Apartment holiday rentals in Pittsfield

Rachel was an excellent host! She communicated with us immediately whenever we had a question. Her home was so comfortable and welcoming. We were up in the area for a wedding and most of the guests stayed in a place that was double the price! It rained constantly the entire weekend and we were so grateful to have a "home" to relax in between wedding activities. It was spacious, clean yet felt very warm and cozy. I loved the artwork and furnishings, as we have an appreciation for antiques. Rachel left us great coffee, oatmeal and even half and half in the fridge ❤️! She even aplogized for the rain! We would definately stay here again or recommend to friends. Thanks for making our cold, wet weekend and bit better!

Have stayed here before. Will stay again. Fits my needs and Shahs a great host

This is a wonderful space, lots of natural light, comfort and Shayla thought of everything for the kitchen and bathroom, which includes a handy washer and dryer. I felt so at home here and the location was steps away from coffee shops and a local bookstore, as well as a short drive to Tanglewood. Shayla was always available as needed, but also gave plenty of space. She was a superb host! I hope to return again soon!

I had simply the best time--the nicest people, a beautiful apartment, an absurdly good value, and a great location for exploring western Mass. I'm looking forward to staying here again next time I'm in this part of the country. Do yourself the favor and choose this one, you won't be disappointed.

Can’t say enough good things about this find near Jiminy Peak in the Berkshires! Stayed for three nights while skiing two days over presidents weekend. Hosts were very thoughtful and flexible. Left cookies and s’mores kit which were a nice touch. During snowstorm steps to the unit and walking areas were kept shoveled and salted. For us and our two teenagers this offered the perfect alternative to pricey on mountain lodging and was only about a 13 minute drive. There was even a bonus game room which could probably serve as a small additional bedroom if someone had the need, it certainly has room for a twin air mattress. Our two kids shared the queen bed with minimal fighting, but that would’ve been our back up plan😂. Anyway, they were super responsive, check in and check out was easy and will certainly look to stay again if we get up there to ski again this year !

The apartment is cozy and lovely! My mom and sister visited for my graduation and it was amazing for their 1-week stay. I was initially worried that the property will be a bit noisy at night because it is in a busy area, but it was actually neatly tucked in behind a closed business — really private and quiet. Kim is also very responsive as a host!

Ivy on the Stone is a gem. We will definitely return. The bed was very comfortable, the bathroom large and there is even a large screened porch for relaxing on comfy chairs, a sofa as well as a table for eating. Area restaurants are great, walkable to coffee shops and a large bakery in addition to a charming downtown with boutiques etc. Katherine is extremely attentive and we plan to return. MOST HIGHLY RECOMMENDED!

Amy is a fantastic host and has thought of everything you need while staying here. It’s convenient to everything in town and feels like home.

My family and I were in town for my annual fall birthday getaway and had a pleasant stay! Melissa’s place was clean, easy to find, and had all the right amenities. We would be glad to stay here again for a future visit.

Tracy has created such a warm, charming space. Tastefully decorated with attention to every detail. I couldn’t have been more comfortable or pleased.

My stay at Yina's was perfect for what I was looking for. The space was cozy and quiet and that bed was so comfortable. There was a nice work space with a refrigerator as well which was convenient. Yina and Katelynn were quick to respond to messages etc.

This couldn't be a more perfect location. Walkable to everything and centrally located. The apartment itself was beautiful as well.

Apartment was very spacious and comfortable. Nice and quiet neighborhood. Convenient location to hiking trails. Would stay again.

Teresa was a great host! she was helpful in communication for our arrival and stay. her place is truly the sweet place! so clean, comfortable and beautiful! thank you!

Our stay was fantastic - it was a lovely property in one of our favorite neighborhoods. The apartment had all the basics you need, along with thoughtful touches. Thank you for such a great getaway!

Second visit here . It is comfortable clean and very well organized . We enjoy it a lot . The kitchen is easy to use. Our Grandaughter was able to cook a wonderful supper for us.

A great place for a skiing getaway at Jiminy Peek Resort! Ski - in, ski -out, a lovely appointed condo, with access to a hot tub. Frank was most helpful and friendly. I highly recommend his place.

Accommodations were perfect. Very comfortable. Ski on ski off the mountain and close walk to the lodge and restaurants!

My stay was smooth and the condo was nice. I was on a business trip so I didn't have much time in the room besides sleeping which was quiet

We enjoyed our stay immensely! Great location and beautiful place. Our hosts were also fantastic. We would love to go back!

The absolute perfect location at the heart of the Berkshire Yoga Festival! Loved the location. Very comfortable for two people. The host was very quick to respond and was accommodating. I would definitely recommend and would stay there again.

Theresa was an amazing host, she clearly communicated with us along the way, and made sure we had our privacy & provided the upmost comfort. Her space was well kept and full of considerate touches to facilitate a relaxing stay, the subtleties go a long way. We enjoyed the hot tub in the snow, shared a few stories of skiing adventures & loved the friendly visits from Ben. The views were picturesque to boot, we definitely plan to come stay in other seasons.

This was my second stay. Great for a family of 3 and a dog that doesn’t mind a flight of stairs:)

Good location, very clean and spacious bedrooms and bathrooms, quite neighborhood, easy communications with host... a wonderful place to stay while enjoying the Berkshire ..