Holiday houses in Pittsfield

Judy was a great host, very gracious and the place is beautiful. We loved walking around the area and would love to come back!

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.

Gisele and her property manager were promptly responsive. The cottage was extremely clean, newly decorated and well appointed. The layout was very comfortable for our family of four. The pools were nice and not overly crowded. The only negatives were: If not taking the trolley or golf cart, the closest pool was a half mile walk with no parking available. The further pool did have parking. Also, no outside water source/hose to rinse off. Plenty of restaurant choices nearby in Wells, Ogunquit and Kennebunkport. Wells beaches were beautiful with easy, affordable parking. Overall a wonderful stay in Wells!

The Best palace

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.

My husband and I stayed at Kristen’s apartment for 2 weeks at the end of August and had the most amazing time! This was our 3rd time to KPT and most definitely our favorite thanks to this gorgeous Airbnb and Kristen’s hospitality. The apartment was perfect for us — was exactly as described, better than the photos with amazing windows and views, speedy WiFi perfect for working remotely. It’s a quick 4 minute drive into town, and such a beautiful area to walk around. Kristen was so responsive and helpful — there’s a super extensive list of local reccs in the apartment, and a beach pass that you can use during your stay. We loved this home away from home, and can’t wait to come back soon!

We had a great long weekend at Northern Lights! The space is very clean and comfortable, making the most of every square foot. When we had a hot water issue, Sal was on the scene within minutes to fix the problem. Would definitely stay again!

We had a wonderful weekend celebrating St. Patty’s Day up in Ogunquit. The property was everything we had hoped for in a rental. Everything was comfortable and clean. The house is spacious and a great place to get your day started. You can’t beat the location! Off the beaten path, but a few minutes of walking to downtown. The host was super responsive to my questions. I would absolutely stay here again.

Fantastic location. Very nice house with beautiful design. Chuck was very accommodating and communicated well. Super kind hosts.