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Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

Compare 15 B&B in Pittsfield with updated reviews, rates, and availability.

The Jackson
Exterior

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (212)
"The innkeeper, Lea, was excellent! She helped with our check in process. It went seamlessly. And she helped us when we had an issue with our TV. She was also extremely helpful with our breakfast and checkout! I would give her 5 stars! And the home was beautiful!!!"
The price is NT$7,258
NT$7,984 total
includes taxes & fees
Apr 27 - Apr 28
The Jackson
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (346)
"Fantastic and friendly "
The price is NT$5,562
NT$6,730 total
includes taxes & fees
May 22 - May 23
Snowed Inn
The Vesper
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.8 out of 10, Exceptional, (17)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is NT$3,658
NT$4,024 total
includes taxes & fees
Apr 29 - Apr 30
The Vesper
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (172)
"Place is away from hotels and restaurant strip. Very relaxing place, excellent breakfast. Will go back."
The price is NT$3,577
NT$4,042 total
includes taxes & fees
May 4 - May 5
Mountain Valley Retreat
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (186)
"This was a delightful stay and breakfast was wonderful. We will definitely return. "
The price is NT$7,446
NT$8,191 total
includes taxes & fees
May 1 - May 2
The Lilac Inn
The Vermont Inn
Seasonal outdoor pool, sun loungers

The Vermont Inn

3.0 star property
9.2 out of 10, Wonderful, (401)
"Awesome spot. "
The Vermont Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (29)
"Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return."
The price is NT$6,471
NT$7,118 total
includes taxes & fees
Apr 29 - Apr 30
Stay At Jimmy's
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Old fashioned inn with wonderful hosts."
The price is NT$7,497
NT$8,172 total
includes taxes & fees
May 26 - May 27
Echo Lake Inn
The Buckmaster Inn
Exterior

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
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
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
I.B. Munson House
Exterior detail

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 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
Inn at Water's Edge
Bar (on property)

Inn at Water's Edge

3.0 star property
Inn at Water's Edge
Deer Brook Inn
Property grounds

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
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

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, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.4 out of 10, (9)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is NT$7,056
NT$9,466 total
includes taxes & fees
Apr 29 - Apr 30
Mountain Green
Robert Frost Mountain Cabins
Cabin 1 (Pet Free) - Peak Perspective | Pillowtop beds, individually decorated, individually furnished

Robert Frost Mountain Cabins

3.5 star property
10.0 out of 10, Exceptional, (40)
"We loved how cozy and warm the cabin was, how easy the fireplace was to operate, and how much room we had. The view of sunrise from the back window and our ability to walk out there to enjoy it was a pleasant surprise. We'd love to come back."
The price is NT$8,750
NT$9,538 total
includes taxes & fees
May 2 - May 3
Robert Frost Mountain Cabins
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: 11 rooms. 17.2 mi (27.7 km) from the heart of Pittsfield. Enjoy the designer toiletries and library. The Vesper: 9 rooms. 18 mi (29 km) from the downtown core. Snowed Inn: 19 rooms. Situated 8.9 mi (14.4 km) from the heart of Pittsfield. Enjoy the hot tubs and unique décor. Mountain Valley Retreat: 2 rooms. 6.3 mi (10.1 km) from the heart of downtown. Enjoy the free full breakfast and private yard. Stay At Jimmy’s: 3 rooms. Located 18.2 mi (29.2 km) from the core of Pittsfield. Enjoy the jetted tubs 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 town, Green Mountain National Forest and Roger Clark Memorial Central Library are some notable sights to visit. You might check out Pittsfield Town Hall if you have time 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.