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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Pittsfield bed & breakfast

Exterior

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (194 reviews)
"Superb stay all the way around! Mike and Barbara work very hard for their guests and it shows with all the room details and breakfast is 5 out of 5 stars everytime. Check in and out is very easy as well as parking even on snow covered days as the property is very well kept and cleared. Loved it and want to return!"
United States
Steven
The price is AED 404
AED 457 total
includes taxes & fees
19 Jan - 20 Jan
Mountain Valley Retreat
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (261 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (375 reviews)
"A wonderful hotel. The atmosphere is warm and clean."
United States
Fevzi
The price is AED 784
AED 949 total
includes taxes & fees
20 Jan - 21 Jan
Snowed Inn
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (415 reviews)
"Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗 We would stay here again. "
United States
Jodie
The price is AED 942
AED 1,027 total
includes taxes & fees
19 Jan - 20 Jan
The Vermont Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is AED 636
AED 700 total
includes taxes & fees
28 Jan - 29 Jan
The Vesper
Exterior

The Lilac Inn

The Lilac Inn
3.5 star property
Brandon
9.6 out of 10, Exceptional, (213 reviews)
"Clean, quaint and lovely! Great service and located in a cozy little town. "
United States
Jessica
The price is AED 808
AED 888 total
includes taxes & fees
4 Feb - 5 Feb
The Lilac Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46 reviews)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is AED 915
AED 1,006 total
includes taxes & fees
19 Jan - 20 Jan
Stay At Jimmy's
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98 reviews)
"No lake-view. Friendly staff, excellent breakfast."
United States
Wendy
The price is AED 1,006
AED 1,097 total
includes taxes & fees
20 Jan - 21 Jan
Echo Lake Inn
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is AED 1,215
AED 1,336 total
includes taxes & fees
19 Jan - 20 Jan
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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Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Check in service Breakfast"
Dustin 1-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. 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 Vesper: 9 rooms. 18 mi (29 km) from the heart of downtown.Mountain Valley Retreat: 2 rooms. Located 6.3 mi (10.1 km) from the core of Pittsfield. Enjoy the free full breakfast 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.