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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

B&B in Pittsfield

The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (216)
"What a lovely place to stay. The couple that manage The Jackson are absolutely wonderful and made our stay fabulous. I would highly recommend staying here with gorgeous surroundings, charming rooms and lovely hospitality."
The Jackson
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (177)
"Beautiful scenery. Accommodating hosts, helpful to move my luggage up and down staircase, even putting into my car when I departed. Excellent made to order breakfast, multiple decaf coffee refills, even preparing a to go coffee in my travel cup. I would definitely stay again when visiting this region. A gem."
The price is AED 404
AED 456 total
includes taxes & fees
18 Jun - 19 Jun
Mountain Valley Retreat
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (20)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is AED 643
AED 707 total
includes taxes & fees
18 Jun - 19 Jun
The Vesper
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (350)
"Such a beautiful and cozy place to stay!! Welcoming atmosphere and people! Had a wonderful time!"
The price is AED 481
AED 582 total
includes taxes & fees
18 Jun - 19 Jun
Snowed Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (31)
"Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return."
The price is AED 731
AED 804 total
includes taxes & fees
17 Jun - 18 Jun
Stay At Jimmy's
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (189)
"Great place to Stay 5 STARS"
The price is AED 757
AED 833 total
includes taxes & fees
24 Jun - 25 Jun
The Lilac Inn
The Vermont Inn
Front of property

The Vermont Inn

3.0 star property
9.2 out of 10, Wonderful, (402)
"Great location & affordable lodging. "
The Vermont Inn
Inn at Neshobe River
Exterior

Inn at Neshobe River

3.0 star property
9.2 out of 10, Wonderful, (11)
"This is a charming BNB. Our room was gorgeous, the bed very comfortable and the breakfast delicious. The inn keepers are delightful and the definition of hospitable and welcoming. The Inns setting is lovely with well kept and lovely grounds. A real bonus is that right next door is a craft beer and wine tasting room. The award winning beer was great!"
The price is AED 547
AED 602 total
includes taxes & fees
22 Jun - 23 Jun
Inn at Neshobe River
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
Woodbridge Inn
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Very charming B&B with amazing hosts!"
The Buckmaster Inn
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Charming place, the food was great, rooms clean, and service was excellent"
The price is AED 736
AED 803 total
includes taxes & fees
18 Jun - 19 Jun
Echo Lake Inn
The Woodstocker B&B
Exterior

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
Korean Gourmet Stay at Swiss Farm Inn - 1 night
Exterior

Korean Gourmet Stay at Swiss Farm Inn - 1 night

The price is AED 1,469
AED 2,320 total
includes taxes & fees
17 Jun - 18 Jun
Korean Gourmet Stay at Swiss Farm Inn - 1 night
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
Deer Brook Inn
Terrace/patio

Deer Brook Inn

4.0 star property
10.0 out of 10, Exceptional, (21)
Deer Brook Inn
Inn at Water's Edge
Bar (on property)

Inn at Water's Edge

3.0 star property
Inn at Water's Edge
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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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 surrounding area: Korean Gourmet Stay at Swiss Farm Inn - 1 night: 0.5 mi (0.8 km) from the heart of Pittsfield.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. 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.