Search Resorts in Pittsfield

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Check prices for these dates

Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul
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1 Aug - 3 Aug
In two months
29 Aug - 31 Aug

Resorts in Pittsfield

Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (521)
"Relaxing "
The price is SAR 1,609
SAR 1,935 total
includes taxes & fees
6 Jul - 7 Jul
Woodstock Inn & Resort
The Mountain Top Inn & Resort
The Jewel | Living area | TV

The Mountain Top Inn & Resort

3.5 star property
9.0 out of 10, Wonderful, (84)
"Great views and food. "
The price is SAR 1,219
SAR 1,528 total
includes taxes & fees
6 Jul - 7 Jul
The Mountain Top Inn & Resort
Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA
Exterior

Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA

Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA
On The Mountain - 1 - Bedroom - Sleeps 6
Pool

On The Mountain - 1 - Bedroom - Sleeps 6

On The Mountain - 1 - Bedroom - Sleeps 6
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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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. Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA - 8.9 mi (14.3 km) from Pittsfield. Enjoy the hot tub. On The Mountain - 1 - Bedroom - Sleeps 6 - Located just steps from Killington Resort. 10.1 mi (16.3 km) from Pittsfield. Amenities include a 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 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.