Photo by Photo courtesy of Berkshire Visitors Bureau

Luxury Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Luxury Hotels

Tonight
Nov 22 - Nov 23
Tomorrow
Nov 23 - Nov 24
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Top The Berkshires Luxury Hotels

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

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 P22,474
P27,187 total
includes taxes & fees
Dec 7 - Dec 8
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Terrace/patio
The Orchards Hotel

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
Gazebo
Lantern House Motel

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
Property grounds
Wagon Wheel Inn

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.
The price is P4,060
P4,535 total
includes taxes & fees
Nov 24 - Nov 25
Wagon Wheel Inn
Front of property - evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
  • Concierge services
9.6 out of 10, Exceptional, (799)
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 P7,849
P8,768 total
includes taxes & fees
Dec 22 - Dec 23
Hotel On North
Miscellaneous
1896 House Country Inn & Motels

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
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Hot tub
  • Indoor pool
  • Concierge services
9.2 out of 10, Wonderful, (1007)
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.
The price is P4,366
P4,877 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
Seasonal outdoor pool
Sunset Inn

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.
The price is P5,296
P5,916 total
includes taxes & fees
Dec 2 - Dec 3
Sunset Inn
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
  • Concierge services
9.6 out of 10, Exceptional, (585)
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 P5,826
P6,507 total
includes taxes & fees
Nov 24 - Nov 25
Maple Terrace Motel
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (825)
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.
The price is P4,649
P5,192 total
includes taxes & fees
Nov 24 - Nov 25
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.
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Top The Berkshires Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"All the design elements are wonderful! I enjoyed the room and the beautiful view of the town and the mountains. So clean and so spacious!! The staff - not so much, but everything else great."
Susie 2-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel

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