Pittsfield Travel Guide

Tourist Guide

A lake surrounded by autumn-colored trees and a rocky shoreline.
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
The price is £102 per night from 15 Nov to 16 Nov
£102
15 Nov - 16 Nov
includes taxes & fees
Stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Comfort Inn Rutland - Killington
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
The price is £115 per night from 8 Nov to 9 Nov
£115
8 Nov - 9 Nov
includes taxes & fees
Stay at this ski hotel in Killington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. Popular ...
The Mountain Inn at Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is £302 per night from 30 Nov to 1 Dec
£302
30 Nov - 1 Dec
includes taxes & fees
Stay at this luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (629 reviews)
"Fantastic stay at Woodstock Inn this week! The room and property were spotless, and the staff was incredibly kind and welcoming. The spa was beautiful, the food at Red Rooster was excellent, and the athletic center, pool, and hot tub were all great. The entire property has a quiet, peaceful atmosphere ..."

Reviewed on 6 Nov 2026

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.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
3387 East Mountain Road Killington VT
Stay at this ski cabin in Killington. Enjoy free Wi-Fi, free parking and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I ...
9/10 Wonderful! (70 reviews)
"It is a wonderful place to stay at any time for coming foliage or ski. The location is excellent, quiet and very clean inside. We felt like at home, We will stay again when we visit woodstook area next time."

Reviewed on 15 Oct 2026

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Loft for two with Hot Tub & Mtn Views

Cozy Loft for two with Hot Tub & Mtn Views

Granville VT
Stay at this cabin in Granville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Plush Quartz Art Glass - Glassblowing Studio & Gallery ...
10/10 Exceptional! (332 reviews)
"What a wonderful property! Perfect for a getaway! Thanks Jeff!!! Ps the hot tub was perfect on the chilly nights!"

Reviewed on 1 Nov 2026

Cozy Loft for two with Hot Tub & Mtn Views
Romantic Retreat:  Mt. Views, Hot Tub, Movie Theater

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Granville VT
Stay at this cabin in Granville. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. Popular attractions ...
10/10 Exceptional! (576 reviews)
"Wow, what a stay! We spent our honeymoon at this beautiful, cozy cabin, and it was the perfect romantic retreat. We loved cooking together, and the kitchen had absolutely everything we needed and more! The hot tub was perfect in the crisp autumn air, followed by snuggling up by the fire and watching ..."

Reviewed on 2 Nov 2026

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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.

Stay near popular Pittsfield attractions

Cities near Pittsfield

Explore a world of travel with Expedia