[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 Best Stockbridge Boutique Hotels

 

1. Wheatleigh

9.8 Average Rating
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The Wheatleigh is an exquisite chateau located in Lenox, Massachusetts, surrounded by 22 acres of the Berkshire Mountains. It features free Wi-Fi, wine tastings, and luxurious guest rooms with plush bedding and a flat-screen TV. Guests can also enjoy various amenities, such as 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 offer a fireplace and courtyard views or a seating area. They also feature an en suite bathroom with an antique soaking tub and a large shower.

The Wheatleigh is the perfect destination for a luxurious getaway.

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2. Life House, Berkshires

8.0 Average Rating
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Life House, Berkshires is a 4-star hotel in Lenox, 5.4 km from Tanglewood. It offers accommodation with a shared lounge, free private parking, a restaurant, and a bar. Free WiFi is also available.

The hotel’s non-smoking rooms have a desk, a flat-screen TV, a private bathroom, bed linen, and towels.

A continental breakfast is served each morning. The reception is available 24/7, with staff speaking English, Spanish, and French.

Nearby attractions include 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 located in Stockbridge, Massachusetts, set on 12 acres of land less than 3.2 km from Berkshire Theatre Festival. It offers stylish rooms with en suite bathrooms and a number of amenities for guests.

Each room is individually styled and has a flat-screen LCD TV and a bottle of sherry. Many of the rooms include a seating area with a gas fireplace.

The inn provides a number 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.

Guests can also 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 10 minutes’ 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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The Red Lion Inn is a historic boutique hotel in the heart of Stockbridge, Massachusetts. It 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 restaurants, The Main Dining Room, and Widow Bingham’s Tavern, serve classic American cuisine.

The Red Lion Inn is conveniently located near many attractions. The Norman Rockwell Museum, historic homes, antique shops, boutiques, and beautiful gardens are all within easy reach. Guests will find plenty of activities to enjoy in the area.

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5. The Cottage

7.1 Average Rating
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The Cottage is a Bed & Breakfast located in Stockbridge, Massachusetts. It sits on two acres of hills and forest and provides guests with stunning views of the Berkshire mountains. The Stockbridge town center is only 2 km away.

Each suite at The Cottage has a cable TV, a seating area with a sofa, a small refrigerator, a microwave, and a coffee maker. En-suite bathrooms are also included and provide guests with complimentary toiletries.

The Cottage provides guests with a private entrance to their suite and an outdoor patio with a dining area. There is also an on-site terrace and garden for added relaxation.

The Norman Rockwell Museum, Stockbridge Golf Club, and the Tanglewood Music Festival are all 3 km from The Cottage. Butternut Ski Resort and Bousquet Ski Area are less than 16 km away, and Jiminy Peak Mountain Resort is 38.3 km away. Mount Greylock is 45 km from The Cottage.

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6. Stockbridge Country Inn

9.3 Average Rating
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Stockbridge Country Inn is 1.5 km from Norman Rockwell and 1 km from Chesterwood Museums at Stockbridge. Tanglewood Music Center is 8.9 km away, and Ski Butternut is 14.7 km away. The Stockbridge Golf Course is 2.2 km from the inn.

The inn is nestled on 4 private acres of Berkshire landscape, offering guests various amenities. Each guestroom is appointed with a private en suite bath with full bath amenities, including cotton robes. Free WiFi access is also available.

In addition, guests can enjoy a gourmet country-style breakfast daily. Breakfast items include 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.

The boutique hotel 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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The Black Swan Lee – Lenox Ascend Hotel Collection is conveniently located in the foothills of the Berkshire Mountains. It 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, and Ski Butternut is a short distance away. The Lee Premium Outlets are perfect 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 guests can enjoy amenities like free wireless high-speed Internet access and local calls. All guest rooms are non-smoking and are equipped with refrigerators, Keurig coffee makers, hair dryers, irons, ironing boards, desks, and cable TV. Some rooms even feature balconies and whirlpool bathtubs.

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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. The boutique hotel 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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