A lake surrounded by autumn-colored trees and a rocky shoreline.

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Pittsfield bed & breakfast

A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

1. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (426 reviews)
"A+ stay, everything was great about our stay here"
United States
Melissa
$140 nightly
The price is $154
Oct 25 - Oct 26
Total with taxes and fees
Snowed Inn
A two-story house with a porch, surrounded by trees.

2. Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.8 out of 10, Exceptional, (27 reviews)
"Cozy inn with great innkeepers and outstanding breakfast. Loved our room and our conversations with the innkeepers."
United States
John
$175 nightly
The price is $193
Nov 2 - Nov 3
Total with taxes and fees
Inn at Neshobe River
A large, two-story house with a central courtyard, surrounded by a well-maintained lawn and trees.

3. The Lilac Inn

The Lilac Inn
3.5 star property
Brandon
9.6 out of 10, Exceptional, (224 reviews)
"Great breakfast….friendly staff…spotless room"
United States
Judith M
$213 nightly
The price is $234
Nov 17 - Nov 18
Total with taxes and fees
The Lilac Inn
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

4. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (9 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
$222 nightly
The price is $245
Nov 1 - Nov 2
Total with taxes and fees
Deer Brook Inn
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

5. Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
$127 nightly
The price is $140
Nov 10 - Nov 11
Total with taxes and fees
Sleep Woodstock Mobility Impaired Accessible Suite
A row of cabins with a snow-covered ground and trees in the background.

6. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Our stay at this property was a pleasant surprise. Room was spotless and provided everything we needed. Bed was super comfortable and the location was perfect. There is a bit of road noise during the day but none at all at night. Would highly recommend this property."
United States
Mark & Joan S.
$152 nightly
The price is $167
Oct 28 - Oct 29
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

7. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
8.0 out of 10, Very good, (1 review)
"Old but nice and clean."
United States
James
$146 nightly
The price is $162
Oct 28 - Oct 29
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

8. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Considering the place was hit by a TORNADO the week prior to our visit, the accommodations were great, and the owner/host was in remarkably good spirits despite hassles with insurance."
United States
David M.
$159 nightly
The price is $175
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

9. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$159 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

10. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
8.0 out of 10, Very good, (1 review)
$152 nightly
The price is $167
Oct 28 - Oct 29
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

11. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$147 nightly
The price is $163
Nov 4 - Nov 5
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

12. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$159 nightly
The price is $175
Nov 16 - Nov 17
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

13. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$159 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

14. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$152 nightly
The price is $167
Oct 28 - Oct 29
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

15. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$134 nightly
The price is $148
Oct 28 - Oct 29
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

16. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$137 nightly
The price is $151
Nov 3 - Nov 4
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A house with a red roof, a porch with white railings, and a blue door.

17. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (71 reviews)
"We loved our stay here. Everyone was so nice. The beds were incredibly comfortable. We arrived in the late afternoon in time for happy hour. We sat outside near the fire pit and watched the sunset behind the mountains. It’s a little outside of Woodstock but very convenient."
United States
Michelle
$550 nightly
The price is $605
Oct 23 - Oct 24
Total with taxes and fees
Woodbridge Inn
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

18. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (332 reviews)
"Amazing stay and great restaurant!"
United States
Ava
$176 nightly
The price is $194
Nov 16 - Nov 17
Total with taxes and fees
The Jackson
A living room with a grey sectional sofa, a potted plant, and a radiator.

19. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (82 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
$165 nightly
The price is $182
Nov 9 - Nov 10
Total with taxes and fees
The Vesper
A modern fitness center with exercise equipment, mirrors, and a reception area.

20. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (54 reviews)
"My husband kept saying that the room was a model for providing everything a traveler might need. Lovely stay."
United States
Jeanne
$299 nightly
The price is $329
Oct 29 - Oct 30
Total with taxes and fees
Stay At Jimmy's
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

Emrose Luxury Cabins

Emrose Luxury Cabins

10/10 Excellent
"Absolutely beautiful stay and perfect for a comfortable get away for families/couples with respectable house rules. My family and I will make it a tradition to visit each year! Such an amazing property, accommodating staff, and amazing restaurants nearby!"
Katie Ann 2-night trip
Posted less than an hour ago
Emrose Luxury Cabins

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
933
Accommodation
33 B&B
Lowest Price
$140
Highest Price
$605

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 $140 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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