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The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Property class: 4.5

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Photo gallery for The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

A two-story house with a brick entrance and a white facade. - The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood (Stockbridge)
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building. - The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood (Stockbridge)
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden. - The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood (Stockbridge)
A neatly arranged bedroom with a bed, bedside table, and a dresser. - The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood (Stockbridge)
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains. - The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood (Stockbridge)
Located close to Norman Rockwell Museum and Berkshire Botanical Garden, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood provides free full breakfast, an adjacent golf course, and a terrace. Active travelers can enjoy fishing, horseback riding, and mountain biking at this bed & breakfast. Enjoy onsite activities like rowing/canoeing and kayaking. Free in-room WiFi is available to all guests, along with an art gallery on site and a garden.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services

Off-peak, on budget: 30% or more off select hotels in our fall sale

Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

Room options

View all photos for Suite, Private Bathroom (Parlour Suite)

A traditional bedroom with a four-poster bed, a fireplace, and floral wallpaper.

Suite, Private Bathroom (Parlour Suite)

  • Garden view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Suite, Private Bathroom (White Iron Suite)

A bedroom with a bed, a chair, a bedside table with a lamp, and floral wallpaper.

Suite, Private Bathroom (White Iron Suite)

  • Resort view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Suite, Private Bathroom (Ruffles Suite)

A bedroom with a canopy bed, floral wallpaper, a wooden dresser, and a chair.

Suite, Private Bathroom (Ruffles Suite)

8.0 out of 10
Very good
(1 review)
  • Resort view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Suite, Private Bathroom (Nells Suite)

A bedroom with floral wallpaper, a bedside table with a lamp, a bed with a pink blanket, and a chair with a floral cushion.

Suite, Private Bathroom (Nells Suite)

10.0 out of 10
Exceptional
(1 review)
  • Sleeps 2
  • 1 Queen Bed

View all photos for Suite, Private Bathroom (Stockbridge Suite)

A traditional bedroom with a bed, two chairs, a nightstand, and a dresser.

Suite, Private Bathroom (Stockbridge Suite)

10.0 out of 10
Exceptional
(1 review)
  • Sleeps 2
  • 1 King Bed

View all photos for Suite, Private Bathroom (Bens Suite)

A breakfast setup with tea cups, a teapot, a croissant, and a newspaper on a tray.

Suite, Private Bathroom (Bens Suite)

10.0 out of 10
Exceptional
(1 review)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Suite, Private Bathroom (RedBird Suite)

A traditional bedroom with a four-poster bed, a wooden dresser, a vanity with a mirror, and a red armchair.

Suite, Private Bathroom (RedBird Suite)

10.0 out of 10
Exceptional
(1 review)
  • Hill view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Suite, Private Bathroom (Maids Suite)

A hotel room with a large bed, a chair, a desk, and a window with curtains.

Suite, Private Bathroom (Maids Suite)

9.6 out of 10
Exceptional
(4 reviews)
  • Sleeps 2
  • 1 King Bed

About the neighborhood

Located in Stockbridge, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is next to a golf course and near a boardwalk/promenade. Norman Rockwell Museum and Tanglewood Music Center are cultural highlights, and some of the area's popular attractions include Berkshire Botanical Garden and Bousquet Ski Area. Naumkeag Museum and National Shrine of the Divine Mercy are two other places to visit that come recommended. Take an opportunity to explore the area for outdoor excitement like hiking/biking trails and other activities like skiing. Visit our Stockbridge travel guide
View more B&B in Stockbridge
Map
26 Glendale Road, RR 183, Stockbridge, MA, 01262

What's nearby

  • A wooden bridge over a river, surrounded by lush greenery and large rocks.
    Housatonic River
    2 min walk - 0.1 miles
  • A calm river surrounded by autumn foliage.
    Norman Rockwell Museum
    19 min walk - 1.0 mile
  • A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.
    Tanglewood Music Center
    13 min drive - 7.7 miles
  • Chesterwood
    15 min walk - 0.8 miles
  • National Shrine of the Divine Mercy
    6 min drive - 2.5 miles

Getting around

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

Restaurants

  • McDonald's
    14 min drive
  • McDonald's
    11 min drive
  • Berkshire Mountain Bakery
    5 min drive
  • Fresh City
    14 min drive
  • The Red Lion Inn
    3 min drive

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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free uncovered self parking on site
  • Wheelchair-accessible parking available

Food and drink

  • Free continental breakfast available daily 8:30 AM to 10:00 AM
  • Coffee and tea in common areas

Things to do

  • 18-hole adjacent golf course
  • Art gallery
  • Fishing
  • Hiking/biking trails
  • Horseback riding/rentals
  • Kayaking
  • Library
  • Mountain biking
  • Rowing/canoeing
  • Seasonal outdoor pool

Conveniences

  • Guidebooks
  • Laundry facilities
  • Limited-hour front desk

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Tour and ticket assistance
  • Turndown service
  • Wedding services

Business services

  • Computer station
  • Conference space
  • Meeting room

Outdoors

  • Barbecue grill
  • Garden
  • In a nature reserve
  • In the mountains
  • Picnic area
  • Pool loungers
  • Terrace

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 6 on-site accessible parking spaces
  • Upper floors accessible by stairs only
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking

More

  • 2 floors
  • Built in 1856
  • Colonial architecture
  • Fireplace in lobby
  • Smoking not allowed

Room amenities

Bedroom

  • Premium bedding

Bathroom

  • Bathrobes
  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Separate bathtub and shower
  • Towels provided

Entertainment

  • TV with cable channels

Food and drink

  • Chef service
  • Restaurant dining guides

More

  • Air conditioning
  • Ceiling fan
  • Individual decor
  • Individual furnishings
  • Iron/ironing board on request

Policies

Check-in

Check-in start time: 3 PM; Check-in end time: 7 PM

Minimum check-in age: 21

Check-out

Check-out before 11 AM

Special check-in instructions

The front desk is open daily from 8:30 AM - 6:00 PM

Front desk staffed during limited hours

If you are planning to arrive after 11:00 AM please contact the property in advance using the information on the booking confirmation

Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours), key retrieval

Pets

Pets not allowed

Children and extra beds

Children 17 and younger are not allowed at this property; All guests older than 17 are welcome

Rollaway/extra beds are not available

Cribs (infant beds) are not available

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Service fee: 8.3 percent

We have included all charges provided to us by the property.

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
Tax ID - C0000602830
This property accepts credit cards; cash is not accepted
Cashless transactions are available
Safety features at this property include a fire extinguisher, a smoke detector, a security system, and a first aid kit

We should mention

This property does not have elevators
The seasonal pool will be open from June to September
Pool access available from 9:00 AM to 6:00 PM
Children 17 years old and younger are not permitted at this property

Frequently asked questions

Does The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood have a pool?

Yes, this property has a seasonal outdoor pool. Pool access is from 9:00 AM–6:00 PM.

Is The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Self parking is free at this property.

What time is check-in at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood?

Check-in start time: 3 PM; Check-in end time: 7 PM.

What time is check-out at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood?

Check-out is at 11 AM.

Where is The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood located?

Situated in the mountains, this luxury bed & breakfast is 1 mi (1.6 km) from Norman Rockwell Museum and within 3 mi (5 km) of Berkshire Botanical Garden and Naumkeag Museum. National Shrine of the Divine Mercy and Tanglewood Music Center are also within 6 mi (10 km).

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Reviews

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood Reviews

9.2

Wonderful

9.4

Cleanliness

9.0

Location

9.4

Staff & service

9.0

Property conditions & facilities
Rating 10 - Excellent. 78 out of 118 reviews
Rating 8 - Good. 28 out of 118 reviews
Rating 6 - Okay. 9 out of 118 reviews
Rating 4 - Poor. 3 out of 118 reviews
Rating 2 - Terrible. 0 out of 118 reviews

Reviews

Verified review

10/10 Excellent

John

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very lovely beautiful Room and property The outside pool was not available
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Sarah

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a lovely stay and Diane and all the staff were really friendly and welcoming. The cooked to order breakfasts were delicious and filling. Can highly recommend.
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Carol Anne

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Linda

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Stockbridge Country Inn is the quintessential New England B&B! The owner, Diane, is the perfect host - very friendly and knowledgeable about the area. We stayed in The Maid's Suite which was extremely comfortable and beautifully decorated. Breakfast was always a delicious treat! The convenient location made access to sightseeing so easy.
Stayed 2 nights in Sep 2023
Verified review

6/10 Okay

Gina

Liked: Cleanliness, amenities, property conditions & facilities
It was extremely clean. Every crack and corner was spotless.
Verified review

10/10 Excellent

Roxanne

Liked: Cleanliness, amenities
My husband and I thoroughly enjoyed our stay at the Stockbridge Inn. Diane, the owner, greeted us warmly and escorted us to our room. Our accommodations were comfortable, warm and spacious and quiet enough for us to have a good night sleep. Diane was very helpful in recommending other accommodations for a large family function that she as unable to help us with. The breakfasts were incredible and the staff was there to answer our any desire. On a scale of 1-10 I would rate this Inn a ten.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Susan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is a charming old home. Rooms are fitted out for modern times. Breakfasts are outstanding and served in various charming dining spaces. Friendly and efficient and the chef did a fabulous job on the breakfasts. Tucked away but very close to the center of Stockbridge.
Stayed 2 nights in Aug 2023
Verified review

4/10 Poor

Kyungoh

Liked: Staff & service
Disliked: Property conditions & facilities
Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly.
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Patrick

Loved our stay. Breakfast was amazing.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Lynn P

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our stay at The Inn was wonderful. Diane and staff could not have been more welcoming or helpful with great suggestions. Shopping and picnic supplies were spot on! Breakfast was delicious and more than plentiful. The pool was not available at this time, but what a beautiful setting. We’ll stay here again on our next trip to the Berkshires.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Philippe

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood.
Stayed 5 nights in Jul 2026
Verified review

10/10 Excellent

Deborah

Liked: Staff & service, amenities, property conditions & facilities
Great breakfast, friendly helpful staff, pretty yard, good location
Stayed 3 nights in Aug 2022
Verified review

10/10 Excellent

Andrea

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating.
Stayed 2 nights in Oct 2023
Verified review

10/10 Excellent

Leon

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Our stay was perfect! The entire property was decorated in a heart fellt, beautiful way. Diane (We absolutely want to go back!the innkeeper) greeted us upon our arrival (which was later than anticipated), and was so accommodating My husband and I have been to several B&Bs, and this one was outstanding….
Stayed 2 nights in Oct 2022
Verified review

10/10 Excellent

GAEL

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved our stay at the Stockbridge Country Inn, it felt like being at home without doing your bed and breaksfast by yourself :-) Speaking of breakfast, it was quite a treat every morning to discover what they proposed and very difficult to choose between all the good options ! The area is also very peaceful and perfect to visit the Berkshires.
Stayed 3 nights in May 2022
Verified review

10/10 Excellent

Valerie

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Exceptional inn in Stockbridge MA

We stayed for 2 nights. Our wonderful owner greeted us warmly upon our arrival. Diane couldn’t be nicer. The house is beautifully kept and the room was very clean and and comfortable. The decor is very pretty and beautifully coordinated. The breakfast was excellent!!! The servers were lovely.
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

rene

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions
Stayed 1 night in Jul 2024
Verified review

10/10 Excellent

Julie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
What a treasure to be a guest in such a large and beautiful home. The room was like staying in a castle in England, with a huge bathroom. Double shower, clawfoot tub and gorgeous soft towels and sheets. The owners and staff were a joy to talk to and knew every inch of the area and people. The breakfasts were excellent. Candle lit, private table.
Stayed 2 nights in Oct 2021
Verified review

8/10 Good

Charnel Goff

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our room was small, and filled with beautiful antiques. The breakfasts were awesome, Diane, our innkeeper, is a wonderful cook and full of information about Stockbridge history and things to do in the area. Greeting us in the morning helping us with our plans for the day, snd asking us how the day went when we arrived back in the evening. It was special to meet her husband who is 99, and a World War II paratrooper.
Stayed 3 nights in Sep 2021
Verified review

10/10 Excellent

Verified traveler

Liked: Staff & service, amenities, property conditions & facilities
We can’t say enough good things about the Stockbridge country Inn. We loved our stay there. Far from the madding crowd but very centrally located. A little island Of calm. Delicious breakfasts and such gracious hosts. We loved our room. Comfy bed. The perfect getaway!
Stayed 3 nights in Jul 2021
Verified review

8/10 Good

John

Liked: Cleanliness, property conditions & facilities, room comfort

Foliage weekend, great location

Stay was nice at a beautiful time of year for the area. Inn did a thorough job with Covid precautions and cleanliness. Breakfast included with room was also good. Did have issue with Wifi in the room we were staying, which was a bit frustrating
Stayed 3 nights in Oct 2020
Verified review

10/10 Excellent

Joan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The house and grounds are lovely, well maintained and just a short drive away from Shakespeare and Co. Breakfast is delicious. A menu of items to choose from. The omelets are cooked to perfection! Diane is the perfect host. Very sweet and full of information and suggestions on what to do and where to shop for the everything from designer shoes and clothes in Lenox, to muffins and pies in Stockbridge and book stores in Great Barrington. I highly recommend a stay.
Stayed 2 nights in Jan 2020
Verified review

10/10 Excellent

Charles

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Diane is an absolutely lovely host--and breakfast at their table is a great experience.
Stayed 4 nights in Dec 2019