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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
Adams
8.8 out of 10, Excellent, (141)
"It was clean and quiet good Breakfast "
United States
William
The price is HK$1,310
HK$1,464 total
includes taxes & fees
13 Nov - 14 Nov
The Trail in Adams - Berkshires’ Art Hotel
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (52)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is HK$1,835
HK$1,940 total
includes taxes & fees
1 Dec - 2 Dec
Harbour House Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew which was appreciated. We look forward to coming back"
United States
Samuel
Chambery Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (287)
"Great Views & Hospitality"
United States
Gerald
The price is HK$1,338
HK$1,569 total
includes taxes & fees
13 Nov - 14 Nov
Lakehouse Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"A first class little inn"
United States
Philip
The price is HK$1,950
HK$2,287 total
includes taxes & fees
18 Nov - 19 Nov
The Inn at Stockbridge
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (434)
"Nice place, easy check in"
United States
Robert
The price is HK$789
HK$866 total
includes taxes & fees
13 Nov - 14 Nov
Shaker Mill Inn
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Lenox
The price is HK$1,625
HK$2,379 total
includes taxes & fees
13 Nov - 14 Nov
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had a wonderful stay. We are so glad we chose this inn. The location is superb…a five-minute walk to the center of Lenox! It is a beautiful inn with a lot of charm, and the staff is warm and friendly. We loved our large room too! Definitely plan on staying here again when we come back to the area! "
United States
Itzhak
The price is HK$1,316
HK$1,470 total
includes taxes & fees
13 Nov - 14 Nov
Whistler's Inn Bed & Breakfast
1 bedroom, premium bedding, iron/ironing board, free WiFi
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
United States
Amanda
The price is HK$1,702
HK$1,702 total
includes taxes & fees
11 Dec - 12 Dec
Tanglewood Suites
Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is HK$3,277
HK$3,661 total
includes taxes & fees
3 Dec - 4 Dec
33 Main
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Very friendly staff. "
United States
Pamela
The price is HK$971
HK$1,389 total
includes taxes & fees
13 Nov - 14 Nov
The Cornell Inn, Lenox & The Berkshires
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (87)
"I’m a former travel writer and hotel reviewer at the NY Times Sunday Travel and I’ve been coming to the Berkshires the past decade. This is the hands down the best B&B in the area. The decor, the ambiance, the artistic details, the warm customer service, the made-to-order gourmet breakfast next to a wood-burning fireplace - all make this place so cozy and truly unique. Listen to the jukebox or play billiards in the inn’s great room. Or lounge beneath the heat lamps on its wraparound porch. You...
United States
Lionel
The price is HK$1,741
HK$1,945 total
includes taxes & fees
21 Nov - 22 Nov
Granville House
Business centre
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"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!!!"
United States
Carol Anne
The price is HK$2,968
HK$3,591 total
includes taxes & fees
8 Dec - 9 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

Lenox
The price is HK$1,874
HK$2,701 total
includes taxes & fees
13 Nov - 14 Nov
Cozy Carriage House room with a double bed and private balcony
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
The price is HK$1,625
HK$2,379 total
includes taxes & fees
13 Nov - 14 Nov
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
The price is HK$1,998
HK$2,857 total
includes taxes & fees
13 Nov - 14 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.

Lenox
The price is HK$1,749
HK$2,536 total
includes taxes & fees
17 Nov - 18 Nov
Elegant Carriage House room with a queen bed and private patio.
Fireplace
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Lenox
The price is HK$2,558
HK$3,569 total
includes taxes & fees
16 Nov - 17 Nov
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Lenox
The price is HK$2,806
HK$3,890 total
includes taxes & fees
16 Nov - 17 Nov
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Excellent staff and room. "
Philip 2-night trip
Posted 3 days ago
Hotel On North

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
2,645
Accommodation
35 B&B
Lowest Price
HK$866
Highest Price
HK$3,890

Frequently asked questions

Searching for B&Bs in Pittsfield?
If you're hoping for something a little more offbeat than your standard hotel, a bed and breakfast could be a great option for your trip. If you want to lose yourself exploring fascinating exhibits, you might consider stopping by Berkshire Museum and Hancock Shaker Village while you're in town.
How do you know if a B&B is the best choice for your stay?
With attentive service, opportunities to interact with the owner and tasty breakfasts, B&Bs offer a one-of-a-kind environment.
What are the best B&Bs in Pittsfield?
Here are some well-liked B&Bs in the surrounding area: The Cornell Inn, Lenox & The Berkshires: 5.9 mi (9.4 km) from the heart of Pittsfield. Enjoy the free full breakfast and unique decor. Shaker Mill Inn: 9 rooms. 9.8 mi (15.8 km) from the city centre. Lakehouse Inn: 14 rooms. Situated 8.5 mi (13.6 km) from the heart of Pittsfield. Enjoy the free full breakfast and snack bar/deli. Whistler's Inn Bed & Breakfast: 14 rooms. 6.1 mi (9.8 km) from the city centre. Enjoy the private garden and unique decor. Chambery Inn: 9 rooms. Located 9.7 mi (15.5 km) from the core of Pittsfield. Enjoy the private garden and snack bar/deli.
When is the best time to stay at a B&B in Pittsfield?
When you're dreaming of a trip to Pittsfield, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Pittsfield?
When you want to explore some cultural attractions on your trip, Berkshire Museum and Colonial Theater are worthy sites to visit. You should put Barrington Stage Company and Bousquet Ski Area on your list if you want to see more of the area.
How can I get to and around Pittsfield?
You can plan your excursions in and around Pittsfield ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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