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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
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31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

B&B in Pittsfield

The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (234)
"Excellent Vintage style B&B. "
The Jackson
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (33)
"The location is fabulous bc you can walk everywhere once you arrive. Beds were comfortable and great options at breakfast(the oats and fresh strawberries were my favorite)"
The price is AED 730
AED 804 total
includes taxes & fees
30 Oct - 31 Oct
The Vesper
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (206)
"A quaint one night stay at Lilac House. Easy check in and check out. Room cozy. Enjoyed the ambiance of the B & B. Breakfast was delish. We would stay again! "
The price is AED 782
AED 860 total
includes taxes & fees
8 Oct - 9 Oct
The Lilac Inn
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (361)
"The inn truly stands out for it's naturally beautifully decorated all bright wooden interior. Their recent breakfast area expansion is wonderfully bright and cheery, as are the hosts. Thank you and we are looking forward to seeing you again!"
The price is AED 1,054
AED 1,276 total
includes taxes & fees
7 Oct - 8 Oct
Snowed Inn
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (63)
"Elizabeth and Richard are amazing people and welcomed us into their home. The property is beautifully maintained and Elizabeth's cooking is top notch. "
The Buckmaster Inn
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (183)
"Absolutely lovely stay!"
The price is AED 404
AED 457 total
includes taxes & fees
27 Oct - 28 Oct
Mountain Valley Retreat
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (42)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
The price is AED 1,098
AED 1,208 total
includes taxes & fees
26 Oct - 27 Oct
Stay At Jimmy's
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (66)
"Staff was very friendly and welcoming "
The price is AED 1,705
AED 1,876 total
includes taxes & fees
30 Sep - 1 Oct
Woodbridge Inn
The Vermont Inn
Front of property

The Vermont Inn

3.0 star property
9.2 out of 10, Wonderful, (408)
"Great location & affordable lodging. "
The price is AED 744
AED 811 total
includes taxes & fees
27 Oct - 28 Oct
The Vermont Inn
Chipman Inn
Exterior

Chipman Inn

Chipman Inn
Inn at Neshobe River
Exterior

Inn at Neshobe River

3.0 star property
9.4 out of 10, Exceptional, (15)
"Great little BAnd B just outside town. Shares property with a brewery and also offers a small food menu for dinner Fantastic view of the golf course 5 th hole Great hospitality and crazy good breakfast "
Inn at Neshobe River
Echo Lake Inn
Outdoor pool

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (97)
"Charming place, the food was great, rooms clean, and service was excellent"
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
Deer Brook Inn
Terrace/patio

Deer Brook Inn

4.0 star property
10.0 out of 10, Exceptional, (21)
"One of the best experiences I have ever had! The staff were kind, attentive, and just plain wonderful! I can't wait to return as soon as possible! This place is BEAUTIFUL inside and out! (Not to mention that the breakfast was to die for). Don't think twice- you need to stay at the Deer Brook Inn!"
Deer Brook Inn
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 Water's Edge
Bar (on property)

Inn at Water's Edge

3.0 star property
Inn at Water's Edge
All guest rooms in Chipman Inn- Your classic B&B in Vermont
Interior

All guest rooms in Chipman Inn- Your classic B&B in Vermont

All guest rooms in Chipman Inn- Your classic B&B in Vermont
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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Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Very easy check-in. Lovely staff, very friendly, and helpful. The only thing missing is a tea coffee maker in the room. Otherwise, everything else is excellent."
Patricia 1-night trip
Posted 5 days ago
The Mountain Inn at Killington

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. When you want to explore some attractions in town, Green Mountain National Forest and Roger Clark Memorial Central Library are worth a stop.
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. The Lilac Inn: 9 rooms. Situated 13.6 mi (21.9 km) from the heart of Pittsfield. Enjoy the free cooked breakfast and unique décor. Snowed Inn: 19 rooms. 8.9 mi (14.4 km) from the heart of downtown. Enjoy the hot tubs and unique décor. The Vermont Inn: 16 rooms. Located 9 mi (14.5 km) from the core of Pittsfield. Enjoy the 24-hour fitness center and sauna.
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.