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21 Nov - 23 Nov
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28 Nov - 30 Nov
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12 Dec - 14 Dec
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9 Jan - 11 Jan

Resorts in Pittsfield

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, (93)
"We had a great time! Gorgeous view and everybody was super friendly and helpful!"
United States
Courtney
The price is AED 867
AED 945 total
includes taxes & fees
18 Nov - 19 Nov
The Mountain Top Inn & Resort
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (549)
"I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn"
United States
Kevin
The price is AED 1,208
AED 1,491 total
includes taxes & fees
16 Dec - 17 Dec
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

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"Nice! "
Michele 1-night trip
Posted 1 day ago
Sleep Woodstock Motel

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. 6.9 mi (11.1 km) from Pittsfield. Has a private beach, ski-in/ski-out access, and a seasonal outdoor pool. On The Mountain - 1 - Bedroom - Sleeps 6 - Located right by Killington Resort. 10.1 mi (16.3 km) from Pittsfield. Enjoy the fitness center.
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 Gifford Woods State Park and Pico Mountain at Killington Ski Resort.
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.