Ski Week in Monterey, MA: Houses for a Small Group
First, a point of order that saves some people a plane ticket: the Monterey with skiing is the one in the southern Berkshires of Massachusetts, a small hill town near Lake Garfield, not the one on the California coast. If you've landed here after reading about Pacific Grove and gray whales, you want the other search. If you're coming for Butternut and a woodstove, you're in the right place, and we manage five houses in this town. For a group of four to eight in January, the ones to compare are Scribe's Stable, Misty Pines Cabin, Forest Hollow, Bidwell Landing and Garfield Grounds. Nightly rates move around with the calendar, so the only honest way to test a $250 to $400 budget is to put your January dates into each listing and read the total with taxes and fees attached.
Where Monterey actually sits relative to the snow
Monterey is a wooded town about 15 minutes drive from Ski Butternut from our listings, and a bit over half an hour from Catamount. Great Barrington and the Mahaiwe sit roughly twenty minutes west, which is where you'll end up for dinner and a film. Beartown State Forest is on Monterey's doorstep, and in winter its roads and trails are where people walk off a big lunch rather than ski.
That geography shapes the trip more than any amenity does. You are not staying at the base of a mountain with a gondola out the window. You're staying in the woods, driving fifteen minutes to the lifts, and coming back to a house with a kitchen and a fire. People who want slopeside convenience should know that in advance. People who want the house to be the point of the week are in exactly the right town.
The five houses, in the order a small group should look at them
All five are single-family homes in Monterey, all have heating, Wi-Fi and free parking, and all are cleaned and inspected before you arrive with linens, towels and at least a morning's coffee waiting. Past that, they're genuinely different animals.
Scribe's Stable — 2 bedrooms, sleeps 6. A renovated barn with vaulted ceilings and exposed beams, and a kitchenette rather than a full kitchen. Dog friendly
Forest Hollow — 3 bedrooms, sleeps 6. On the water, with a woodstove and a fireplace, a full kitchen, and one and a half bathrooms. Dog friendly
Misty Pines Cabin — 3 bedrooms, sleeps 8, three bathrooms. Woodstove, indoor fireplace, firepit, and an outdoor wood-fired sauna. Dog-friendly, up to two.
Bidwell Landing — 4 bedrooms, 4 bathrooms, sleeps 8, on Lake Garfield with decks on multiple levels. No pets
Garfield Grounds — 4 bedrooms, sleeps 10 in season, lakefront, with a basement TV room and a jacuzzi tub. Pet friendly. Read the winter note below before you count beds.
Six people, and the bathroom question nobody asks until it's too late
Three of our Monterey houses sleep six, and the difference between them is not square footage, it's plumbing and cooking.
Scribe's Stable is a barn conversion with a king in one room and a queen plus twin bunks in the other, which makes it tidy for two couples or a family of four to six. It has one bathroom and a kitchenette with a mini fridge and a microwave, so six people who intend to cook a proper dinner every night will feel it. Six people who intend to ski, eat in Great Barrington and come back to read by the fire will not. It's two or three minutes by car to the Lake Garfield town beach, and the barn shares more than an acre with the owner's house next door, which is worth knowing if you want total seclusion.
Forest Hollow solves the cooking problem and keeps the bathroom one. Full kitchen, dining table, dishwasher, woodstove and a fireplace, with a queen, a double and two singles across three bedrooms, and one and a half baths. Our own description of it is the most January sentence in the portfolio: unwind by the fireplace after a day of skiing. That's the house. Its kayaks and dock belong to July, not to the week you're booking.
If six of you want three bedrooms, three bathrooms and a sauna, skip to Misty Pines.
The case for Misty Pines in winter specifically
Of everything we manage in Monterey, this is the house built for the month you're asking about. Three bedrooms and three bathrooms for up to eight, a woodstove and an indoor fireplace, a firepit and an outdoor fireplace, and an outdoor wood-fired sauna that you heat yourself and sit in while the pines keep things serene. Thirteen minutes to Ski Butternut per the listing, nine to Beartown State Forest. The third bedroom is four twins, which is a bunkroom in all but name and sorts out a group of friends or kids without anyone drawing straws over the sofa.
It's also the Monterey house guests rate most highly, across forty-one reviews, and it's pet friendly. If your January trip involves wet gear, a long afternoon on the hill and a desire to be warm afterwards, book this one and stop reading.
Four bedrooms: Bidwell Landing or Garfield Grounds
Both sit on Lake Garfield, both sleep eight or more on paper, and in January they behave very differently.
Bidwell Landing is four bedrooms and four bathrooms for eight, which is the most generous bathroom-to-person ratio in the town, and it matters at eight in the morning when everyone wants to be on the first chair. Two kings, a queen and two fulls. Pine forest around it, decks stacked on multiple levels, a dock below, and a hundred and seventy reviews behind it. No pets, no exceptions, so a group traveling with a dog should look elsewhere on this page.
Garfield Grounds is the biggest footprint of the five, with an open main floor, a basement TV room, a fireplace, a woodstove and a jacuzzi tub. Here's the thing a January booker must know: the separate guest cottage, which is counted as the fourth bedroom and sleeps two, is winterised and shut down from roughly late autumn until Memorial Day. It's included in bookings from Memorial Day weekend through Columbus Day weekend only. So the summer capacity of ten is not your January capacity. Count the main house beds, confirm the current configuration on the property page for your dates, and size the group to that.
Making a $250 to $400 night actually work
Our published rates across the portfolio run from the high one hundreds to the low seven hundreds a night before taxes and fees, so your range is real in Monterey, but it depends entirely on which house, which nights and how long you stay. A few things that move the number in your favour:
Midweek in January. Weekends and holiday weeks carry the most demand. A Monday-to-Thursday ski block is a different price conversation from a Friday arrival.
Read the total, not the headline. Taxes and the cleaning fee land at checkout. The cleaning fee goes directly to the person who cleans your house, in full, and we pay above the living wage, so it is not a padded line item.
Price per person, not per house. Eight people in Misty Pines or Bidwell Landing can land under a number that six in a smaller house cannot. Fitting the group to the beds is the single biggest lever you have.
Cook at least half your dinners. Four of these five have full kitchens with a dishwasher, which is where a ski week quietly saves or spends several hundred dollars.
Dogs. Four of the five take them for a one-time fee, with a cap on numbers. Bidwell Landing does not.
The winter driving part, which is not optional
Every one of our Monterey houses sits on a gravel or dirt road and driveway. We ask guests to arrive in an all-wheel-drive car in the winter months, and we mean it rather than suggest it. This is a hill town, the roads ice, and a rear-wheel-drive sedan loaded with four people and ski bags is how a Friday evening goes wrong. Driveway parking is finite too: three cars at Bidwell Landing, two at Scribe's Stable and Forest Hollow, multiple at Misty Pines and Garfield Grounds. Plan who's driving before you book, not after.
Our team is local and reachable from nine in the morning until nine at night, every day, which is the number that matters when the snow comes in overnight and you have a question about the road.
What to do on the day nobody wants to ski
There's always one. Beartown State Forest is minutes away and good for a cold walk. The Bidwell House Museum sits in Monterey itself for local history, and Great Barrington, about twenty minutes out, is where you'll find the Mahaiwe for a show and the W.E.B. Du Bois National Historic Site a little further along. The Norman Rockwell Museum is a little under half an hour.
How to book this
Pick the house by group size and by how you intend to spend the evenings, then put your dates in. Six who'll eat out: Scribe's Stable. Six who'll cook and want a fire: Forest Hollow. Eight who want bathrooms and a sauna: Misty Pines. Eight who want four bathrooms and a lake view: Bidwell Landing. A larger group that doesn't need the cottage: Garfield Grounds. Rates and availability for January live on each property page, and the total with taxes and fees appears before you commit.