Search Resorts in Pittsfield

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 4 Resorts in Pittsfield with updated reviews, rates, and availability.

Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 12+
Here's the main living area - dining is up on the left
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (109)
"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the time we left. Thank you David! We are looking forward to next year."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (449)
"Great place to stay and get away. Everything you need in a quaint location. Loved the hot tub, seats on the porch, and having the ability to use the projector to watch sports/movies!"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (194)
"Cabin was so wonderful, fire place was lovely right next to the hot tub. Host was great with communication. Very pleasant stay. Cozy, quiet, clean cabin."
Cozy Loft for two with Hot Tub
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.

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 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.

Recent reviews of Pittsfield hotels
Expedia verified reviews

The Shire Woodstock

The Shire Woodstock

5/5 Excellent
Comfortable and Clean
"Very comfortable bed, very clean room, fresh coffee in the morning, beautiful view of the river. Check-in was smooth and they kept in touch with us prior to arrival."
A verified traveler stayed at The Shire Woodstock
Posted 1 day ago
The Shire Woodstock