Stockbridge

Culture4.8/5

Norman Rockwell Museum

Nestled in the charming town of Stockbridge, MA, the Norman Rockwell Museum is a delightful treasure trove of Americana! Dance through the enchanting galleries filled with Rockwell’s iconic illustrations that capture the heart of everyday life. Don’t miss the stunning outdoor sculptures and beautiful grounds—perfect for a picnic! A must-visit for art lovers and nostalgia seekers alike!

Culture4.7/5

Chesterwood

Chesterwood, the summer home of sculptor Daniel Chester French, captivates visitors with its stunning landscapes and rich artistic history, showcasing iconic works like the Lincoln statue while providing a serene retreat in the Berkshires.

Culture4.7/5

Naumkeag

Naumkeag is a whimsical Gilded Age mansion surrounded by stunning gardens in Stockbridge, MA. Step back in time as you wander through the historic rooms filled with unique decor and intricate details. Don't miss the famous Blue Steps which lead down to colorful terraces and breathtaking views. A must-see for any history buff or garden enthusiast!

Culture4.8/5

Bidwell House Museum

Nestled in the Berkshires, Bidwell House Museum offers a glimpse into 18th-century life with its meticulously preserved historic home and stunning landscapes, making it a captivating destination for history enthusiasts and nature lovers alike.

Landmark4.8/5

Tanglewood

Lenox's concert venue is the Boston Symphony Orchestra's summer home, with performances in a pavilion and on a broad lawn. People spread picnics on the grass and listen beneath the Berkshire trees.

Eat$$$4.6/5

Once Upon a Table

Cafe$$4.5/5

Tiffany's Cafe & Market

This Stockbridge cafe and market serves breakfast and lunch, including a steakhouse bagel. You order at the counter rather than from a server.

Eat$$$4/5

Michaels Restaurant

Located in the quaint town of Stockbridge, Michaels is a must-stop shop for those looking for unique gifts and artisanal goods. With a cozy atmosphere and friendly staff, this charming store on Elm St offers a delightful selection of handmade crafts, local artwork, and specialty items. Don't miss out on this hidden gem!

Cafe$$4.7/5

Stockbridge Coffee & Tea

Stay$$$$4.3/5

The Cornell Inn, Lenox & The Berkshires

Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped with cable TV, high-speed internet, and coffee machines. Many rooms feature fireplaces and private balconies. The Boston Symphony Orchestra's Tangle wood Institute is five minutes away, and the restaurants of Lenox are 1 minute away. A table-served gourmet breakfast (not a buffet) is included with your room, and it includes your choice of espressos, cappuccinos, lattes, Americano, regular coffee, or imported chocolate hot chocolate. Guests can relax on our private deck next to a koi pond and waterfall, or enjoy the gardens that connect directly to the beautiful Kennedy Park. The Cornell is within 1 mile of shopping and dining. Bouquet Ski Area and Berkshire Scenic Railway Museum are 10 minutes’ drive.

Stay4.05/5

The Red Lion Inn

Nestled in the heart of central Stockbridge, Massachusetts, this historic hotel offers luxurious accommodations, friendly service and gourmet on-site dining options. We are only a short distance from area points of interest. The Red Lion Inn elegantly combines old-world charm including antiques, tea pots and a birdcage lift with many modern amenities, including free Wi-Fi. Guests at the hotel can also enjoy the year-round outdoor pool and hot tub and an on-site gift shop. While staying at the Red Lion, guests can enjoy delicious on-site dining options at the hotel's restaurants, The Main Dining Room & Widow Bingham's Tavern both serving classic American cuisine. The Red Lion Inn offers convenient access to a number of area attractions, including the Norman Rockwell Museum. Historic homes, antique shops, boutiques and beautiful gardens are also nearby.

Stay$$$$4.25/5

Hampton Terrace Inn

Hampton Terrace Inn in Lenox is housed in a historic building, offering a unique and charming atmosphere. Guests enjoy a sun terrace, garden, restaurant, bar, tennis court, seasonal outdoor swimming pool, and free WiFi. Rooms feature air-conditioning, private bathrooms, and amenities such as a hot tub, pool with a view, and garden views. The traditional, romantic restaurant serves American cuisine with vegetarian, vegan, gluten-free, and dairy-free options. Located 78 km from Albany International Airport, nearby attractions include Devries Fine Art (8-minute walk) and Tanglewood (2.6 km).

Stay4.9/5

The Inn at Stockbridge

Get ready for a wicked awesome stay at The Inn at Stockbridge! Located in the heart of Stockbridge, MA, this charming inn is perfect for exploring the scenic Berkshires. Cozy rooms, scrumptious breakfast, and friendly staff - it's like staying with your quirkiest Aunt Mabel. Plus, nearby attractions like Tanglewood and Norman Rockwell Museum will have you saying "Wowza!" Book your stay now!