Berkshire accommodation divides into four fairly distinct types, and choosing badly between them is the most common way to make a trip more expensive and less convenient than it needed to be.
The county has no large hotels in the conventional sense. What it has instead is a great many small properties, which means availability rather than price is often the binding constraint at peak times.
The four types
Country inns and bed-and-breakfasts are the classic Berkshire lodging: converted houses, often historic, usually with fewer than twenty rooms, generally including breakfast. They cluster around the southern towns — Lenox, Stockbridge, Great Barrington — and around Williamstown in the north.
They suit couples and adults travelling for the cultural season. They suit families with young children considerably less well, and a number decline children under a certain age outright.
Motels along the main routes are the least fashionable option and frequently the most sensible. They cost a fraction of an inn, they take families without fuss, they have parking at the door — which matters when unloading ski equipment — and they are perfectly comfortable. For a ski weekend where the room is used for sleeping and nothing else, this is usually the right answer.
Slopeside condominiums and suites at the ski areas put a party within walking distance of the lifts. The convenience is real: no driving in the dark on winter roads, no unloading at a distant lot, and the ability to go back to the room at lunchtime. They are correspondingly priced. Details on what those properties typically offer are on country inn and vacation home rentals.
Vacation houses are the answer for a group. A house sleeping eight or twelve costs less per head than four inn rooms, has a kitchen — which matters a great deal in a county where dining ends early — and gives a family reunion or a group of friends somewhere to be together in the evening.
How the calendar drives price
The Berkshires have two peak seasons and two dead ones, and rates swing sharply between them.
Summer, from late June to early September, is the highest. Tanglewood weekends in particular fill accommodation across a wide radius, and a room booked late for one of those is expensive and far away. Anyone planning a summer trip should check the performance calendar before assuming a date is ordinary — see cultural attractions.
Autumn foliage, roughly the first three weeks of October, is the sharpest peak of all and the shortest. Two-night minimums are usual and rates are at their annual high.
Winter is weekend-weighted rather than uniformly high. Saturday nights in ski season cost considerably more than Sundays through Thursdays, and holiday weeks price like summer.
November, and April into May, are the cheap months. A good deal is closed, but the museums are open and quiet, and rates are half what they are in August.
Two-night minimums on weekends are common year-round and near-universal at peak. Anyone wanting a single Saturday night should expect either to fail or to pay for two.
Where to base
This is worth deciding by activity rather than by which property looks nicest.
For skiing, base close to the hill. Winter roads in the dark are the reason — a twenty-minute drive each way in good conditions becomes forty in poor ones, and it happens twice a day. Slopeside or the nearest town.
For the cultural season, base in the south around Lenox and Stockbridge if the plan centres on Tanglewood and the Rockwell museum, or in Williamstown if it centres on the Clark and MASS MoCA. The two ends of the county are an hour apart and splitting the difference means driving through the middle every day.
For the outdoors, base wherever is convenient and accept the driving, since trailheads are spread throughout — see outdoors.
For a mixed group, a house is almost always right, and its location matters less than its size.
Practical points
Book earlier than feels necessary for summer and for October. The stock is small and it goes.
Check whether breakfast is included; at inns it usually is, and it changes the effective price meaningfully.
Check parking for a ski trip. A property with parking at the door is worth more in February than one with a lot two hundred yards away.
Ask about children before booking an inn rather than after.
Consider a kitchen. Dining in the county ends earlier than city visitors expect, and a group that arrives at nine on a Friday will be glad of one — see restaurants.
Getting to any of it requires a car, for reasons set out on getting here.