Search Chalets in Pittsfield

"Awesome property and very responsive staff! Highly recommended. "

"House is beautiful, well stocked. Kat was exceptional as host; all my questions were promptly answered. Location is ideal"

"Took a week long vacation with friends and this was the perfect place for us. A lot bigger than we had anticipated, equipped with every we needed and only a short 10 minute drive to Killington. The only issue we had was the wifi. We didn’t have any reception but luckily none of us needed to check in with work."

"Great location close to Killington Ski Resort, about 8min drive to snow shed/ramshead. House was perfect for our group of 16. Plenty of space & bathrooms! Hot tub was great after long day of skiing & snowboarding. Herbie was quick to answer all our questions. Can't wait to go back next year!"

"This property is really nice and spacious. It is perfect for three couples as each bedroom is on a different level. It kept really warm and cosy, the kitchen is well-equipped and the games room is a real bonus! The location is great too - just a few minutes drive to the Killington base lodges - however one slight drawback is that it is right next to a main road and at night you can hear cars going by (not super loud though and not really a problem). Overall we really enjoyed our stay and we...

"The house is amazing. The hosts clearly love it, and it shows in how well it is set up and stocked. Highly recommended."

"excellent house- very close to sugarbush "

"“We had a wonderful time staying here! The view was absolutely beautiful, and we truly enjoyed the peaceful setting. The kitchen could use some upgrades—some of the cookware was worn, and the oven needed a little extra cleaning. If you plan to cook a lot, bringing a few favorite pots might be helpful. That said, the location and overall experience made for a great stay, and we would love to visit again!”"

"Great quite location near restaurants and 5 mins from the slopes. The kids loved the little arcade area and the hot tub was great for after skiing. Furniture was a little outdated but met our needs for a fun family vacation"

"We stayed at the overlook for a family ski trip. It was the perfect place for our family of 4 with 2 young kids. The house was well appointed and what we expected, our hosts communicated well and it was an easy drive to killington mountain every day to ski."

"Nice & comfortable Great location between Killington & Okemo"