Search B&B in Pittsfield

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
31 Muh. - 2 Saf.
In two weeks
7 Saf. - 9 Saf.
In one month
21 Saf. - 23 Saf.
In two months
21 Rab. I - 23 Rab. I

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, (319)
"Fantastic hosts, awesome breakfast, close to the mountain, cookies at night, hot tub, large fireplace best choice around "
The price is SAR 904
SAR 1,094 total
includes taxes & fees
29 Jan - 30 Jan
Snowed Inn
The Vesper
Room

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (13)
"I loved that this property was within walking distance to all the shops and restaurants in downtown Woodstock "
The price is SAR 475
SAR 522 total
includes taxes & fees
28 Jan - 29 Jan
The Vesper
The Jackson
Exterior

The Jackson

4.0 star property
10.0 out of 10, Exceptional, (193)
"the manager Lea was wonderful and most accommodating . she went above and beyond to be sure we had everything we needed. The inn is very quaint and exceptionally clean. The breakfast could use more choices if it is going to stay continental. Not what you would expect from a Bed and Breakfast! That would be our biggest complaint."
The price is SAR 791
SAR 870 total
includes taxes & fees
26 Jan - 27 Jan
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 Buckmaster Inn
Property entrance

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (59)
"Very charming B&B with amazing hosts!"
The Buckmaster Inn
The Vermont Inn
Front of property

The Vermont Inn

3.0 star property
9.2 out of 10, Wonderful, (392)
"This is the sweetest little inn with adorable rooms and common spaces. I loved that our room had a jacuzzi in the room. "
The Vermont Inn
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (182)
"Great place to Stay 5 STARS"
The price is SAR 842
SAR 926 total
includes taxes & fees
26 Jan - 27 Jan
The Lilac Inn
Mountain Valley Retreat
Property grounds

Mountain Valley Retreat

2.5 star property
9.8 out of 10, Exceptional, (157)
"Quiet charming home a few miles off the highway. Only 2 rooms and a very picturesque, relaxing setting. Will serve a home cooked full breakfast in the morning. "
The price is SAR 413
SAR 466 total
includes taxes & fees
26 Jan - 27 Jan
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
28 Jan - 29 Jan
Echo Lake Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (25)
"Stay at Jimmys is exceptional! From the second you pull into the lot you are greeted with pure joy. Jimmy came out and introduced himself welcoming us to his beautiful Inn. I travel around the globe and have never been welcomed this beautifully in all my life. The property is clean, peaceful, fabulously decorated. It’s so comfortable and welcoming. We didn’t want to leave! And guess what? Jimmy told us we could stay as long as we wanted the day of check out beaches they...
The price is SAR 934
SAR 1,027 total
includes taxes & fees
29 Jan - 30 Jan
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, (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.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (114)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 12+
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, (226)
"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...
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
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 spa 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 Lilac Inn: 9 rooms. 13.6 mi (21.9 km) from the heart of downtown. Enjoy the free cooked breakfast and unique décor. Mountain Valley Retreat: 2 rooms. Located 6.3 mi (10.1 km) from the core of Pittsfield. Enjoy the free full breakfast and private yard.
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.