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Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
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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 5 - Nov 6
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, (240)
"Great stay! "
United States
Romulo
$175 nightly
The price is $193
Nov 5 - Nov 6
Total with taxes and fees
The Jackson
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 5 - Nov 6
Total with taxes and fees
Stay At Jimmy's
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
$161 nightly
The price is $178
Nov 12 - Nov 13
Total with taxes and fees
The Vesper
Iron/ironing board, travel crib, WiFi, bed sheets
Sleep Woodstock - 2 Double Beds - Dog Friendly
Sleep Woodstock - 2 Double Beds - Dog Friendly
10.0 out of 10, Exceptional, (2)
"The property is exactly as represented. It’s super clean. Comfortable beds. Bathrooms are updated and nice. It’s right across from a beautiful river and close proximity to quaint downtown Woodstock or nearby Killington. Felt safe and homey. Great communication from property owner. Would recommend! "
United States
stacey a.
$170 nightly
The price is $188
Nov 4 - Nov 5
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
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 5 - Nov 6
Total with taxes and fees
The Vermont 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
$215 nightly
The price is $237
Nov 12 - Nov 13
Total with taxes and fees
The Lilac 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
Outdoor pool
Echo Lake Inn
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, (98)
"Beautiful location and amazing staff and service"
United States
Lisa
$271 nightly
The price is $296
Nov 25 - Nov 26
Total with taxes and fees
Echo Lake Inn
Iron/ironing board, travel crib, WiFi, bed sheets
Sleep Woodstock - Dog Friendly King Suite
Sleep Woodstock - Dog Friendly King Suite
10.0 out of 10, Exceptional, (1)
"We had an excellent stay, everything was so clean, the room was well appointed and there was even a little communal area with laundry, kitchen, snacks, and shuffleboard. We would absolutely recommend this motel, it’s a gem! "
United States
Julie R.
$178 nightly
The price is $196
Nov 4 - Nov 5
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Iron/ironing board, travel crib, WiFi, bed sheets
Sleep Woodstock Mobility Impaired Accessible Suite
Sleep Woodstock Mobility Impaired Accessible Suite
$165 nightly
The price is $181
Nov 4 - Nov 5
Total with taxes and fees
Sleep Woodstock Mobility Impaired Accessible Suite
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

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"Quiet and low key. "
Corey 1-night trip
Posted 1 day ago
Comfort Inn Rutland - Killington

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
1,572
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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