Entire home

Charming historic cottage on scenic road to Mt. Greylock

Cottage in Lanesborough with kitchen

Photo gallery for Charming historic cottage on scenic road to Mt. Greylock

Outdoor dining
Fridge, microwave, oven, stovetop
Exterior detail
2 bedrooms, desk, iron/ironing board, free WiFi
Property grounds
In the heart of the Berkshires, The Old Stone School offers a charming getaway amidst horse farms and scenic views. This historic building turned guest house features a private garden, alpacas and donkeys next door, and 5 acres of property where horses graze. Inside, enjoy antiques-filled rooms with broadband internet access.

Reviews

10 out of 10
Exceptional

Entire home

2 bedroomsSleeps 5149 sq m

Popular amenities

  • Kitchen
  • Air conditioning
  • Outdoor Space
  • Free WiFi
  • Mountain view

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

Property amenities

Ski

  • Close to skiing

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Car required
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Electric kettle
  • Kitchenette
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Books
  • DVD player
  • Games
  • Hulu
  • Netflix
  • Smart TV with cable/satellite channels
  • Streaming services
  • Video library

Outdoor areas

  • Garden

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • In a rural location
  • In a village
  • In the mountains

Things to do

  • Birdwatching nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Mountain biking nearby
  • Mountain climbing nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Housekeeping (on request)
  • Property located in a resort
  • Unit size: 1,600 square feet

Similar properties

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Check-out instructions

The host requires you 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.

Rules

We do not charge for children. Please indicate on

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number C0201341480

We should mention

A car is required for transportation to and from this property

Property is also known as

Charming Historic Cottage on Scenic Road to Mt. Greylock Cottage

About the neighborhood

Map
Lanesboro, MA

What's nearby

  • Mount Greylock State Reservation - 5 min drive - 2.2 km
  • Jiminy Peak Mountain Resort - 10 min drive - 11.1 km
  • Tanglewood Music Center - 29 min drive - 28.3 km
  • Ski Butternut - 50 min drive - 54.3 km
  • MVP Arena - 50 min drive - 65.3 km

Getting around

  • Pittsfield Intermodal Transportation Center - 12 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 21 min drive

Restaurants

  • ‪Old Man Jeff’s Barbecue Company - ‬11 min drive
  • ‪Dunkin' - ‬6 min drive
  • ‪Bob's Country Kitchen - ‬3 min drive
  • ‪Proprietor’s Lodge - ‬9 min drive
  • ‪Common Table - ‬12 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 is parking?

Onsite 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?

Check-out 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 mi (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 mi (10 km).

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Reviews

Charming historic cottage on scenic road to Mt. Greylock Reviews

10

Exceptional

10

Cleanliness

10

Location

6.0

Eco-friendliness

10

Property conditions & facilities
Rating 10 - Excellent. 110 out of 117 reviews
Rating 8 - Good. 6 out of 117 reviews
Rating 6 - Okay. 1 out of 117 reviews
Rating 4 - Poor. 0 out of 117 reviews
Rating 2 - Terrible. 0 out of 117 reviews

Reviews

10/10 Excellent

Isabel A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Comfortable, unique, great hosts, and a perfect location!
Stayed 2 nights in Aug 2025

10/10 Excellent

Marc S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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)
Stayed 4 nights in Aug 2025

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful property, wonderful owners

What a lovely property! And Rich was just terrific!
Stayed 3 nights in Jun 2025

10/10 Excellent

Amy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The schoolhouse was adorable. Very comfortable and clean. Decorated with so many interesting books and antiques.
Stayed 3 nights in Jul 2025

10/10 Excellent

Walter H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a great weekend stay. Hosts were great. Highly recommend. Building is unique and special.
Stayed 2 nights in Jun 2025

10/10 Excellent

Clay W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 5 nights in Jul 2025

10/10 Excellent

paula k.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute, historic cottage, close to Mt. Greylock

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.
Stayed 4 nights in Jun 2025

10/10 Excellent

Laurel K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quaint little cottage

We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!
Stayed 2 nights in Jan 2025

10/10 Excellent

Marc

Liked: Cleanliness, property conditions & facilities, communication
Fantastic stay. Hosts thought of everything. Very quiet and a charming space. Great access to the mountain, as well.
Stayed 4 nights in Aug 2024

10/10 Excellent

LF H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous Berkshire gem

Amazing historical property in the heart of the Berkshire countryside with tons of charm and beauty. Helpful and accommodating hosts. Will definitely return!
Stayed 2 nights in Feb 2025

10/10 Excellent

Mark S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Had a great timr
Stayed 3 nights in Jul 2023

10/10 Excellent

Kathleen R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved it!

A great unique place to stay!
Stayed 3 nights in Jun 2023

10/10 Excellent

Margaret B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location, fun cottage

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!
Stayed 3 nights in Aug 2024

10/10 Excellent

sara W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

We love the stone school - awesome location, great property and wonderful hosts! This is our second year coming and we'll be back next year!
Stayed 2 nights in Feb 2023

10/10 Excellent

Joseph H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very enjoyable stay

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 -
Stayed 7 nights in Sep 2024

10/10 Excellent

B K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Such a very nice place!

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.
Stayed 2 nights in Jan 2025

10/10 Excellent

Sara H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Historic Stay

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!
Stayed 2 nights in Aug 2024
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Leanne J., Hyannis, Mass.

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 !

10/10 Excellent

Richard M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

One of a Kind

Great host--genuinely friendly and genuinely helpful. Right at the base of Greylock. And just down the road from a miniature horse farm!
Stayed 2 nights in Aug 2024

10/10 Excellent

Irene H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely historic property

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!
Stayed 3 nights in Jul 2023

10/10 Excellent

Gregg and Suzanne F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

New chapters

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 ❤️
Stayed 1 night in Nov 2019

10/10 Excellent

Aub H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

One room schoolhouse

A great place in a great location with super-responsive and helpful owners! My partner is a teacher and she was entranced with the schoolroom, the history, and the old textbooks!
Stayed 2 nights in Jun 2024

10/10 Excellent

Mara K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend at Tanglewood

We were looking for a relaxing place for a weekend away, ending with a concert at Tanglewood...I came across the old school house, was immediately taken with it, and it did not disappoint. We thoroughly enjoyed our stay in this unique placec with close access to local hiking and biking options. Rich and Cheryl were gracious and flexible hosts.
Stayed 2 nights in Jul 2024

10/10 Excellent

Lea B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Magical lil retreat

I had a wonderful time. The lil stone house school is restored in a loving way! It feels homie and cosy and has a lot of stories to tell. The location is great for seeing museums or just go for a hike. Rich and Cheryl are on top with everything and very nice hosts!
Stayed 3 nights in Feb 2024

10/10 Excellent

Cort M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Unique and Lovely Place

This charming converted schoolhouse is well-supplied for the present day while reminding you of a bygone age. It's set among beautiful rural woods and pastures, private, but with ideal access to local attractions south, like Stockbridge and Lenox or north, like Williamstown and North Adams. The owners are extremely helpful and friendly, and they also simply allow you to enjoy your stay. A great place!
Stayed 3 nights in Jul 2023