Western Massachusetts Luxury Hotel

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Our top choices for Western Massachusetts luxury hotels

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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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is HK$2,972
HK$3,595 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is HK$3,228
HK$3,606 total
includes taxes & fees
14 Jan - 15 Jan 2026
33 Main
Front of property
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is HK$1,952
HK$2,290 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Inn at Stockbridge
Front of property – evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (549)
"Nice place to stay for a wedding "
United States
Timothy
The price is HK$1,473
HK$1,646 total
includes taxes & fees
21 Dec - 22 Dec
The Williams Inn
Breakfast, lunch, dinner served; American cuisine
The Old Inn On The Green

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is HK$2,374
HK$2,864 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Old Inn On The Green
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is HK$1,360
HK$1,596 total
includes taxes & fees
19 Dec - 20 Dec
Lakehouse Inn
8 restaurants, breakfast, lunch, dinner served; American cuisine
MGM Springfield

MGM Springfield

MGM Springfield
4.0 star property
Metro Center
9.0 out of 10, Wonderful, (1456)
"Great room, nice venue, with free self parking "
United States
Chuck
The price is HK$1,160
HK$1,492 total
includes taxes & fees
7 Jan - 8 Jan 2026
MGM Springfield
Balcony
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is HK$695
HK$776 total
includes taxes & fees
17 Dec - 18 Dec
The Central Downtown Inn & Suites
Exterior detail
Hampton Terrace Inn

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is HK$2,046
HK$2,285 total
includes taxes & fees
16 Jan - 17 Jan 2026
Hampton Terrace Inn
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 Western Massachusetts Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"This is a wonderful place to stay. The breakfast is delicious. The pool and hot tub are delightful. The staff are like family. "
Kathy 3-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

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