Vacation rentals in Pittsfield

What a wonderful stay my family and I had! With two small children it was so nice to be in walking distance of so much! My wife especially took advantage of the coffee shop next door! Would recommend to family and friends and plan on booking again next year!

Very nice place. Great for a family getaway or a gathering with friends/couples. Most bedrooms have attached bathrooms which was great. Game room was very fun. Fooseball table is broken, so if you’re a rare foose junky like myself don’t plan on it. Only disappointment in this great home. Make sure to bring towels or you’ll be taking a trip to Walmart. Otherwise Highly recommend

Hillary's place was a wonderful place to stay for a cozy weekend getaway. It felt very homey with personal touches. We were here during a little snowstorm so we didn't spend any time outside but the yard and private deck were really nice. We had some troubles with the hot water but Hillary was very responsive and helpful! We would definitely stay here again.

Very nice place to stay right by South Peak. Whole place very clean and great amenities. Rick was extremely kind and helpful, above and beyond as a host!

First time staying at Scott’s NH North Conway home, and it went very well. He and his team were very responsive to any questions I had and the area was a short drive away. The location of the house was a little confusing to find at first but once we realized it was tucked away, the check in process was easy. The house was great for what we needed for the stay. Thanks!

I’m grateful that Peggy and Harry were willing to rent to us at the last minute. Our family needed a quiet respite to be together during a difficult time of loss. The solitude of the lake and woods was calming and we had plenty of room to be together. I only wish we could have stayed longer!

We had a delightful stay at Matt's and Jenn's. Their cottage is warm and cozy (loved the oversized fireplace), with spectacular views. And while there are many homes nearby, it has a real sense of privacy. The kitchen has almost everything you need (although some good wine glasses would be nice) and the appliances are high quality. We found the beds, with their medium-firm mattresses, very comfortable and we slept well. The wi-fi was excellent and the TV and thermostat didn't require a PhD to operate. Very simple and intuitive, unlike so many properties. Plus Matt and Jenn were very responsive to our queries (and they didn't have onerous check-out requirements, again like so many other Airbnb properties). We would definitely return, particularly in the off-season, but then spring and autumn are our favorite times of year. Highly recommend.

Ricky’s place was amazing! Fabulous location just a 10 minute drive from the Franconia Loop Trail (where we hiked). Big studio apartment with a full kitchen & bathroom. Very cute woodsy decor inside & there is a lovely common area in the apartment with board games & and a fire for after dinner activities! We had such a great time!

We were a group of 10+ women ranging in ages from 16 to 60 something. Moms, sisters, cousins, aunties and long time friends gathering for our annual “girls weekend”. A tradition spanning over 30 plus years, our group’s dynamics may have changed a bit - but not our excitement of coming together once a year. For the size of our group we require some standard needs: enough beds to sleep comfortably, enough bathrooms to accommodate all of us, a decent size cooking area, plenty of room for us to be social and room for all our vehicles. The Honey Bear House checked all those boxes. Kerri was very attentive to us, checking in on us at the start of the weekend and quickly responding to our texts. The house was as she describes it, plenty of dishes, silverware, cooking utensils, pots/pans, bowls & appliances, toaster & toaster oven, drip coffee & Keurig, lots of mugs! We supplemented with paper products & personal towels. Perfect spot for an extended family gathering!