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

Best Resorts in Pittsfield

Check prices for these dates

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9
In one month
Aug 21 - Aug 23
In two months
Sep 18 - Sep 20

Our top choices for Pittsfield resorts

The Jewel | Living area | TV

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
$325 nightly
The price is $354
Jul 27 - Jul 28
Total with taxes and fees
The Mountain Top Inn & Resort
Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (592 reviews)
"As always - best hotel in Vermont."
United States
ben
$471 nightly
The price is $519
Aug 2 - Aug 3
Total with taxes and fees
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"This property is liking being home. Everyone was very helpful and welcoming. I needed to call the desk twice for something and they were at my room with what I needed in minutes. The one thing I would let others know is it is an older building so no elevator. It was a bit of a struggle for this 68 year old to lug my bags up three flights of steps especially since I was exhausted from my seven hour drive to get here from Pennsylvania. E still very much enjoyed our stay and the morning continental breakfast and readily available free bottles of water."
Karen 4-night trip
Posted 16 hours ago
The Mountain Inn at Killington

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
713
Accommodation
2 Resorts
Lowest Price
$354
Highest Price
$519

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 Green Mountain National Golf Course and Gifford Woods State Park.
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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