The Berkshires combine outdoor recreation, the arts, and New England charm into a small, year-round getaway.
From calm hiking and foliage drives to Tanglewood performances and MASS MoCA, tourists come for the culture and scenery, and they remain for cozy accommodations that suit all types of travelers.
This article emphasizes the best places to stay in the Berkshires and directs you to the best hotels in the Berkshires for a variety of budgets and moods, whether you’re looking for luxurious service, fun for the whole family, or a comfortable inn near galleries and farm-to-table restaurants.
Top Hotels in the Berkshires (+ Resorts)
The Wheatleigh (Lenox) — If you’re searching for true luxury hotels Berkshires, The Wheatleigh is an immediate candidate. A historic estate turned intimate, high-service retreat with refined rooms, fine dining, and sweeping grounds that feel private yet central to Lenox’s cultural attractions.
Blantyre (Lenox) — A storied country-house hotel with old-world charm, Blantyre pairs classic service and sweeping lawns. It’s one of the Berkshires’ celebrated properties for travelers who relish atmosphere as much as comfort.
Cranwell Resort, Spa & Golf Club (Lenox) — Cranwell blends resort amenities with a stately New England setting. Great for travelers who want pools, spa services, and golf nearby. It’s often listed among the best resorts in the Berkshires for multi-activity stays.
Travelers who enjoy resort-style stays might also consider the best hotels in the Dolomites for a mountain retreat or the best place to stay in Algarve for a sunny coastal escape.
Canyon Ranch Lenox — For wellness-minded visitors, Canyon Ranch is a top choice among the best resorts in the Berkshires, offering structured health programs, fitness options, and restorative spa treatment in a serene setting.
The Red Lion Inn (Stockbridge) — For classic New England charm, this historic inn provides cozy rooms and a lively village atmosphere. Perfect if you want to be steps from museums, eateries, and seasonal events.
The Porches Inn at Mass MoCA (North Adams) — Bright, modern, and artsy, The Porches puts you within walking distance of MASS MoCA and galleries, making it one of the best places to stay in the Berkshires for art lovers and weekend culture trips.
Jiminy Peak Mountain Resort (Hancock) — If you’re traveling with family, Jiminy Peak serves as an ideal family resort Berkshires option. Ski-in/ski-out in winter, lift rides and summer activities for kids, with lodging that welcomes families and active groups.
Outdoor enthusiasts will love other scenic getaways too, like the best places to stay in the Smoky Mountains.
Best Western Plus Berkshire Hills Inn & Suites — A dependable mid-range pick, Best Western Plus Berkshire Hills Inn & Suites offers straightforward comforts and good access to Pittsfield and Lenox, ideal for budget-minded travelers who want a convenient home base.
Conclusion
The speed and aim of your trip will determine where you stay in the Berkshires.
If you want to be close to the culture, choose central inns, family resorts, or luxury hotels for quiet and pampering.
Regardless of the time of year, these choices—which include wellness centers, historic inns, and useful chains—represent some of the best hotels in the Berkshires and the greatest locations to stay for enjoyable, well-paced trips.