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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

B&B in Pittsfield

Exterior
Mountain Valley Retreat

Mountain Valley Retreat

2.5 star property
Killington
9.6 out of 10, Exceptional, (189)
"Absolutely lovely stay!"
United States
Elizabeth
The price is AED 404
AED 457 total
includes taxes & fees
16 Nov - 17 Nov
Mountain Valley Retreat
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (247)
"The room, the staff, the amenities were what we were hoping for. The Jackson is a great place to stay! "
United States
Frederick
The Jackson
Exterior
Inn at Neshobe River

Inn at Neshobe River

3.0 star property
Brandon
9.4 out of 10, Exceptional, (16)
"Beautiful upon arrival we were greeted by the host. She took plenty of time to show us around the property and explain how the bed-and-breakfast works and all the details of the winery brewery excellent day! Days of day."
United States
shawn
The price is AED 694
AED 764 total
includes taxes & fees
5 Dec - 6 Dec
Inn at Neshobe River
Front of property
Stay At Jimmy's

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Superb stay in all ways!"
United States
Scott
The price is AED 731
AED 804 total
includes taxes & fees
16 Nov - 17 Nov
Stay At Jimmy's
Front of property
Snowed Inn

Snowed Inn

3.5 star property
Killington
9.8 out of 10, Exceptional, (370)
"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!"
United States
Bradford
The price is AED 757
AED 916 total
includes taxes & fees
3 Dec - 4 Dec
Snowed Inn
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi
The Vesper

The Vesper

3.0 star property
Woodstock
9.2 out of 10, Wonderful, (44)
"The Vesper was a great find in Woodstock VT. Close to downtown to walk to everything. Rooms are spotless and charming. We would definitely stay at the Vesper BnB again."
United States
Kevin
The price is AED 565
AED 621 total
includes taxes & fees
17 Nov - 18 Nov
The Vesper
Front of property
The Vermont Inn

The Vermont Inn

3.0 star property
Rutland
9.2 out of 10, Wonderful, (412)
"The innkeepers were extremely personable, helpful and communicative. We will definitely stay again when we come to Vermont!"
United States
Anthony
The price is AED 744
AED 811 total
includes taxes & fees
16 Nov - 17 Nov
The Vermont Inn
Exterior
The Lilac Inn

The Lilac Inn

3.5 star property
Brandon
9.6 out of 10, Exceptional, (211)
"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! "
United States
Janet
The price is AED 824
AED 907 total
includes taxes & fees
20 Nov - 21 Nov
The Lilac Inn
Front of property - evening/night
Woodbridge Inn

Woodbridge Inn

3.0 star property
Woodstock
9.6 out of 10, Exceptional, (66)
"Amazing stay at a beautiful location. Would definitely stay again. "
United States
Aaron
The price is AED 1,634
AED 1,798 total
includes taxes & fees
11 Dec - 12 Dec
Woodbridge Inn
Outdoor pool
Echo Lake Inn

Echo Lake Inn

2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"The staff was super friendly, and welcoming "
United States
Janet
The price is AED 942
AED 1,027 total
includes taxes & fees
16 Dec - 17 Dec
Echo Lake 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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Top Pittsfield Hotel Reviews

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Loved the whole hotel staff was great and very helpful and it was very clean!!!"
Joseph 1-night trip
Posted 3 days ago
Hampton Inn Rutland

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 Vermont Inn: 16 rooms. 9 mi (14.5 km) from the downtown core. Enjoy the 24-hour fitness center and sauna. Snowed Inn: 19 rooms. Situated 8.9 mi (14.4 km) from the heart of Pittsfield. Enjoy the hot tubs and unique décor. The Lilac Inn: 9 rooms. 13.6 mi (21.9 km) from the heart of downtown. Enjoy the free cooked breakfast and unique décor. The Vesper: 9 rooms. Located 18 mi (29 km) from the core of Pittsfield.
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.