Search Resorts in Pittsfield

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Compare 2 Resorts in Pittsfield with updated reviews, rates, and availability.

"All staff were friendly and helpful. The room was spacious and comfortable. We took advantage of the spa on premises, and though everything was pricier than were used to paying, the spa and 3 night stay - very enjoyable."

per night

May 27 - May 28

Seasonal outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas

"Beautiful property! Friendly staff . Great location. Very quiet Stayed here for ski trip : Stratton and Killington will come back to explore the property "

per night

May 17 - May 18

Other property types in Pittsfield

"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "

"Will be back!!"

Pittsfield Resorts information

Number of reviews	481
Accommodation	2 Resorts
Lowest Price	NT$9,691
Highest Price	NT$10,461

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.

What can I do in Pittsfield?

If you’re interested in local sights, Appalachian Trail Adventures, Green Mountain National Golf Course, and Gifford Woods State Park are some places to visit nearby. Other attractions in the area include Pico Mountain at Killington Ski Resort and Killington 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 April, 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.