Check availability on Expedia
The Inn at Stockbridge

The Inn at Stockbridge

Stockbridge (Massachusetts)

A classic, Georgian-style House, set on six acres of beautiful gardens. Three unique lodgings offer fourteen spacious individually designed suites, all with high-end linens and many with fireplace too. Gourmet breakfasts feature produce fresh from the kitchen garden. Unwind in style.

  • Great walks - Beautiful walks in the neary Berkshire Botanical Gardens.
  • Sights nearby - Norman Rockwell Museum .
  • Swimming Pool - Outdoor seasonal pool.
  • Restaurant
from $256 for 1 room, 1 night including taxes & fees
The Stockbridge Country Inn

The Stockbridge Country Inn

Stockbridge (Massachusetts)

Idyllic 19th-century country house with sumptuous suites and outdoor pool. Quaint suites have been decorated to period perfection; think canopy beds, love seats, floral wallpapers and chintz draperies. Four acres of grounds ensure serene peace and quiet. Dream romantic country weekend material.

  • Romantic Break - With indulgent beds, private fireplaces and spoiling breakfasts in the sun, an ideal spot for those after grown-up romance
  • Country Escape - Spend mornings exploring the beauty of the Berkshires countryside before lazy afternoons enjoying the pool and grounds
  • Museums - For art lovers; the inn is the closest property to Norman Rockwell and Chesterwood Museums
  • Sights nearby - In the area visit Naumkeag historic estate, Berkshire Botanical Garden, Mission House and The Mount - Edith Wharton's home
from $299 for 1 room, 1 night including taxes & fees
Check availability on Expedia