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Compare 17 B&B in Pittsfield with updated reviews, rates, and availability.

Exterior
The Lilac Inn
3.5 star property
9.4 out of 10, Exceptional, (157)
"Incredibly great service and great food. "
The price is $165
$182 total
includes taxes & fees
May 29 - May 30
The Lilac Inn
Fireplace
The Jackson House Inn
4.0 star property
10.0 out of 10, Exceptional, (167)
"Fantastic homemade breakfast and cookies at night. The rooms were very clean and comfortable. The staff was fantastic! Will be staying again. Book directly and save money."
The price is $263
$289 total
includes taxes & fees
May 26 - May 27
The Jackson House Inn
Exterior
Mountain Valley Retreat
2.5 star property
9.6 out of 10, Exceptional, (133)
"Mike is an excellent host with great attention to detail. Would highly recommend this spot for whatever occasion takes you to Killington area. "
The price is $110
$121 total
includes taxes & fees
May 28 - May 29
Mountain Valley Retreat
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View from property
The Chipman Inn
3.0 star property
9.6 out of 10, Exceptional, (138)
"This is a lovely old Inn. We found that there was not good lighting to read in our room and just one chair. As the weather was poor It would have been nice to spend time reading. Ther is a couch downstairs that we could have used. "
The Chipman Inn
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets
The Vesper
3.0 star property
8.0 out of 10, Very Good, (1)
" Goof"
The price is $137
$151 total
includes taxes & fees
May 27 - May 28
The Vesper
Front of property - evening/night
Woodbridge Inn
3.0 star property
9.6 out of 10, Exceptional, (57)
"Very nice experience. The people running the bed and breakfast were very nice "
Woodbridge Inn
Front of property
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, (1)
"Our short but sweet stay was great. Check in was smooth and the breakfast bundles were a nice touch. The rooms are newly designed and felt like such a getaway!"
The price is $224
$247 total
includes taxes & fees
Jun 2 - Jun 3
Stay At Jimmy's
Exterior
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, (90)
"Lovely inn. Went to VT to see the total eclipse "
The price is $191
$209 total
includes taxes & fees
Jun 11 - Jun 12
Echo Lake Inn
Exterior
The Buckmaster Inn
3.0 star property
10.0 out of 10, Exceptional, (49)
"This Inn was built in 1801, so it’s a very old Inn. There are not enough superlatives. Fantastic. Awesome. Amazing. Going back definitely. All rooms are beautifully furnished with four-posters and very comfortable chairs. Place to be lived in. Immaculately clean. As soon as you walk in you want to stay forever. Warm. Delicious homemade breakfasts. Innkeeper Elizabeth is friendly and accommodating. We could have talked for hours. Still blissing out days later. "
The Buckmaster Inn
Front of property
The Vermont Inn
3.0 star property
9.2 out of 10, Wonderful, (382)
"Very comfortable and clean. Conveniently located with much more charm and ambiance than chain hotels. Thoroughly enjoyed our stay!! Breakfast was great!! "
The Vermont Inn
Outdoor spa tub
Snowed Inn
3.5 star property
9.8 out of 10, Exceptional, (252)
"The place is beautiful and the iwners are super friendly. The breakfast was delicious. Great place!"
The price is $132
$159 total
includes taxes & fees
May 26 - May 27
Snowed Inn
Front of property
The Woodstocker B&B
4.0 star property
10.0 out of 10, Exceptional, (50)
"This is a lovely and charming guest house / B&B, run by a very nice and friendly couple. During our stay they recommended a number of places to visit and were warm and welcoming every day. I would not hesitate to book with them again."
The price is $284
$337 total
includes taxes & fees
May 26 - May 27
The Woodstocker B&B
Terrace/patio
Deer Brook Inn
4.0 star property
10.0 out of 10, Exceptional, (21)
"The Inn was so lovely and charming and exceeded our expectations! The hospitality offered by the Inn Keeper and his team was truly remarkable and we felt welcome and spoiled throughout our stay. The property itself is stunning and the attention to detail is five star in our book!!! We will definitely be back! Plan your stay!! You won’t be disappointed!!"
Deer Brook Inn
Bar (on property)
Inn at Water's Edge
4.0 star property
Inn at Water's Edge
Exterior
I.B. Munson House
3.0 star property
10.0 out of 10, Exceptional, (12)
"The hosts Gloria and Stephen were so friendly and sweet! The house is beyond gorgeous and incredibly cozy. The room itself was beautifully appointed and we had a claw foot bathtub (swoon)! Breakfast every morning was delicious. Would love to return someday!"
I.B. Munson House
Exterior
Inn at Neshobe River
3.0 star property
9.0 out of 10, Wonderful, (10)
"Owners were so nice, bed was great, linens and towels were wonderful. House is very old and only drawback (which is original to the house and should not be changed!) is the bar/latch style door handles. The Violet Room has its private bathroom across the hall landing, but if you get up in the night as we do, you do make a lot of noise rattling those handles! Walls are thin.But that didn't disturb us, since the other patrons on our visit were very quiet and considerate. If you are looking for...
Inn at Neshobe River
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See all available properties in Pittsfield
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.

Other property types in Pittsfield

Property grounds
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (108)
"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the time we left. Thank you David! We are looking forward to next year."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (194)
"Cabin was so wonderful, fire place was lovely right next to the hot tub. Host was great with communication. Very pleasant stay. Cozy, quiet, clean cabin."
Cozy Loft for two with Hot Tub
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (447)
"Clean and quiet cabin. Perfect for a getaway."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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.

Pittsfield B&B information

Number of reviews
1,481
Accommodation
17 B&B
Lowest Price
$110
Highest Price
$284

Frequently asked questions

Searching for B&Bs in Pittsfield?
If you’re looking for something a little more offbeat than your standard hotel experience, a stay at a bed and breakfast could be the perfect alternative for your getaway.
Why should you consider B&Bs instead of traditional hotels?
With attentive service, opportunities to meet other guests, and hearty breakfasts, B&Bs provide a unique environment.
What are the best bed and breakfasts in Pittsfield?
Here are some well-liked B&Bs in the area: The Lilac Inn: 9 rooms. 13.6 mi (21.9 km) from the heart of Pittsfield. Enjoy the free cooked breakfast and unique décor. Mountain Valley Retreat: 2 rooms. 6.3 mi (10.1 km) from the downtown core. Enjoy the free full breakfast and private yard. The Vesper: 9 rooms. Situated 18 mi (29 km) from the heart of Pittsfield. The Chipman Inn: 9 rooms. 17.9 mi (28.8 km) from the heart of downtown. Enjoy the free full breakfast and skiing access. The Jackson House Inn: 11 rooms. Located 17.2 mi (27.7 km) from the core of Pittsfield. Enjoy the free full breakfast and designer toiletries.
When should I book my B&B in Pittsfield?
When you’re dreaming of a escape to Pittsfield, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and April, with each month seeing an average of 10 inches of snowfall.
What is there to do in Pittsfield?
When you want to spend some time in the great outdoors, Lake Dunmore and Gifford Woods State Park are some notable spots. You might put Pico Mountain at Killington Ski Resort and Killington Resort on your list if you want to see more of the area.
How can I get to and around Pittsfield?
You can map out your trip in and around Pittsfield ahead of time with these transportation options. Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) from the heart of the city. Otherwise, you can search for flights to Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. If you’d like to explore around the area, you may want a rental car for your journey.

Recent reviews of Pittsfield hotels
Expedia verified reviews

North Star Lodge and Resort

North Star Lodge and Resort

5/5 Excellent
"Late season stay, great price and service. "
A verified traveler stayed at North Star Lodge and Resort
Posted 13 hours ago
North Star Lodge and Resort