Where to stay in the Berkshires: the 4 areas to know in 2026
In the Berkshires, the season chooses for you. In summer, everything revolves around Lenox and the Tanglewood concerts. In October, the colours and the great museums pull you north, to Williamstown. And all year round, the south, from Stockbridge to Great Barrington, keeps the prettiest villages and the best tables.
Clean motels start at $124*, a village inn in an old wooden house often costs $290* a night in season, and the great Gilded Age estates go beyond $680*. The four areas below are only half an hour apart.
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One base or several?
The region can be crossed in an hour: a single base is enough for a weekend. For a week, better to take two, one in the south and one in the north.
- A weekend: A single base, in Lenox or Stockbridge: a concert, the Rockwell museum and a Gilded Age mansion.
- Four or five days: A single base, in Stockbridge or Great Barrington, with a day in the north for Mass MoCA and the Clark.
- One week: Two bases: four nights in the south, around Lenox or Stockbridge, then three in Williamstown.
How much driving between two bases?
Times given by car, outside concert nights. Route 7 links every area from north to south.
| Route | Driving time | Good to know |
|---|---|---|
| Boston → Lenox | 2 hr 30 | via I-90 |
| New York → Great Barrington | 2 hr 45 | via the Taconic Parkway |
| Albany airport → Pittsfield | 1 hr | via US 20 |
| Great Barrington → Stockbridge | 15 min | via Route 7 |
| Stockbridge → Lenox | 15 min | via Route 7 |
| Lenox → Pittsfield | 15 min | via Route 7 |
| Pittsfield → Williamstown | 35 min | via Route 7 |
| Williamstown → North Adams | 10 min | via Route 2 |
At a glance: our picks by traveller type
Pick the profile that fits you and go straight to the recommended area.
Map of the areas in the Berkshires
See how the areas sit relative to one another before choosing your base. Click a name to jump to its description.
Lenox and Lee Lenox, Lee, Becket and Richmond, around Tanglewood
for the summer festivals and the Gilded Age mansions
The heart of summer. Lenox lines up its galleries, restaurants and great Gilded Age mansions, and the Tanglewood concerts are five minutes away. Shakespeare and Company performs outdoors, and Jacob's Pillow dances in the woods of Becket. Lee, more modest, keeps gentler prices and its outlet shops. The downside: rates soar on concert nights, and the roads fill up.
Where to stay in this area
Courtyard by Marriott Lenox Berkshires Mid-range
A modern, practical hotel between Lenox and Lee, a few minutes from Tanglewood and Route 7.
Pros
- Tanglewood five minutes away
- Restaurants and galleries on foot
Cons
- The highest prices in July
- Busy roads on concert nights
Stockbridge and Great Barrington Stockbridge, West Stockbridge, Great Barrington, Sheffield, Egremont and the southern hills
for postcard villages and the best tables
The south of the Berkshires, the liveliest all year round. Stockbridge is the main street Norman Rockwell painted, with its grand porched inn. Great Barrington, fifteen minutes away, has the best restaurants, the shops and the area's two ski resorts. Further south, Sheffield and Egremont live to the rhythm of farms and antique dealers. The downside: Williamstown and its museums are an hour away.
Where to stay in this area
The Red Lion Inn Mid-range
The great inn on Main Street in Stockbridge, with its porch of rocking chairs, open since the 18th century.
Granville House Mid-range
A beautifully kept guest house in Great Barrington, a few minutes from the restaurants in the centre.
Quality Inn Great Barrington city.oudormir_tier_economique
Simple, spacious rooms with breakfast, within walking distance of the restaurants and shops.
Pros
- The prettiest villages and the best tables
- A lively base in every season
Cons
- The northern museums an hour away
- Inns fully booked in October
Pittsfield and the centre Pittsfield, Dalton, Lanesborough, Hancock and the central hills
for gentler prices, the Shakers and Melville
The only real city in the Berkshires, at the crossroads of every road. Pittsfield has its theatre, its breweries and its restored main street, and the Shaker village at Hancock is ten minutes away. Arrowhead, Melville's house, looks out at Greylock. The downside: less charm than the villages, but rooms often cheaper in summer.
Where to stay in this area
Hotel on North Mid-range
A characterful hotel in two brick buildings on North Street, in the heart of Pittsfield.
Pros
- At the centre of the whole region
- Gentler prices than Lenox
Cons
- A city less charming than the villages
- Few inns with character
Williamstown and North Adams Williamstown, North Adams, Adams and the foot of Mount Greylock
for the art museums, Greylock and the autumn colours
The north of the Berkshires, the museum north. Williamstown, a college town with immaculate lawns, is home to the Clark and its grounds. Ten minutes away, North Adams turned a huge textile mill into the Mass MoCA museum. Mount Greylock towers over both. The downside: Tanglewood and Stockbridge are nearly an hour away.
Where to stay in this area
The Williams Inn Luxury
A new, light-filled hotel in the centre of Williamstown, within walking distance of the campus and the Clark.
Tourists Mid-range
A reinvented old roadside motel, with a pool, gardens and forest trails, five minutes from Mass MoCA.
Maple Terrace Motel city.oudormir_tier_economique
A small, well-kept family motel at the entrance to Williamstown, a few minutes from the centre.
Pros
- The region's two biggest museums
- Greylock and its trails on the doorstep
Cons
- Tanglewood nearly an hour away
- Little going on in the evening outside term time
Our tips for booking the right place
- Book October in summer: In the first two weeks of October, every inn is full at weekends, often with a two-night minimum. Book in July, or come midweek: you will pay less and find room.
- Check the Tanglewood calendar: On big concert nights, rooms in Lenox double in price and the roads jam. If you are not coming for the music, avoid those dates, or stay in Great Barrington or Pittsfield.
- Try a village inn: Old wooden houses turned into inns are the experience of the region: home-made breakfast, a fireplace and hosts who know every trail. They have few rooms: book early.
- Staying in Boston or New York for a day trip: three hours on the road each way.
- Taking a single base in the north for Tanglewood: the drive back at night after the concert takes nearly an hour.
- Arriving in April without checking: many inns and restaurants close between the snow and the summer.
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