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Luxury Hotels & Resorts in The Berkshires from NZ$136

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Check availability on The Berkshires Luxury Hotels

Best 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.
The price is NZ$816
includes taxes & fees
7 Dec - 8 Dec
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 savour complimentary continental breakfast before lounging by the seasonal outdoor pool. Plush dressing gowns, 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 Centre.
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 spa pool after exploring nearby Tanglewood Music Centre. 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.
The price is NZ$136
includes taxes & fees
30 Nov - 1 Dec
Wagon Wheel Inn

Hotel On North

3.5 star property
Pittsfield
  • Concierge services
9.6 out of 10, Exceptional, (798)
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.
The price is NZ$265
includes taxes & fees
7 Dec - 8 Dec
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.
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, (1005)
Luxurious relaxation permeates this Berkshires sanctuary featuring indoor and outdoor pools complemented by a rejuvenating spa pool. Spacious rooms showcase mountain panoramas, while attentive concierge services elevate each stay. Just minutes from Tanglewood and premier skiing.
The price is NZ$153
includes taxes & fees
3 Dec - 4 Dec
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 Centre. 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.
The price is NZ$170
includes taxes & fees
2 Dec - 3 Dec
Sunset Inn

Maple Terrace Motel

2.5 star property
Williamstown
  • Concierge services
9.6 out of 10, Exceptional, (584)
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.
The price is NZ$195
includes taxes & fees
23 Nov - 24 Nov
Maple Terrace Motel

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (824)
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 Centre.
The price is NZ$151
includes taxes & fees
21 Nov - 22 Nov
Howard Johnson by Wyndham Lenox
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about The Berkshires

The Berkshiresand its attractions for luxury travelers

The Berkshires, a picturesque region in Massachusetts, offers a wealth of luxurious experiences for the discerning traveller. Begin your journey at Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class performances under the stars while surrounded by the stunning natural beauty of the Berkshire hills. For art enthusiasts, the Norman Rockwell Museum in Stockbridge showcases the beloved works of America’s favourite illustrator, providing a glimpse into the cultural heart of the region. Those seeking relaxation can indulge in the serene atmosphere of Canyon Ranch, a wellness resort that offers spa treatments, fitness classes, and gourmet dining focused on health and well-being. For outdoor adventurers, the expansive hiking trails at Mount Greylock State Reservation promise breathtaking views, particularly in autumn when the foliage is ablaze with colour. Finally, indulge your palate at the acclaimed restaurants in Lenox, where farm-to-table dining experiences await, featuring the best local and seasonal ingredients. For a truly luxurious stay, consider the enchanting bluestone buildings of the Wheatleigh Hotel, a former Gilded Age mansion, where attentive service and elegant rooms make for an unforgettable retreat.

Top The Berkshires Hotel Reviews

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