[2023 PICKS] The Best Boutique Hotels in Stockbridge, Massachusetts

The best boutique hotels in Stockbridge place you in some of the most idyllic locations in Massachusetts.

Stockbridge is a charming town in the Berkshire Mountains of Western Massachusetts, USA. This picturesque New England village is a popular travel destination for those seeking a peaceful escape from the hustle and bustle of city life. The town is renowned for its historic homes, stunning landscapes, and cultural attractions, making it a favorite destination among art enthusiasts and nature lovers.

Stockbridge is also known as the birthplace of Norman Rockwell, the famous American painter and illustrator, and visitors can explore his legacy at the Norman Rockwell Museum. With its quaint Main Street, vibrant art scene, and proximity to the beautiful Berkshires, Stockbridge is a must-visit destination for anyone looking to unwind in a tranquil setting.

We hand-picked top-rated boutique hotels in Stockbridge to consider for your next getaway!

The 10 Stockbridge Boutique Hotels – Best Places to Stay

1. Wheatleigh

9.8 Average Rating
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Located in Lenox, Massachusetts, The Wheatleigh is a luxurious chateau surrounded by 22 acres of the Berkshire Mountains. It offers a variety of amenities, including free Wi-Fi, wine tastings, a seasonal outdoor pool, a tennis court, a massage room, and a fitness center. The Berkshire Botanical Gardens are only 10 minutes away by car.

The guest rooms at The Wheatleigh are equipped with plush bedding, a flat-screen TV, a fireplace, courtyard views, or a seating area. They also feature an en suite bathroom with an antique soaking tub and a large shower.

For those looking for a luxurious getaway, The Wheatleigh is the ideal destination. Hotels in Stockbridge, Massachusetts, are only a short drive away, making it the perfect option for a relaxing vacation.

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2. Life House, Berkshires

8.0 Average Rating
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Looking for the best hotels in Stockbridge, MA? Consider Life House, Berkshires, a 4-star hotel located 5.4 km from Tanglewood. The hotel offers a range of amenities, including a shared lounge, free private parking, a restaurant, and a bar. Free WiFi is also available.

The hotel’s non-smoking rooms are well-equipped with a desk, a flat-screen TV, a private bathroom, bed linen, and towels. A continental breakfast is served each morning. The reception is open 24/7, with staff speaking English, Spanish, and French.

Life House, Berkshires, is conveniently located near a number of attractions, including Tanglewood Musical Center (5.8 km), Cranwell Spa & Golf Club (5.7 km), and Norman Rockwell Museum (14 km). Albany International Airport is 76 km away.

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3. The Inn at Stockbridge

9.5 Average Rating
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The Inn at Stockbridge is one of the best hotels in Stockbridge, MA. It is located less than 3.2 km from the Berkshire Theatre Festival on 12 acres. Each room is individually styled and features an en suite bathroom, flat-screen LCD TV, and a bottle of sherry. Some rooms even have a seating area with a gas fireplace.

The hotel offers a variety of complimentary amenities for guests. These include a full breakfast each morning, free wine and cheese in the common living room during the evenings, and free coffee, tea, hot chocolate, and snacks available throughout the day. Additionally, guests can access a fitness room, a game room with a public computer, and an outdoor seasonal pool.

The Inn at Stockbridge is conveniently situated off Interstate 90. It is only a 10-minute drive from Tanglewood and Norman Rockwell Museum, while Stockbridge Golf Course is 4 km away.

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4. The Red Lion Inn

8.0 Average Rating
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If you’re looking for places to stay in Stockbridge, MA, the Red Lion Inn is an excellent choice. This historic boutique hotel offers luxurious accommodations, friendly service, and a variety of on-site dining options. Guests can use modern amenities like free Wi-Fi and an outdoor pool and hot tub. The hotel’s two restaurants, The Main Dining Room and Widow Bingham’s Tavern, serve classic American cuisine.

The Red Lion Inn is conveniently located near many attractions, including the Norman Rockwell Museum, historic homes, antique shops, boutiques, and beautiful gardens. With so many activities to enjoy in the area, the Red Lion Inn is the perfect place to stay for your visit to Stockbridge, MA.

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5. The Cottage

7.1 Average Rating
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The Cottage Bed & Breakfast is located in Stockbridge, Massachusetts, just 2 km from the Stockbridge town center. This delightful accommodation sits on two acres of hills and forest, offering stunning views of the Berkshire mountains. Guests will enjoy a private entrance to their suite, as well as an outdoor patio with a dining area, an on-site terrace and garden, and complimentary toiletries. Each suite also features a cable TV, a seating area with a sofa, a small refrigerator, a microwave, and a coffee maker.

This Stockbridge Hotel is conveniently located near several attractions, including the Norman Rockwell Museum, Stockbridge Golf Club, and the Tanglewood Music Festival, all of which are within 3 km. Butternut Ski Resort and Bousquet Ski Area are less than 16 km away, and Jiminy Peak Mountain Resort is 38.3 km away. The majestic Mount Greylock is 45 km from The Cottage.

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6. Stockbridge Country Inn

9.3 Average Rating
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Hotels in Stockbridge, Massachusetts offer a variety of amenities for guests to enjoy. The Stockbridge Country Inn is located 1.5 km from the Norman Rockwell Museum, 1 km from the Chesterwood Museum, 8.9 km from the Tanglewood Music Center, and 14.7 km from Ski Butternut. The inn is situated on four private acres of Berkshire landscape, and the Stockbridge Golf Course is 2.2 km away.

Each guestroom is appointed with a private en suite bath with full bath amenities, including cotton robes, and free WiFi access is available. Guests can enjoy a gourmet country-style breakfast daily, featuring omelets, smoked bacon, and fresh fruit, served in the dining room or enclosed terrace overlooking the lush gardens.

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7. Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel

8.3 Average Rating
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The Holiday Inn Club Vacations – Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires, an IHG Hotel, offers comfortable rooms with amenities to make your stay enjoyable. All rooms feature a flat-screen TV with satellite channels and a private bathroom. Additionally, each room includes a seating area and kitchen. Free WiFi is also available.

It’s one of the best hotels in Stockbridge, MA, which provides a range of facilities to make your stay more enjoyable, including a children’s playground. For any advice on the local area, the friendly reception team will gladly provide information.

The hotel is 41 km from Adams and 61 km from Bradley International Airport.

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8. The Black Swan Lee – Lenox, Ascend Hotel Collection

8.3 Average Rating
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For travelers looking for places to stay in Stockbridge MA, the Black Swan Lee – Lenox Ascend Hotel Collection is an ideal choice. Located in the foothills of the Berkshire Mountains, this hotel is close to several attractions and local points of interest, like the Tanglewood Music Festival, the Norman Rockwell Museum, Jacob’s Pillow, and many outdoor recreational opportunities. Guests can enjoy the sparkling Laurel Lake in the hotel’s backyard, where they can go swimming, fishing, or boating.

There are golf courses, ski slopes, and parks nearby, as well as Ski Butternut, which is a short distance away. The Lee Premium Outlets are also close by for a day of shopping. The Bombay Bar & Grill, located on the premises, offers guests a delicious meal or cocktail, and the perfect way to end the day is to watch the sunset over the lake.

The Black Swan Lee – Lenox Ascend Hotel Collection offers a variety of amenities, including free wireless high-speed Internet access, local calls, and non-smoking guest rooms that are equipped with refrigerators, Keurig coffee makers, hair dryers, irons, ironing boards, desks, and cable TV. Some rooms even feature balconies and whirlpool bathtubs. For those looking for places to stay in Stockbridge MA, the Black Swan Lee – Lenox Ascend Hotel Collection is the perfect choice.

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9. The Whitlock

8.2 Average Rating
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The Whitlock is a 3-star hotel situated in Lenox, Massachusetts. It is located within 2.1 km of Tanglewood and 2.4 km of Tanglewood Musical Center. This boutique hotel in Stockbridge offers a bar and free private parking for driving guests.

Each of the air-conditioned rooms in the property comes with free WiFi and a private bathroom. The units are also equipped with a flat-screen TV with satellite channels, and bed linen and towels are provided.

The hotel has a garden and a sun terrace. Guests can enjoy activities in and around Lenox, such as skiing and cycling. Norman Rockwell Museum is 11 km away, while Great Falls is 41 km away. The nearest airport is Albany International Airport, 78 km from The Whitlock.

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10. Hampton Terrace Inn

9.7 Average Rating
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At the Hampton Terrace Bed and Breakfast Inn in Massachusetts, guests can relax and take advantage of the many amenities available. Each room is uniquely styled and features free Wi-Fi access and a TV, with decor that includes antique furnishings and plush bedding. An en suite bathroom and assorted amenities are also included.

In addition to the comfortable rooms, guests can enjoy a gourmet breakfast on the sun porch or dining room. Relax even further by the living room fireplace, listening to the grand piano sounds. The outdoor pool and on-site tennis courts are also available for use. And for those who want to explore the area, the Tanglewood Musical Center is only 5 minutes’ drive away.

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