Fall Season in Western Massachusetts

Find luxury hotels in Western Massachusetts, MA

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check availability on Western Massachusetts Luxury Hotels

Our top choices for Western Massachusetts luxury hotels

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
The price is £527
includes taxes & fees
16 Jun - 17 Jun
33 Main

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (631 reviews)
The price is £274
includes taxes & fees
5 Jul - 6 Jul
The Williams Inn

MGM Springfield

MGM Springfield
4.0 star property
Metro Center
9.0 out of 10, Wonderful, (1,552 reviews)
The price is £194
includes taxes & fees
23 Jun - 24 Jun
MGM Springfield

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
The price is £327
includes taxes & fees
23 Jun - 24 Jun
The Inn at Stockbridge

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, (111 reviews)
  • cleanliness
    Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
The price is £298
includes taxes & fees
29 Jun - 30 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
The price is £297
includes taxes & fees
16 Jun - 17 Jun
The Old Inn On The Green

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
The price is £282
includes taxes & fees
16 Jun - 17 Jun
Devonfield Inn B&B

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (370 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
The price is £101
includes taxes & fees
29 Jun - 30 Jun
The Central Downtown Inn & Suites

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
The price is £182
includes taxes & fees
16 Jun - 17 Jun
Hampton Terrace Inn

Troutbeck

Troutbeck
5.0 star property
Amenia
10.0 out of 10, Exceptional, (1 review)
The price is £502
includes taxes & fees
21 Jun - 22 Jun
Troutbeck
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 Western Massachusetts

Western Massachusettsand its attractions for luxury travelers

Western Massachusetts is a paradise for luxury travellers seeking both adventure and tranquillity. Begin your exploration in the charming town of Lenox, home to the renowned Tanglewood Music Center, where you can enjoy enchanting summer concerts amidst stunning natural scenery. Then, immerse yourself in the beauty of the Norman Rockwell Museum in Stockbridge, showcasing the iconic artist's work and offering a glimpse into classic Americana. For outdoor enthusiasts, the breathtaking landscapes of the Berkshires are perfect for hiking and cycling, with trails that offer both challenge and stunning vistas. Golf aficionados can indulge at the prestigious Cranwell Spa & Golf Resort, which combines a world-class course with exquisite spa services. Lastly, unwind in the cultural hub of Northampton, known for its eclectic shops and vibrant arts scene, where you can experience fine dining at upscale restaurants. For a luxurious stay, consider the historic Wheatleigh Hotel in Lenox, where opulent rooms and impeccable service set the stage for an unforgettable retreat. Each experience in Western Massachusetts is designed to pamper and delight, ensuring that your every need is met and your adventures are as enriching as they are relaxing.

Top Western Massachusetts Hotel Reviews

Explore a world of travel with Expedia