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Compare 16 B&B in Pittsfield with updated reviews, rates, and availability.

Snowed Inn
Front of property
Snowed Inn
3.5 star property
9.8 out of 10, Exceptional, (309)
"The kindest and most accommodating hosts. We enjoyed their level of hospitality. The sleep was a bit interrupted throughout the night with doors constantly slamming. Overall though, we enjoyed our stay and will stay again (in a different room downstairs possibly). "
The price is AED 613
AED 742 total
includes taxes & fees
26 Nov - 27 Nov
Snowed Inn
The Jackson House Inn
Exterior
The Jackson House Inn
4.0 star property
10.0 out of 10, Exceptional, (180)
"Such a beautiful inn! Breakfast was amazing. "
The price is AED 729
AED 802 total
includes taxes & fees
24 Nov - 25 Nov
The Jackson House Inn
The Chipman Inn
Terrace/patio
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
Mountain Valley Retreat
Property grounds
Mountain Valley Retreat
2.5 star property
9.6 out of 10, Exceptional, (155)
"Nestled beneath Killington this cute gem was a lovely spot not too far off Rt4, for our overnight stay. Nicely clean, artfully decorated and equipped. Staff were lovely and breakfast was delicious."
The price is AED 404
AED 457 total
includes taxes & fees
24 Nov - 25 Nov
Mountain Valley Retreat
The Vesper
Room
The Vesper
3.0 star property
9.6 out of 10, Exceptional, (11)
"Dana and her staff were so welcoming and our experience was nothing less than perfect. My husband and I travel for a living and I feel like The Vesper is a little hidden gem that we have discovered and we look forward to staying there again. Stephanie Louris Ps.. Breakfast was so delicious!!"
The price is AED 565
AED 621 total
includes taxes & fees
25 Nov - 26 Nov
The Vesper
The Vermont Inn
Front of property
The Vermont Inn
3.0 star property
9.2 out of 10, Wonderful, (389)
"Nice place. Rooms were nice and comfortable."
The Vermont Inn
Stay At Jimmy's
Front of property
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, (21)
"Wow! Loved our visit at Stay at Jimmy's. Room was beautifully decorated and supplied with everything we needed. Location was perfect for exploring Woodstock. We had excellent communication from John and Jimmy. A bonus for us was the EV charging station across the street. "
The price is AED 915
AED 1,006 total
includes taxes & fees
24 Nov - 25 Nov
Stay At Jimmy's
The Lilac Inn
Exterior
The Lilac Inn
3.5 star property
9.6 out of 10, Exceptional, (177)
"The Lilac Inn was lovely and the Inn owner was welcoming. The 2 bed room my daughter and I shared was very nice and comfortable. The Inn was an easy walk to downtown."
The price is AED 788
AED 867 total
includes taxes & fees
3 Dec - 4 Dec
The Lilac Inn
The Buckmaster Inn
Property entrance
The Buckmaster Inn
3.0 star property
10.0 out of 10, Exceptional, (56)
"Elizabeth and Richard were absolutely wonderful hosts! I enjoyed every second of staying at this property. They went out of their way to be hospitable and to make all guests comfortable. The breakfast was fantastic each day and they had wonderful suggestions for the local area. I was already planning a trip back before I had even checked out. Highly recommend!!"
The Buckmaster Inn
Echo Lake Inn
Front of property
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is AED 910
AED 992 total
includes taxes & fees
11 Dec - 12 Dec
Echo Lake Inn
The Woodstocker B&B
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 Woodstocker B&B
Woodbridge Inn
Front of property - evening/night
Woodbridge Inn
3.0 star property
9.6 out of 10, Exceptional, (64)
"Darling -- Wonderful location, hosts and great breakfast -- We will be back during ski season. Thank you. "
Woodbridge Inn
Deer Brook Inn
Property entrance
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
Inn at Water's Edge
Front of property
Inn at Water's Edge
3.0 star property
Inn at Water's Edge
Inn at Neshobe River
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
I.B. Munson House
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
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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Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 12+
Here's the main living area - dining is up on the left
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (113)
"We stayed for a small bachelor party and had a great time! Everyone had room and there was plenty to do."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
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.

Frequently asked questions

Searching for B&Bs in Pittsfield?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a bed and breakfast may be the perfect thing for your getaway to Pittsfield. If your ideal vacation to Pittsfield includes spending lots of time outside, Green Mountain National Forest is a good spot to enjoy the scenery.
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 Jackson House Inn: 11 rooms. 17.2 mi (27.7 km) from the heart of Pittsfield. Enjoy the designer toiletries and library. Snowed Inn: 19 rooms. 8.9 mi (14.4 km) from the downtown core. Enjoy the spa tubs and unique décor. 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 Lilac Inn: 9 rooms. Located 13.6 mi (21.9 km) from the core of Pittsfield. Enjoy the free cooked breakfast and unique décor.
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 December, with each month seeing an average of 10 inches of snowfall.
What is there to do in Pittsfield?
When you want to explore some things to do in Pittsfield, consider a visit to Green Mountain National Forest. Appalachian Trail Adventures and Pico Mountain at Killington Ski Resort are also some sites to visit 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.