A picture-perfect New England spot, Stockbridge evokes tranquil scenes of streets lined with clapboard houses, where rocking chairs creak on big verandas and heritage shopfronts are tucked behind leafy trees. Made famous by resident artist Norman Rockwell, the community is immensely popular with travellers looking to soak up the striking scenery and intriguing artsy history of the Berkshires. Quaint and pretty, the town offers some great accommodation options, including self-catering cottages and charming heritage inns fit for a range of budgets. The best places to stay in Stockbridge are laid-back and historic, perfectly in tune with the town’s vibe.

Head to the Norman Rockwell Museum to admire the largest collection of the artist’s work — including books, posters and magazines — as well as his studio. Other heritage sites of interest include Mission House, the Gilded Age Naumkeag Estate, and Chesterwood Estate, once the home and studio of Victorian sculptor Daniel Chester French. Step back in time at the Hancock Shaker Village Museum, not far from Stockbridge, or visit the museums of lovely Lenox.

Outdoorsy holidaymakers can hire bikes to cycle around the Berkshire Hills, go hiking in the 1300-acre Pleasant Valley Wilderness Sanctuary, or explore October Mountain State Forest. Follow a stretch of the Appalachian Trail through copses of hemlocks, spruces, birches and oaks, or enjoy canoeing, horse riding and wildlife-spotting. Stockbridge Golf Club is also a beautiful place for a round of golf.

Back in town, you’ll find shops and eateries aplenty. Don’t miss grabbing a drink at The Red Lion Inn — also one of the best places to stay in Stockbridge!

The Best Places to Stay in Stockbridge

For Families or Groups

• The Red Lion Inn dates back to 1773, and is a wonderful choice for families or groups keen to stay in central Stockbridge and soak up its old-school charm. Highlights include an outdoor pool, onsite yoga and fitness centre, pet-friendly accommodation and multiple dining options — including a pub and tavern. Book a room in the main house, or stay in one of the generously-proportioned village residences, where there's space for the whole family!

For an intimate hideaway

• The Inn at Stockbridge is a gorgeous B&B in a Georgian-style mansion. Many of the 16 romantic rooms and suites come with fireplaces and big whirlpool tubs. Unwind in six acres of gardens, take a dip in the pool and feast on gourmet, garden-grown breakfasts before heading out to explore. A tranquil couples' choice, complete with wine & cheese evenings.
• The Stockbridge Country Inn offers eight charming suites with antique furnishings, chintz and pretty wallpapers. Within walking distance of the Norman Rockwell Museum and Chesterwood Estate, this is a great pick for history buffs looking to experience traditional Stockbridge. Expect 4 acres of verdant grounds and a swimming pool. Intimate and laid-back.

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!

STILL NOT SURE?

• Browse our list of the best places to stay in Lenox.
• Expand your search to include all the best places to stay in Massachusetts.
• Or contact one of our friendly Gurus for advice.