Charming historic cottage on scenic road to Mt. Greylock
If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a guest house - since 1998.
PLEASE NOTE: It's an old building with an unusual layout, so please carefully read the description below.
Beautifully situated amidst horse farms on the scenic road to Mt Greylock. In the center of the Berkshires, 5 miles from Jiminy Peak ski area, 10 miles from South Williamstown, 15 miles from Tanglewood and Mass MoCA, and 20 miles from Jacob's Pillow. 5 miles to Pittsfield and the Berkshire Mall. Private garden. 5 acres of property in the back where horses graze, and alpacas, donkeys and other friendly animals next door.
Everything is provided: fully-furnished mostly with antiques. Bedspreads, linens, blankets, pillows, towels, iron and ironing board. SMALL KITCHEN with mini stove/oven, refrigerator, microwave, Keurig coffeemaker with assortment of coffee, tea and hot chocolate, pots and pans, dishes, cutlery, etc. Broadband internet and TV with Netflix, Hulu and other streaming options included.
There are 2 floors. The first floor is the old classroom with old desks. There is also a trundle bed which can be used as 2 twins. The bathroom is on the first floor. The 2nd floor is like a studio apartment - with a queen bed and a twin bed and the small kitchen. PLEASE NOTE: There is one bathroom, on first floor.
Ideal for a romantic getaway or for a family of 4-5. A fee of $25/night applies for additional adults after the first two (limit of 4 adults total). No extra charge for children. Please indicate the number of children in your message to us, but select 0 children in the pull-down menu so that you are not charged.
The Old Stone School is available to rent 12 months a year. Each season has it's benefits:
SPRING - Trees arise from winter sporing their fleeting Spring green color, daffodils, tulips, hiking trails are open, enjoy the warm weather after a long winter! Calves appear on the hill behind the schoolhouse.
SUMMER - Flowers blooming, berries to pick, outdoor activities nearby, culture everywhere - Tanglewood, Jacob's Pillow, Barrington Stage, Clark Art Museum, MassMoCA, Williams College Museum of Art, etc.
FALL - Enjoy the kaleidoscope of Fall colors covering the hills behind the schoolhouse. Hike Mt. Greylock - short and long hikes. Go the top and check out Bascom Lodge - a stop on the Appalachian Trail.
WINTER - Jiminy Peak is less than 10 mins. away.Ski or snow tube at Bousquet is 20 mins. away. Cross country Ski in the fields out back or go to Hilltop Orchards in Richmond or Notchview in Windsor.
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The host requires you to complete the following before checking out:
Remove personal items
Hang key up by the door
Failure to complete these may result in a negative review from the host.
We do not charge for children. Please indicate on
Important information
You need to know
Property Registration Number C0201341480
Property # 300900
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Lanesborough
Located in Lanesborough, this cottage is in a rural area and in the mountains. Mount Greylock State Reservation and Mount Greylock State Reservation Visitor Center reflect the area's natural beauty and area attractions include Mountain Coaster and Alpine Super Slide. Lichtenstein Center for the Arts and Berkshire Museum are also worth visiting. Discover the area's water adventures with nearby swimming, or enjoy the great outdoors with mountain climbing, hiking and mountain biking.
Mount Greylock State Reservation - 4 min drive - 2.2 km
Jiminy Peak Mountain Resort - 12 min drive - 10.7 km
Williams College - 21 min drive - 26.5 km
Tanglewood Music Center - 37 min drive - 29.0 km
National Shrine of the Divine Mercy - 47 min drive - 41.4 km
Getting around
Pittsfield Intermodal Transportation Center - 12 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 21 min drive
Restaurants
McDonald's - 12 min drive
Friendly's - 12 min drive
Cumberland Farms - 12 min drive
JJ's Lodge - 10 min drive
Old Man Jeff’s Barbecue Company - 11 min drive
Frequently asked questions
Is Charming historic cottage on scenic road to Mt. Greylock pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Charming historic cottage on scenic road to Mt. Greylock?
As of 14 May 2026, prices found for a 1-night stay for 2 adults at Charming historic cottage on scenic road to Mt. Greylock on 17 May 2026 start from NZ$448, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Charming historic cottage on scenic road to Mt. Greylock?
On-site parking is available at the property.
What time is check-in at Charming historic cottage on scenic road to Mt. Greylock?
Check-in begins at 3:00 PM.
What time is check-out at Charming historic cottage on scenic road to Mt. Greylock?
Checkout is at 11:00 AM.
Where is Charming historic cottage on scenic road to Mt. Greylock located?
Situated in the mountains, this cottage is 1 mi (1.6 km) from Mount Greylock State Reservation and within 3 miles (5 km) of Mount Greylock State Reservation Visitor Center and Jiminy Peak Mountain Resort. Crane Museum of Papermaking and Mountain Coaster are also within 6 miles (10 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We love staying at the school house. The location is ideal for our travels (Pittsfield, Stockbridge, Northampton, Bennington). Everything was neat and tidy and the kitchen area is perfect for cooking small meals. We were warm and comfortable even though it was chilly outside.
Our second stay at the school. It is absolutely perfect, near to everything and has every amenity needed (even for the miniature ponies across the street)
Such a cute old schoolhouse full of antiques. I loved staying in such a historical building. Host had great communication and lots of helpful tips. Thanks for sharing with us.
The property was very comfortable, nicely decorated, with good amenities. Downstairs is an historic school room from the 1800s; upstairs is the main living space.It's in a nice area, convenient to Mt. Greylock, close to lots of attractions.The owners were easy to reach and very nice.We highly recommend this property.
We spent three nights in the Stone Schoolhouse, hiking, visiting The Clarke, and enjoying a lovely evening concert at Tanglewood. Convenient location for seeing the Berkshires, unique quarters and friendly hosts. Highly recommend!
Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -
Amazing historical property in the heart of the Berkshire countryside with tons of charm and beauty. Helpful and accommodating hosts. Will definitely return!
What a fantastic place! Felt as if we were transported back in time. So much care and love has been put into making the Stone School Cottage welcoming and warm, and it shows throughout. A perfect staging spot for Berkshire adventures with my family, and a temporary home we anticipated returning to at the end of each day. Great hosts who are ready to assist with anything you might need, and they make it all so easy (check in, check out, questions). Am looking forward to my next visit!
Super comfortable and well-appointed apartment in a gorgeous neighborhood! This was the perfect place for a long stay, with a safe lobby and a trustworthy elevator. This area of Condesa is quiet and peaceful with a gorgeous path of trees and plants. There are many nice restaurants and a beautiful park. I highly recommend this apartment with its many amenities and great views!
It was a very quiet unique place to stay! You get a beautiful place with a lot of history and Good feel! I sent a picture to my dad and he Remembered using those same desks when he was a kid. Very nice weekend.
B K.
Stayed 2 nights in Jan 2025
Response from VrboOwner on 20 January 2025
Excellent, easy guests!
Archival
10/10 Excellent
Leanne J.
22 January 2014
Lovely Stay!
This is a very relaxing and charming place. The locations great and beautiful. I would recommend the school house to anyone who wants a pleasant stay. We will be back next year! Thanks for a great time !
Leanne J.
Response from VrboOwner on 17 March 2020
Thank you for your review - we really appreciate it. So glad that you enjoyed your long weekend and look forward to seeing you again!
Our family of 4 had a wonderful stay at this old schoolhouse. The attention to detail was impressive, right down to freshly cut flowers throughout. We loved that the history of the schoolhouse was on display, along with interesting relics from the 1800s/early 1900s. Everything was great and we hope to return one day!
First time staying in a school house! The upstairs living quarters are akin to a large studio apartment--nicely appointed and well laid out. The hosts, Cheryl and Rich are very welcoming too!
Love the warm feeling and history! Beautiful area with fun furry friends to visit down the road! We loved our much needed getaway from daily life to reconnect ❤️
Gregg and Suzanne F.
Stayed 1 night in Nov 2019
About the host
Hosted by Rich Cohen and Cheryl Sacks
Rich and Cheryl have been hosting guests at the Stone School Cottage for more than two decades.
Premier Host
They consistently provide great experiences for their guests