Photo of Stockbridge

About Stockbridge

Stockbridge is picture-perfect, New England quaintness; no neon signs, no modern high-rise. Instead, pretty clap-board houses, long verandas, rocking-chairs on porches. If it sounds familiar, that’s because it was captured hundreds of times by the artist Norman Rockwell, a Stockbridge resident and illustrator for the Saturday Evening Post. Choose one of the best places to stay in Stockbridge and you’ll almost feel you’re in a Norman Rockwell painting.

The town’s museum, named after Rockwell, has the largest collection of his works - he illustrated books and posters as well as magazines - as well as his studio, which was moved here from his Stockbridge home. Considered one of the country’s most popular illustrators, he moved to the town from his native New York in the 1950s, and remained for the rest of his life. His work shows that the town has changed little since those years.

And this is the town’s great charm, along with some lovely architecture. Chesterwood estate was the summer home of the Victorian sculptor Daniel Chester French, best known for his monumental statue of Abraham Lincoln in Washington, DC. His house and studio are little changed from when he lived and worked here, with nearly 500 pieces of sculpture, finished and unfinished, in his studio.

Another attractive house is Naumkeag, a late-Victorian, eclectically furnished, Gilded Age 'cottage', the summer retreat of Joseph Hodges Choate, a former US ambassador to England. The formal gardens with their fountains, sculpture and themed plantings are a delight to wander.

Stockbridge is not a huge town to explore. After you’ve strolled the streets, admired the architecture, browsed the shops and restaurants and the famous Red Lion Inn on Main Street, hire a bike and explore the surrounding countryside. Or drive a few miles out of town to October Mountain State Forest. Here you can go canoeing or hike a stretch of the Appalachian Trail through lovely copses of hemlocks, spruces, birches and oaks.

The town is particularly popular in summer and autumn when the best places to stay in Stockbridge get booked well in advance.

The Best Places to Stay in Stockbridge

The Best Places to Stay in Stockbridge For New England Charm

  • The historic Red Lion Inn encapsulates New England loveliness with its long veranda, glowing-white facades and grand piano in the hall. Bedrooms are full of chintz and charm; there is a choice of eating options as well as an outdoor pool.

The Best Places to Stay in Stockbridge for colonial style

  • A classic colonial-style house - grand portico, wooden shutters - The Inn at Stockbridge doesn’t disappoint inside. Rooms are large and furnished in country-house style, many with private terraces. Beautiful gardens surround the house including a kitchen garden from which the restaurant benefits.

For more choices, browse our list of the best places to stay in Stockbridge. Or you can expand your search to include all our Massachusetts recommendations or contact one of our gurus for advice.

Best Hotels in Stockbridge

  • The Red Lion Inn Stockbridge (Massachusetts) 108 rooms from £117

    Towelling robes
    Romantic  -  Good for couples.
    Views  -  Great views from hotel
    Full of character

    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. See More

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  • The Inn at Stockbridge Stockbridge 15 rooms from £200

    Great walks  -  Beautiful walks in the neary Berkshire Botanical Gardens.
    Sights nearby  -  Norman Rockwell Museum .
    Swimming Pool  -  Outdoor seasonal pool.
    Full of character

    A classic, Georgian-style House, set on 12 acres of beautiful gardens. Antique furnishing, elegant drapes and warm colours lend a romantic air to the suites. On-site restaurant uses produce fresh from the kitchen garden. Unwind in style. See More

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