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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct

B&B in Pittsfield

The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (226)
"Great stay! "
The price is SAR 838
SAR 921 total
includes taxes & fees
7 Sep - 8 Sep
The Jackson
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (358)
"Beautiful place to stay! 10/10 would recommend. You're going to love it!"
The price is SAR 579
SAR 700 total
includes taxes & fees
26 Aug - 27 Aug
Snowed Inn
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (199)
"I love staying at the Lilac Inn when visiting family in the area. "
The price is SAR 834
SAR 917 total
includes taxes & fees
15 Sep - 16 Sep
The Lilac Inn
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (182)
"Great experience. Very accommodating! Room was great! Everything was clean and homemade breakfast was amazing. Thanks "
The price is SAR 413
SAR 466 total
includes taxes & fees
25 Aug - 26 Aug
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, (28)
"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"
The price is SAR 626
SAR 689 total
includes taxes & fees
24 Aug - 25 Aug
The Vesper
The Vermont Inn
Front of property

The Vermont Inn

3.0 star property
9.2 out of 10, Wonderful, (407)
"Great location & affordable lodging. "
The Vermont Inn
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Owners are warm and welcoming. Home is charming and well decorated, breakfast excellent. "
The Buckmaster Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (39)
"Superb stay in all ways!"
The price is SAR 747
SAR 822 total
includes taxes & fees
28 Aug - 29 Aug
Stay At Jimmy's
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
The price is SAR 1,655
SAR 1,821 total
includes taxes & fees
20 Sep - 21 Sep
Woodbridge Inn
Inn at Neshobe River
Exterior

Inn at Neshobe River

3.0 star property
9.4 out of 10, Exceptional, (13)
"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 "
The price is SAR 597
SAR 656 total
includes taxes & fees
25 Aug - 26 Aug
Inn at Neshobe River
Echo Lake Inn
Outdoor pool

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 SAR 839
SAR 915 total
includes taxes & fees
25 Aug - 26 Aug
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
Korean Gourmet Stay at Swiss Farm Inn - 1 night
Exterior

Korean Gourmet Stay at Swiss Farm Inn - 1 night

The price is SAR 1,501
SAR 2,400 total
includes taxes & fees
22 Aug - 23 Aug
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
Inn at Water's Edge
Bar (on property)

Inn at Water's Edge

3.0 star property
Inn at Water's Edge
Private 6-Room Vermont Inn for Groups – Daily Breakfast & Local Beers and Wines
Desk, iron/ironing board, free WiFi, bed sheets

Private 6-Room Vermont Inn for Groups – Daily Breakfast & Local Beers and Wines

Private 6-Room Vermont Inn for Groups – Daily Breakfast & Local Beers and Wines
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
"The hotel is very nice, very friendly, beautiful views specially from the room with balcony. Game room is awesome and the breakfast was delicious. Will come back again. "
DANIEL 2-night trip
Posted 1 day 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. 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. Snowed Inn: 19 rooms. Situated 8.9 mi (14.4 km) from the heart of Pittsfield. Enjoy the hot tubs and unique décor. The Vesper: 9 rooms. 18 mi (29 km) from the heart of downtown.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.