Entire home

A Charming Mid 1800's Stockbridge Farmhouse.

Lakefront holiday home with kitchen and patio

Overview
Amenities
Policies
Location

Exceptional

4 bedrooms2 bathroomsSleeps 6

Popular amenities

Dryer
Parking available
Washer
Kitchen
Barbecue grill
Outdoor space

Explore the area

Stockbridge, MA

Place, Norman Rockwell Museum
‪4 min drive‬
Place, Naumkeag Museum
‪4 min drive‬
Place, National Shrine of the Divine Mercy
‪5 min drive‬
Airport, 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.

Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen

Washing machine

Dryer

Free WiFi

Air conditioning

Outdoor space

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Kitchen
Washer
Dryer
Free WiFi

House Rules

Check in after 4:00 PM

Check out before 11:00 AM

Children

Adults only

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

No cats

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.

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. The area's natural beauty can be seen at Monument Mountain and Fairfield Brook WMA, while Tanglewood Music Center and Mission House are cultural highlights. Berkshire Botanical Garden and Hoffman's Pottery are also worth visiting. Discover the area's water adventures with nearby swimming, or enjoy the great outdoors with hiking.

View more Holiday homes in Glendale

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
‪The Red Lion Inn - ‬3 min drive
‪Stockbridge Coffee And Tea - ‬4 min drive
‪Berkshire Mountain Bakery - ‬8 min drive
‪Six Depot Roastery and Cafe - ‬9 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).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Suzanne N.

18 Oct 2025

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

Lovely place! Super convenient & and comfortable!

Stayed 2 nights in Sep 2025

10/10 Excellent

Jamie H.

16 Jul 2025

It was a lovely c

Stayed 2 nights in Jun 2025

10/10 Excellent

Michael F.

6 Aug 2025

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

Cheryl P.

23 Sept 2025

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

Extremely clean house!! Mattresses are firm, but excellent quality. (Tissues in every room - a rarity for VRBO’s.) The house is your quintessential New England farmhouse, so stairs to bedrooms are narrow-ish and steep. Lovely county setting. Overall, a very nice experience.

Stayed 4 nights in Sep 2025

10/10 Excellent

Dianne F.

28 Dec 2024

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

Gary L.

8 Jun 2025

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

House

Excellent house and excellent communication!!

Stayed 3 nights in May 2025

10/10 Excellent

Liz B.

11 Sept 2024

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

Linda A.

30 Oct 2023

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

Rebecca L J.

8 Jul 2024

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

Sharon N.

5 Sept 2022

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.

29 Jun 2022

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.

30 Aug 2021

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.

22 Aug 2021

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.

16 Aug 2021

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.

9 Aug 2021

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

19 Jul 2021

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

13 Jun 2021

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.

19 Jul 2020

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.

23 Dec 2019

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.

18 Oct 2019

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

1 Sept 2019

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.

12 Aug 2019

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.

22 Jul 2019

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.

16 Dec 2018

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.

22 Aug 2018

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

About the host

Hosted by Mike Farley

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A Charming Mid 1800's Stockbridge Farmhouse.

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

Reviews

Popular amenities

Explore the area

Rooms & beds

4 bedrooms (sleeps 6)

Bedroom 1

Bedroom 2

Bedroom 3

Bedroom 4

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

About this property

A Charming Mid 1800's Stockbridge Farmhouse.

Add dates for prices

Amenities

Have a question?

Similar properties

Renovated Colonial on the River! Fantastic Views

House Rules

Children

Events

Pets

Smoking

Important information

You need to know

We should mention

About the area

Glendale

What's nearby

Getting around

Restaurants

Frequently asked questions

Reviews

Exceptional

10/10

10/10

10/10

10/10

10/10

Reviews

10/10 Excellent

Suzanne N.

Suzanne N.

10/10 Excellent

Jamie H.

Jamie H.

10/10 Excellent

Michael F.

Michael F.

10/10 Excellent

Cheryl P.

Cheryl P.

10/10 Excellent

Dianne F.

Christmas get away

Dianne F.

10/10 Excellent

Gary L.

House

Gary L.

10/10 Excellent

Liz B.

Lovely farmhouse in Stockbridge

Liz B.

10/10 Excellent

Linda A.

Old school beauty!

Linda A.

10/10 Excellent

Rebecca L J.

Stockbridge

Rebecca L J.

10/10 Excellent

Sharon N.

Berkshires getaway

Sharon N.