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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

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, (326)
"Cozy and-clean with welcoming hosts ."
The price is SAR 824
SAR 997 total
includes taxes & fees
16 Mar - 17 Mar
Snowed Inn
The Vesper
Room

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (14)
"I loved that this property was within walking distance to all the shops and restaurants in downtown Woodstock "
The price is SAR 486
SAR 535 total
includes taxes & fees
20 Feb - 21 Feb
The Vesper
The Jackson
Exterior

The Jackson

4.0 star property
10.0 out of 10, Exceptional, (200)
"Great stay clean and comfortable. Staff was very accommodating and friendly. "
The price is SAR 837
SAR 921 total
includes taxes & fees
2 Mar - 3 Mar
The Jackson
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
The Vermont Inn
Front of property

The Vermont Inn

3.0 star property
9.2 out of 10, Wonderful, (396)
"We had a really nice time there. "
The Vermont Inn
The Buckmaster Inn
Property entrance

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"I had a great stay at the Buckmaster Inn for ski weekend at Okemo. The house is beautiful with many classic colonial touches throughout. Best of all, Richard and Elizabeth are gracious hosts who go above and beyond to make their guests comfortable. It snowed the last night of my stay and Richard got up extra early to clear the driveway and my car! I will be back whenever I can visit. "
The Buckmaster Inn
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (183)
"Great place to Stay 5 STARS"
The price is SAR 859
SAR 945 total
includes taxes & fees
17 Feb - 18 Feb
The Lilac Inn
Mountain Valley Retreat
Property grounds

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (164)
"Wonderful place to stay! My son and I came up for a couple days of skiing, this was the perfect place to stay. The hosts are extremely kind, the room was very comfortable, and they made a delicious breakfast for us each morning. We will definitely stay here again when we come to Killington."
The price is SAR 413
SAR 466 total
includes taxes & fees
18 Feb - 19 Feb
Mountain Valley Retreat
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 SAR 951
SAR 1,037 total
includes taxes & fees
19 Mar - 20 Mar
Echo Lake Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (26)
"Good ownership, very helpful"
The price is SAR 934
SAR 1,027 total
includes taxes & fees
17 Feb - 18 Feb
Stay At Jimmy's
The Woodstocker B&B
Front of property

The Woodstocker B&B

4.0 star property
10.0 out of 10, Exceptional, (51)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
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
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
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
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

Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (230)
"Would definetly go back. Enjoyable, quiet, just an enjoyable stay!"
Cozy Loft for two with Hot Tub
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, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (43)
"Great location, great accommodations. Easy in and out, no issues at all!"
The price is SAR 356
SAR 678 total
includes taxes & fees
18 Feb - 19 Feb
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
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: Snowed Inn: 19 rooms. 8.9 mi (14.4 km) from the heart of Pittsfield. Enjoy the hot tubs and unique décor. The Jackson: 11 rooms. 17.2 mi (27.7 km) from the downtown core. Enjoy the designer toiletries and library. The Vesper: 9 rooms. Situated 18 mi (29 km) from the heart of Pittsfield. The Vermont Inn: 16 rooms. 9 mi (14.5 km) from the heart of downtown. Enjoy the 24-hour fitness center and sauna. The Chipman Inn: 9 rooms. Located 17.9 mi (28.8 km) from the core of Pittsfield. Enjoy the free full breakfast and skiing access.
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. Killington Resort and Appalachian Trail Adventures 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.