Pittsfield 4 Star Hotels In 2025

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Featured Pittsfield 4 Star Hotels

The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The Williams Inn
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
The Central Downtown Inn & Suites
Lakehouse Inn

Lakehouse Inn

4 out of 5
615 Laurel St., Lee, MA
Lakehouse Inn
33 Main

33 Main

4 out of 5
33 Main Street, Lenox, MA
33 Main
Seven Hills Inn

Seven Hills Inn

4 out of 5
40 Plunkett Street, Lenox, MA
Seven Hills Inn
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street, Lee, MA
The Inn at Stockbridge
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd., Lee, MA
Devonfield Inn B&B
Hampton Terrace Inn

Hampton Terrace Inn

4 out of 5
91 Walker Street, Lenox, MA
Hampton Terrace Inn
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 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
See all 1,358 properties in Pittsfield
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.

Four Star Hotel Guide for Pittsfield, Massachusetts

Over the years, you’ve pinched pennies and stayed at the economy motels during your travels. However, now you’re nearing retirement or already basking in the work-free lifestyle, and you deserve to treat yourself to four-star hotels for ARRP members and seniors in Pittsfield, Massachusetts. Known for their extra perks, first-rate service, and fantastic locations, each of our 4-star AARP hotels in Pittsfield offers the ultimate experience for those looking for a bit of glitz and glamour on vacation.

Relax in your expertly designed room, kick back with around-the-clock room service, and indulge in the first-class amenities. Receive a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all at your fingertips, when you stay at one of the Pittsfield hotels with 4 stars for AARP members. Whether you’re traveling to celebrate the birth of your first grandchild or vacationing because you finally have the free time, let Expedia and AARP’s joined forces provide you with the best rates around on AARP hotels with four stars.