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Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

B&B in Pittsfield

Exterior
Mountain Valley Retreat
Mountain Valley Retreat
2.5 star property
9.6 out of 10, Exceptional, (189)
"Absolutely lovely stay!"
United States
Elizabeth
$110 nightly
The price is $124
Nov 9 - Nov 10
Total with taxes and fees
Mountain Valley Retreat
Front of property
The Jackson
The Jackson
4.0 star property
9.8 out of 10, Exceptional, (241)
"Great stay! "
United States
Romulo
$175 nightly
The price is $193
Nov 10 - Nov 11
Total with taxes and fees
The Jackson
Exterior
Inn at Neshobe River
Inn at Neshobe River
3.0 star property
9.4 out of 10, Exceptional, (16)
"Beautiful upon arrival we were greeted by the host. She took plenty of time to show us around the property and explain how the bed-and-breakfast works and all the details of the winery brewery excellent day! Days of day."
United States
shawn
$189 nightly
The price is $208
Dec 5 - Dec 6
Total with taxes and fees
Inn at Neshobe River
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi
The Vesper
The Vesper
3.0 star property
9.0 out of 10, Wonderful, (41)
"The location is fabulous bc you can walk everywhere once you arrive. Beds were comfortable and great options at breakfast(the oats and fresh strawberries were my favorite)"
United States
Abigail
$160 nightly
The price is $177
Nov 13 - Nov 14
Total with taxes and fees
The Vesper
Front of property
Stay At Jimmy's
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, (46)
"Superb stay in all ways!"
United States
Scott
$199 nightly
The price is $219
Nov 10 - Nov 11
Total with taxes and fees
Stay At Jimmy's
Front of property
The Vermont Inn
The Vermont Inn
3.0 star property
9.2 out of 10, Wonderful, (412)
"Nice place. Rooms were nice and comfortable."
United States
Amy
$225 nightly
The price is $245
Nov 12 - Nov 13
Total with taxes and fees
The Vermont Inn
Front of property
Snowed Inn
Snowed Inn
3.5 star property
9.8 out of 10, Exceptional, (370)
"The inn truly stands out for it's naturally beautifully decorated all bright wooden interior. Their recent breakfast area expansion is wonderfully bright and cheery, as are the hosts. Thank you and we are looking forward to seeing you again!"
United States
Bradford
$265 nightly
The price is $292
Dec 3 - Dec 4
Total with taxes and fees
Snowed Inn
Exterior
The Lilac Inn
The Lilac Inn
3.5 star property
9.6 out of 10, Exceptional, (211)
"A quaint one night stay at Lilac House. Easy check in and check out. Room cozy. Enjoyed the ambiance of the B & B. Breakfast was delish. We would stay again! "
United States
Janet
$218 nightly
The price is $240
Nov 11 - Nov 12
Total with taxes and fees
The Lilac Inn
Outdoor pool
Echo Lake Inn
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, (98)
"The staff was super friendly, and welcoming "
United States
Janet
$271 nightly
The price is $296
Dec 8 - Dec 9
Total with taxes and fees
Echo Lake Inn
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

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!"
Desiree 1-night trip
Posted 2 days ago
Killington Mountain Lodge, Tapestry Collection by Hilton

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
1,585
Accommodation
17 B&B
Lowest Price
$124
Highest Price
$296

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Pittsfield?
Prices for B&Bs in Pittsfield often vary, but you can find a great deal from $124 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Pittsfield B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Pittsfield?
The most popular time to book a B&B in Pittsfield is during the vibrant summer months, particularly from July to September. This peak season attracts travelers eager to immerse themselves in the region's rich cultural offerings, including art festivals and outdoor concerts. The pleasant weather, with temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, creates an ideal backdrop for exploring the scenic beauty of the Berkshires.

In July, Pittsfield buzzes with activity, as visitors flock to enjoy local attractions such as the Berkshire Museum and the nearby Tanglewood Music Center. The warm days are superb for outdoor activities, including hiking and picnicking in the lush green parks that surround the area. Whether you're wandering through the charming downtown or taking in a live performance, the summer months offer a lively and engaging atmosphere.

For those looking for a more budget-friendly option, November presents a wonderful opportunity to experience the tranquil beauty of Pittsfield. While this month sees fewer tourists, it's the superb time to explore the stunning fall landscapes and enjoy the crisp air without the crowds. You can take leisurely strolls through the picturesque parks, visit local galleries, or indulge in cozy dining experiences at the area's charming restaurants.
What is the difference between a Pittsfield Bed and Breakfast and a hotel?
Every Pittsfield B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Pittsfield B&Bs.

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