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A Charming Mid 1800's Stockbridge Farmhouse.

Photo gallery for A Charming Mid 1800's Stockbridge Farmhouse.

Exterior
Terrace/patio
Exterior detail
Dining
Dining

Reviews

10 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Kitchen
  • Barbecue grill
  • Outdoor space

Explore the area

View map
Stockbridge, MA
  • Norman Rockwell Museum
    ‪4 min drive‬
  • Naumkeag Museum
    ‪4 min drive‬
  • National Shrine of the Divine Mercy
    ‪5 min drive‬
  • Hudson, NY (HCC-Columbia County)
    ‪49 min drive‬

Rooms & beds

4 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Bedroom 4

1 Double Bed

2 bathrooms

Bathroom 1

Bathtub or shower

Bathroom 2

Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Garden
Dining area

About this property

A Charming Mid 1800's Stockbridge Farmhouse.

Transform yourself in to the middle of a Norman Rockwell painting. It is easy to see how so many of his paintings were inspired by homes like these and the Stockbridge locals. Cherry Hill at Farley's Crossing has been owned by the same family for over 150 years.

A three minute drive from the famous Red Lion Inn in downtown Stockbridge brings you over Farley's Crossing and right up to 13 Cherry Street.

Whether you are in town to enjoy the Boston Symphony Orchestra at Tanglewood, or a day at the Stockbridge Bowl beach you have all the best activities near by.

Winter sports are all around you and Winter Holidays in Stockbridge are magical.

After a day of shopping and touring the famous Norman Rockwell museum, 13 Cherry Street awaits you with the peaceful serenity of the Berkshire mountains in your own backyard.
We can't wait to see you.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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Terrace/patio

Vacation in a Berkshire Farmhouse

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  • Free WiFi
  • Air conditioning
  • Parking available
9.8 out of 10, (96 reviews)
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House Rules

Check in after 4:00 PM
Check out before 11:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
No cats

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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Property Registration Number C0667213696

We should mention

A car is required for transport to and from this property

About the area

Glendale

Located in Glendale, this holiday home is in the city centre and on a lake. Tanglewood Music Center and Mission House are cultural highlights, and some of the area's attractions include Berkshire Botanical Garden and Hoffman's Pottery. Charles H. Baldwin & Sons and Hotchkiss Mobile Studio are also worth visiting. Swimming offers a great chance to get out on the surrounding water, or you can seek out an adventure with hiking nearby.
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Map
Stockbridge, MA

What's nearby

  • Norman Rockwell Museum - 4 min drive - 2.2 km
  • Naumkeag Museum - 4 min drive - 2.9 km
  • Berkshire Botanical Garden - 5 min drive - 4.6 km
  • National Shrine of the Divine Mercy - 5 min drive - 3.3 km
  • Tanglewood Music Center - 15 min drive - 13.5 km

Getting around

  • Pittsfield Intermodal Transportation Center - 25 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 23 min drive

Restaurants

  • ‪McDonald's - ‬16 min drive
  • ‪Pleasant and Main - ‬8 min drive
  • ‪The Red Lion Inn - ‬3 min drive
  • ‪Berkshire Mountain Bakery - ‬8 min drive
  • ‪Stockbridge Coffee And Tea - ‬4 min drive

Frequently asked questions

Is A Charming Mid 1800's Stockbridge Farmhouse. pet-friendly?

No, pets are not allowed at this property.

What time is check-in at A Charming Mid 1800's Stockbridge Farmhouse.?

Check-in begins at 4:00 PM.

What time is check-out at A Charming Mid 1800's Stockbridge Farmhouse.?

Checkout is at 11:00 AM.

Where is A Charming Mid 1800's Stockbridge Farmhouse. located?

Located in the heart of Glendale, this holiday home is within 1 mile (2 km) of Housatonic River and Mission House. Schantz Galleries and Berkshire Theatre Festival are also within 2 miles (3 km).

Reviews

10

Exceptional

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 32 out of 32 reviews
Rating 8 - Good. 0 out of 32 reviews
Rating 6 - Okay. 0 out of 32 reviews
Rating 4 - Poor. 0 out of 32 reviews
Rating 2 - Terrible. 0 out of 32 reviews

Reviews

10/10 Excellent

Jamie H.

It was a lovely c
Stayed 2 nights in Jun 2025

10/10 Excellent

Michael F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming old house from the 19th century within walking distance to downtown Stockbridge. Highly recommended
Stayed 7 nights in Jul 2025

10/10 Excellent

Gary L.

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

House

Excellent house and excellent communication!!
Stayed 3 nights in May 2025

10/10 Excellent

Dianne F.

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

Christmas get away

The house was beautiful. It was clean, on a quiet street and minutes from Main St. It was also only 10 to 15 minutes from other small towns in the area. We wouldn't hesitate to go back.
Stayed 4 nights in Dec 2024

10/10 Excellent

Rebecca L J.

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

Stockbridge

Very nice place for a large group. Well stocked kitchen. Immaculately clean. Nice quiet location, but you will need a car. All bedrooms are on the second floor and the stairs are steep and narrow, so not good for anyone with arthritic knees or ankles. Other than that, excellent stay.
Stayed 5 nights in Jul 2024

10/10 Excellent

Linda A.

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

Old school beauty!

This home was charming, warm and inviting. Bill the caretaker greeted us warmly and told us some of the family history. The home was immaculate and had all the immunities we needed. A definite A+.
Stayed 3 nights in Oct 2023

10/10 Excellent

Liz B.

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

Lovely farmhouse in Stockbridge

Lovely modernized farmhouse in a convenient Berkshires location. The kitchen is extremely well equipped for any kind of meal. Only complaint is size of beds. I believe some beds that I remember being listed as queens appeared to be doubles. The caretaker is located next door.
Stayed 10 nights in Aug 2024

10/10 Excellent

Sharon N.

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

Berkshires getaway

Beautifully maintained home in Stockbridge! Close to town, Tanglewood and Great Barrington. So charming and so clean! Would return again.
Stayed 3 nights in Sep 2022

10/10 Excellent

Jerry R.

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

A Week in the Berkshires

Lovely old home that has completely updated appliances and bathrooms. The house is immaculate and has everything you could possibly need. We loved our stay there and the caretaker that lives next door is wonderful and helpful for anything you need. We even saw a bear in the backyard! This is a very cozy home and we highly recommend it if you’re staying in this area.
Stayed 7 nights in Jun 2022

10/10 Excellent

Robert S.

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

Weekend in the Berkshires

Beautiful antique home. Spacious and well stocked.
Stayed 4 nights in Aug 2021

10/10 Excellent

Lesley S.

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

Berkshire Retreat

We stayed here for a family wedding and the house suited our multigenerational family perfectly. The wonderful set up of home enabled us to relax with plenty of porches. The house is very convenient to Stockbridge. We enjoyed the Norman Rockwell Museum as well as an Arts and Craft Fair during our stay. Perfect and the hosts were very friendly and helpful.
Stayed 3 nights in Aug 2021

10/10 Excellent

Sherry G.

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

Convenient location, clean, well-stocked, comfortable

See above
Stayed 5 nights in Aug 2021

10/10 Excellent

Alfred s.

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

Lovely stay

Clean house and well-stocked former farm house . As others have noted , like having the whole B&B to yourselves. On quiet street, a comfortable 1.3 mile walk to Stockbridge in one direction and the Norman Rockwell museum in the other.
Stayed 28 nights in Jul 2021

10/10 Excellent

susan s., Raleigh, NC

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

We loved the house and the area. We all had a wonderful time.

It was perfect for and what we wanted for Stockbridge.
Stayed 9 nights in Jul 2021

10/10 Excellent

Linda N., Worcester, MA

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

everything we hoped for

Great location, lovely grounds, friendly and helpful caretaker, clean and cozy and comfortable. Thanks!
Stayed 3 nights in Jun 2021

10/10 Excellent

Amy L.

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

Wonderful house, great visit

The house was just as pictured and described. Felt like staying in a B&B but it was all ours! Well appointed - plenty of kitchen items, great outdoor grill. Comfortable bedrooms, all air-conditioned. Bill, the caretaker, was friendly and attentive and happily helped us with myriad little details (lake passes, recycling, keeping the first floor cool, etc). We had a wonderful 2-week escape.
Stayed 16 nights in Jul 2020

10/10 Excellent

Cynthia K J.

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

Wonderful!

We had a great visit! The house was cozy and quaint! It had everything you could need and more!
Stayed 2 nights in Dec 2019

10/10 Excellent

Greg S.

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

Great Experience

Comfortable, clean, and well situated property. Bill the property manager was very friendly and helpful
Stayed 3 nights in Oct 2019

10/10 Excellent

Verified traveller

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

Beautiful Stockbridge

Lovely property, helpful owner, clean and well appointed. We very much enjoyed our month.
Stayed 30 nights in Aug 2019

10/10 Excellent

David D.

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

Very nice and close to Tanglewood

Everything was as expected
Stayed 7 nights in Jul 2019

10/10 Excellent

Michelle L.

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

Glorious Two Weeks in the Berkshires

This home is a gem - like stepping into a house painted by Norman Rockwell but with modern bathrooms and a well equipped kitchen. The house is convenient to all the sites you want to visit as well as the restaurants in Stockbridge, Lee and Great Barrington. Get an app like WAZE and drive the beautiful back roads to appreciate the charming countryside. Very comfy beds and the linens were top quality. The property manager was super responsive and the owners who live in the area went out of their way to make our stay perfect - fresh flowers, a pass to the Stockbridge "beach," outdoor recliners for sunning. One even used his local connections to get us a last minute reservation at an always packed, top of the line restaurant. The weather was delightful. Our only regret? Not booking the house for more time!
Stayed 13 nights in Jun 2019

10/10 Excellent

Dan M.

Perfect! Nice, comfy and VERY well kept!

What a beautiful, well kept and nice rental! This is an older home, with lots of character, but has been well maintained and upgraded to have all the modern conveniences, including nice new bathrooms, new kitchen with all modern appliances, and of course WiFi, essential these days. This has got to be one of the cleanest homes I have ever entered. Not a blemish or speck of dust anywhere. You hardly have to bring anything, the kitchen is fully equipped and there are plenty of nice towels, sheets, blankets, with all beds nicely made on arrival. The location is really hard to beat, quiet but just minutes drive to Stockbridge center, and from 5 to 15 minutes to Lenox, Stockbridge or Lee centers. Also, plenty of room for a family, everyone can have their own space when they want it. Dan M., Maplewood NJ
Stayed 4 nights in Nov 2018

10/10 Excellent

David S.

Great "Comfy" New England Home

We thoroughly enjoyed our 12 day stay at this wonderful family home near Stockbridge Center. The home was fully equipped with all necessary linens, towels, kitchenware and appliances, etc The motif is dated, but adds to the character of the home. The home comes with a family caretaker who lives in another structure on the grounds who is available to help in any way possible and who was very very attentive and friendly.
Stayed 11 nights in Jul 2018

10/10 Excellent

Elizabeth S.

Gratefull that we chose this home!

The home was clean, updated, and very comfortable. We will stay again and again in a home like this!
Stayed 2 nights in Apr 2018
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Meggan D.

charming comfortable house in beautiful area

Our family of 5, with 3 adult children, immensely enjoyed our Columbus Day weekend stay at the Stockbridge Farmhouse. The house feels very spacious - perks of eat in kitchen, separate dining room, ample sized bedrooms, lovely sitting and living room areas. It feels well loved and lived in, clean and well equipped. The cabinets in the kitchen go on and on - a space for everything, and every utensil, pot, pan you could want. Two sets of dishes, one for everyday and one in the china cabinet, for dinner parties. We had friends and family join us for dinner one night - there were eight of us at the table, and we didn't even use all the extra table leaves. But what I like most about the house is the feeling of peace that pervades it. The first floor living/dining/kitchen areas are at interesting angles to each other, so sitting in one, you can see through to another, each with its own windows looking in different directions. The house is surrounded by trees (there is a yard to sit in, don't worry). And the dappled sunlight in the morning is more than lovely. The house is in a great location: minutes away from Stockbridge town center (which is in the heart of the Berkshires) but with a feeling of being on its own, out in the country. Siblings Katie and Bill, whose great grandfather built this house, were super, very pleasant, efficient and helpful; Katie takes care of the arrangements, and Bill is the caretaker who lives in another house on the property. In short, I most highly recommend the Stockbridge Farmhouse for your stay in the Berkshires.
Stayed 3 nights in Oct 2016

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