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Top The Berkshires Luxury Hotels

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
  • Concierge services
9.2 out of 10, Wonderful, (110)
Mountain serenity defines this luxury Stockbridge retreat, featuring a seasonal outdoor pool surrounded by sun loungers and lush gardens. Personal chef service, complimentary gourmet breakfast, and concierge attention create a pampered experience minutes from cultural landmarks.
$414 nightly
The price is $462
Dec 14 - Dec 15
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Orchards Hotel

2.5 star property
Williamstown
  • Concierge services
8.6 out of 10, Excellent, (442)
Sophisticated relaxation awaits at this mountain hotel. Guests savor complimentary continental breakfast before lounging by the seasonal outdoor pool. Plush bathrobes, designer toiletries, and massage services create an indulgent experience amid natural beauty.
The Orchards Hotel

Lantern House Motel

2.5 star property
Great Barrington
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
8.2 out of 10, Very Good, (455)
Mountain views frame this tranquil Great Barrington getaway where a seasonal outdoor pool invites refreshing dips after exploring nearby attractions. Garden spaces and picnic areas create perfect relaxation spots following adventures at Monument Mountain Reservation or performances at Mahaiwe Arts Center.
Lantern House Motel

Wagon Wheel Inn

2.0 star property
Lenox
  • Hot tub
7.0 out of 10, Good, (641)
Soak in the clean, spacious hot tub after exploring nearby Tanglewood Music Center. This conveniently located Lenox retreat offers air-conditioned rooms with refrigerators and microwaves, while helpful staff ensure a comfortable, pampered stay near ski areas and historic towns.
$69 nightly
The price is $77
Dec 2 - Dec 3
Total with taxes and fees
Wagon Wheel Inn

Hotel On North

3.5 star property
Pittsfield
  • Concierge services
9.6 out of 10, Exceptional, (801)
Sophisticated comfort defines this beautifully decorated Pittsfield retreat. Spacious, elegantly appointed rooms feature plush bedding and premium amenities, while the on-site restaurant serves excellent cuisine. Concierge services anticipate every need, creating a luxurious mountain getaway experience.
$133 nightly
The price is $149
Dec 22 - Dec 23
Total with taxes and fees
Hotel On North

1896 House Country Inn & Motels

2.5 star property
Williamstown
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
  • Business services
  • Bar
6.6 out of 10, (448)
Surrounded by gardens, this elegant inn blends historic character with exceptional comfort. Fine dining and handcrafted drinks await in the restaurant and bar, while the tranquil grounds offer a perfect retreat after exploring nearby cultural attractions.
$113 nightly
The price is $127
Dec 2 - Dec 3
Total with taxes and fees
1896 House Country Inn & Motels

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Hot tub
  • Indoor pool
  • Concierge services
9.2 out of 10, Wonderful, (1013)
Luxurious relaxation permeates this Berkshires sanctuary featuring indoor and outdoor pools complemented by a rejuvenating hot tub. Spacious rooms showcase mountain panoramas, while attentive concierge services elevate each stay. Just minutes from Tanglewood and premier skiing.
$63 nightly
The price is $70
Dec 14 - Dec 15
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Sunset Inn

2.0 star property
Lee
  • Near the beach
7.6 out of 10, Good, (410)
Luxurious simplicity defines this Berkshire retreat near Tanglewood Music Center. Nestled in a quiet location within walking distance to local attractions, this motel combines spotless rooms, a refreshing seasonal pool, and attentive service for a serene escape.
$86 nightly
The price is $97
Dec 5 - Dec 6
Total with taxes and fees
Sunset Inn

Maple Terrace Motel

2.5 star property
Williamstown
  • Concierge services
9.6 out of 10, Exceptional, (586)
Sophisticated relaxation defines this immaculate Williamstown retreat. Pristine gardens surround a crystal-clear seasonal pool where sun loungers invite leisurely afternoons. Individually decorated rooms feature thoughtful amenities, while concierge services ensure every luxury need is promptly fulfilled.
$99 nightly
The price is $111
Dec 2 - Dec 3
Total with taxes and fees
Maple Terrace Motel

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (827)
Hydromassage showers and deep soaking bathtubs elevate the experience at this tranquil Lenox haven. Garden views complement the refreshing outdoor pool, while spotless rooms provide a comfortable sanctuary after exploring nearby Tanglewood Music Center.
$79 nightly
The price is $88
Dec 2 - Dec 3
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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Find out more about The Berkshires

The Berkshiresand its attractions for luxury travelers

The Berkshires, a picturesque region in Massachusetts, offers luxury travelers an exquisite blend of culture, nature, and relaxation. Begin your journey at the renowned Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class performances in a stunning outdoor setting. For art enthusiasts, the Massachusetts Museum of Contemporary Art (MASS MoCA) is a must-visit, showcasing innovative installations and a vibrant arts scene. Nature lovers will revel in the serene beauty of the Bershires' rolling hills, perfect for hiking and exploring the Appalachian Trail, while the enchanting gardens at Naumkeag provide a peaceful retreat. After a day of adventure, unwind at the historic Wheatleigh Hotel, where luxurious accommodations and fine dining await, providing an ideal base to explore the region's charm. With attentive service and upscale amenities, your experience in The Berkshires is sure to be both memorable and rejuvenating.

Top The Berkshires Hotel Reviews

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