A lake surrounded by autumn-colored trees and a rocky shoreline.

Search Resort Hotels in Pittsfield from CA $497

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Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Pittsfield resorts

The Jewel | Living area

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (121 reviews)
"Excellent stay "
United States
Kristen
The price is CA $456
CA $497 total
includes taxes & fees
Aug 10 - Aug 11
The Mountain Top Inn & Resort
Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (591 reviews)
"As always - best hotel in Vermont."
United States
ben
The price is CA $673
CA $802 total
includes taxes & fees
Jul 20 - Jul 21
Woodstock Inn & Resort
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

Brandon Inn

Brandon Inn

10/10 Excellent
"The property was excellent. Very old inn well maintained, looks almost new. I'd recommend it to all. There is an elevator but is operated by the staff. Old style manual controller."
allen 1-night trip
Posted 3 hours ago
Brandon Inn

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
712
Accommodation
2 Resorts
Lowest Price
CA $497
Highest Price
CA $802

Frequently asked questions

What is Pittsfield like for a resort vacation?
You deserve to get away, and a resort is the ideal place to pamper yourself with the services and amenities you need for a relaxing stay in Pittsfield. One of the comfortable resort hotels in the surrounding area could be just what you're searching for, whether you want great restaurants on site, blissful spa treatments, or fun activities to try.
What's a top resort for my stay in Pittsfield?
Here are our top-rated resorts near Pittsfield: Woodstock Inn & Resort - Luxury resort. 17.9 mi (28.9 km) from Pittsfield. Features 4 restaurants, 2 bars, and a golf course. The Mountain Top Inn & Resort - Beach resort, 5-minute walk from Green Mountain National Forest. 6.9 mi (11.1 km) from Pittsfield. Has a private beach, ski-in/ski-out access, and a seasonal outdoor pool.
What can I do in Pittsfield?
Green Mountain National Forest, Roger Clark Memorial Central Library, and Pittsfield Town Hall are a few of the interesting sights to visit. Other attractions in the area include Liberty Hill Farm and Green Mountain National Golf Course.
What's the seasonal weather like in Pittsfield?
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's the best way to get to and around Pittsfield?
Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) away from the heart of the city. You can also search for flights into Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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