Top 11 Luxury Hotels In The Berkshires, Massachusetts - Updated 2023

| 5 min read

The Berkshires is one of the most luxurious vacation destinations you can find in Massachusetts. Located in the scenic Green Mountains, this idyllic mountainside area is home to some of the region’s best luxury hotels. If you’re looking for a relaxing natural retreat, the glamping spots in the Berkshires are one of the best venues for a peaceful time. Aside from the majestic mountainscapes, you can also enjoy a variety of outdoor activities such as hiking, water sports, and camping. For winter adventures, the ski resorts in the Berkshires are the go-to spots. Catch any one of its seasonal festivals, such as the Boston Symphony Orchestra’s residency held at Lenox’s Tanglewood Music Centre. Wondering where to stay in the Berkshires? A multitude of charming inns and hotels are ready to help make your stay unforgettable. Scroll down to see the list of top luxury hotels in the Berkshires, Massachusetts.

1. Seven Hills Inn (from USD 325)

In the middle of a fairytale-like forest is Seven Hills Inn — an elegant four-star hotel that’s perfect for your private getaway. Located in Lenox, Seven Hills Inn is a non-smoking property near Tanglewood Musical Centre. It has spacious rooms equipped with modern furnishings and comfortable beddings along with Wi-Fi, a cable TV, and a coffee machine. All rooms have an attached sun terrace where you can lounge and watch the sunset from your own private sanctuary. Guests can start their day off with a sumptuous breakfast at the on-site dining area before heading out for a day of outdoor activities in the Berkshires.

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Seven Hills Inn

Address: 40 Plunkett St, Lenox Dale, Lenox (MA), United States, MA 01240-2704
7.04 km (4.4 mi) from Norman Rockwell Museum

2. Wheatleigh (from USD 898)

If you’re looking for accommodation in Lenox that’s about the finer things in life, Wheatleigh fits the bill. This luxurious chateau will have you pampered in its rooms that feature seating areas with fireplaces and courtyard views. You’ll surely want to enjoy soothing soaks in the en suite shower room with an antique soaking tub. You can also head to the property’s massage room for more relaxing treatments.

Don’t miss out on deluxe amenities during your stay, such as the seasonal outdoor pool, wine tastings, and free perks such as Wi-Fi and parking. Maximize the on-site top-notch fitness center and tennis court if you wish to stay active on vacation.

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Wifi Available Wheelchair accessible

Address: 11 Hawthorne Road
6.53 km (4.1 mi) from Norman Rockwell Museum

Parking Restaurant Pets allowed Room service Meeting/banquet facilities Bar 24-hour front desk Tennis court

3. Hampton Terrace Inn (from USD 286)

This romantic bed and breakfast is one of the top choices for couples visiting the Berkshires. Every room at Hampton Terrace Inn is beautifully decorated with antique furnishings and plush beddings, and they come with free Wi-Fi and cable TV. After a day of pampering, relax in your private bathtub or enjoy an evening by the cosy living room fireplace. This luxury accommodation also allows guests to use the outdoor pool and on-site tennis courts during their stay. From here, you can easily reach Tanglewood Musical Centre and Mission House Museum and Gardens. Alternatively, hit the slopes at the Bousquet Mountain ski area during winter, which is 8 km (5 mi) away from Hampton Terrace Inn.

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Hampton Terrace Inn

Wifi Available

Address: 91 Walker St.
8.71 km (5.5 mi) from Norman Rockwell Museum

Parking Tennis court Garden Terrace Non-smoking rooms Skiing Free parking Internet services

4. The Red Lion Inn (from USD 208)

Located in the heart of central Stockbridge, the Red Lion Inn is a historic four-star luxury hotel. This charming hotel provides guests with convenient access to nearby attractions, which include Norman Rockwell Museum, local antique shops, boutiques, and gardens. Stay at this hotel to enjoy the combination of rustic charm and modern amenities, with fully equipped rooms and high-speed Wi-Fi across the property. On-site dining options offer a delectable selection of local cuisine — have dinner at Widow Bingham’s Tavern and grab a drink at The Lion’s Den. For those looking to rest and relax, you can use the year-round outdoor pool or even book a massage service at the hotel’s wellness spa.

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The Red Lion Inn

Wifi Available

Address: 30 Main Street
2.08 km (1.3 mi) from Norman Rockwell Museum

Parking Restaurant Pets allowed Meeting/banquet facilities Bar 24-hour front desk Fitness centre Golf course (within 3 km)

5. The Old Inn On The Green (from USD 494)

This gorgeous four-star property aptly named The Old Inn on the Green is located in New Marlborough. This gorgeous rustic hotel offers a daily English or Irish breakfast for their lucky guests. All rooms are furnished with charming antique decorations that will make you feel right at home. Necessary amenities such as air conditioning and free Wi-Fi are also available for guests’ convenience. Nature enthusiasts will be glad to know that the surrounding area offers hiking and walking trails that allow you to take in the beauty of the Berkshires.

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The Old Inn On The Green

Address: 134 Hartsville New Marlborough Road, New Marlborough, New Marlborough (MA), United States, 01230
20.32 km (12.7 mi) from Norman Rockwell Museum

Other luxury accommodations

6. Devonfield Inn (from USD 289)

Spanning over 30 acres (12 hectares) of private land, Devonfield Inn is a premium bed and breakfast that’s perfect for a romantic getaway. Its premises is impressively grand, you might think you’ve been whisked away to a luxury resort in the Berkshires upon entrance.

The luxurious accommodation features a variety of room types, including deluxe rooms, suites, rooms with fireplaces and whirlpool tubs, and even a penthouse suite. Guests can take a dip in the heated seasonal outdoor pool or play a game of tennis at the on-site courts. Devonfield Inn features ornate decor and antique furniture, making it a top choice for those who fancy this classic look. Another highlight of this bed and breakfast is the farm-to-table daily breakfast buffet that features fresh local produce and homemade baked delicacies.

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Devonfield Inn

Wifi Available

Address: 85 Stockbridge Rd.
6.1 km (3.8 mi) from Norman Rockwell Museum

Parking Meeting/banquet facilities Tennis court Fitness centre Golf course (within 3 km) Garden Terrace Non-smoking rooms

7. The Porches Inn at Mass MoCA (from USD 169)

This accommodation is tailor-made for those who love the arts. The Porches Inn is located just across the street from Massachusetts Museum of Contemporary Art (MoCA). This fashionable property even offers on-site art exhibitions, or you can take a 15-minute walk and find various New Adams art galleries as well. All rooms here were meticulously designed, featuring retro decor and brightly coloured furnishings. Free Wi-Fi is available across the property, where you will also find the fitness centre, sauna, and hot tub that’s free for use. The Porches Inn offers daily continental breakfast, as well as full bar service at the on-site Lobby Bar.

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The Porches Inn at Mass MoCA

Wifi Available

Address: 231 River Street.
49.54 km (30.8 mi) from Norman Rockwell Museum

Parking Pets allowed Room service Meeting/banquet facilities Bar 24-hour front desk Golf course (within 3 km) Garden

8. Vacation Village In The Berkshires (from USD 168)

If you want to stay close to the action, then the scenic Vacation Village In The Berkshires is the one for you. The accommodation is located mere steps away from a plethora of seasonal activities such as exciting biking trails, fishing, and swimming as well as historical sites and diverse dining options. The expansive property is hidden away in the picturesque countryside of the Berkshires, making it ideal for travellers who want some peace and quiet. Guests can also make use of the on-site amenities, such as the fitness centre and the large indoor and outdoor swimming pools. With panoramic glass windows surrounding the perimeter, the outdoor pool is the perfect spot to admire the sunset.

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Vacation Village in the Berkshires

Address: 276 Brodie Mountain Rd, Hancock, MA, USA, 01237
31.04 km (19.3 mi) from Norman Rockwell Museum

Paid WiFi Heating Indoor pool Table tennis Physical distancing rules followed Outdoor pool Heated pool 24-hour front desk

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9. Berkshire Mountain Lodge (from USD 165)

Berkshire Mountain Lodge, a luxurious mountainside inn, is a popular choice for holidaymakers who want a tranquil nature retreat. Hidden away among the lush greenery of the Berkshires, the lodge offers both convenience and privacy. All rooms come with the necessary amenities, such as a cable TV, free Wi-Fi, and a bathtub. On-site facilities include a year-round indoor swimming pool, a fitness centre, and a game room for your enjoyment. From the lodge, Berkshire Museum is a mere six-minute drive away.

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Berkshire Mountain Lodge

Wifi Available Wheelchair accessible

Address: 8 Dan Fox Drive
14.89 km (9.3 mi) from Norman Rockwell Museum

Parking Sauna Fitness centre Non-smoking rooms Laundry Facilities for disabled guests Skiing Family rooms

10. Shaker Mill Inn (from USD 195)

Shaker Mill Inn is one of the best luxury hotels in the Berkshires yet it feels like a home away from home. All rooms here are apartment-style suites that come with a private bathroom, a kitchen, a living area, and a bedroom. The suites are equipped with free Wi-Fi, air conditioning, TV access, a microwave, a fridge, an oven, a toaster, and a coffee machine for guests to use. A daily continental breakfast is also served on-site, ensuring you get a hearty meal before you set off for a day’s worth of activities. Located in West Stockbridge, the scenic area is also home to a wide variety of outdoor activities, such as hiking, skiing, and cycling.

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Shaker Mill Inn

Wifi Available

Address: 2 Oak Street
5.98 km (3.8 mi) from Norman Rockwell Museum

Parking Pets allowed Non-smoking rooms Fishing Skiing Breakfast in the room Free parking Internet services

11. 1896 House Inn and Country Lodgings (from USD 229)

Located in charming Williamstown, 1896 House Inn and Country Lodgings is a classic bed and breakfast that’s popular with couples. Rooms here feature antique furnishings and ornate designs, giving it a cosy and old-timey feel. The rooms also come equipped with a private hot tub in addition to all the necessary amenities, such as cable TV and even a fireplace. Guests can also use the outdoor pool or visit the on-site restaurant and bar where a range of local dishes are served for both lunch and dinner. This accommodation is a five-minute drive from Williams College and Clark Art Institute.

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1896 House Country Inn - Barnside Inn

Wifi Available Wheelchair accessible

Address: 910 Cold Spring Road
46.14 km (28.7 mi) from Norman Rockwell Museum

Parking Restaurant Pets allowed Room service Meeting/banquet facilities Bar Golf course (within 3 km) Garden

Rest and relax in the Berkshires

If you’re lucky enough to visit the picturesque Berkshires, picking a suitable accommodation is essential. A stay at any one of these best hotels in the Berkshires will be the highlight of your unforgettable trip, so make sure to choose wisely.

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Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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This talented writer is an enthusiastic solo traveler. She also seamlessly integrates her passion for both writing and photography into her creative pursuits.

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