Pet-friendly vacation rentals in Pittsfield

This was the second time staying in this house with another family. Can't beat the convenient location to local mountains for skiing. House is spacious and plenty of room for two families of 4. Shiyrah is friendly and communicative.

We had the absolute best stay at Jeanie’s home! It was beautiful, spacious, and so well decorated, and the property couldn’t be more peaceful. The chickens and ducks in the backyard were so fun to watch, and really made the stay so magical. Jeanie was so helpful too, with lots of local recommendations and made our whole trip so easy! The house oozes with charm and character, and we couldn’t have loved it more!

Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.

Great stay. Very quiet and peaceful. Place was immaculate on arrival.

we stayed for the Thanksgiving holiday to have more space for family and friends to visit. this was definitely the nicest Airbnb we have stayed in and would highly recommend it if you plan to stay in the Berkshires. you are within minutes to everything you might need but secluded enough for you to feel like you're the only ones there. we loved the fire pit and the house is spacious and beautiful. the house had some really neat features as well such as the old antique music box was super cool and played with the most amazing sound. we will be back.

Comfortable house with a lot sun, big fenced back yard and great vibes. Luis was available for any questions and the neighborhood was quiet and felt safe. Thank you!

This was a great time. The house is on the same block as three restaurants, a coffee place and a bakery. So, most days, it was easy to walk for three minutes and get something to eat/drink. The dog was happy because the house was so close to the creek, in addition to large fields w/in walking distance. I also drove a decent amount, because I visited Athens, Hudson, Saugerties, Woodstock, Tannersville and other nearby towns. Emily's and Carol's house is within twenty minutes of a ton of places. The house is simple and had what I needed - a strong heater, two comfortable bedrooms, two baths, and a large table that accommodated my laptop, monitor and keyboard. Finally, during my month-long stay, I had a change of plans, and Emily & Carol were very helpful and understanding about the necessary re-arrangement. It was a great place to stay.

We enjoyed our stay. The house is very cozy and clean. The backyard was my favorite part, since we were travelling with our dog and he very much enjoyed freedom in the yard and a nice weather! The area is very peaceful and quiet.

We had a fantastic stay! Our group of 8 adults, 1 toddler, and 2 dogs had an amazing time. The house was spacious, clean, and comfortable—perfect for a family getaway. Vincent was an incredible host—attentive, thoughtful, and quick to respond to anything we needed. He even had small trash bags delivered when we asked, and followed up when the delivery had an issue to make sure it was corrected. One of the highlights was the binder he provided, which was full of helpful information about the house and local area—it really helped us plan our stay. The kitchen was another standout: impressively stocked with basics like flour, sugar, and salt, plus a KitchenAid mixer, toaster, coffee maker, food storage containers, multiple cutting boards, and lots of serving ware. It made cooking for our large group so easy. We felt truly taken care of the entire time. Vincent’s hospitality made all the difference. We’d absolutely love to stay here again!

Pictures don’t do justice! Craig’s place was lovely, from the amazing kitchen to the spacious living room and the outdoor patio. For a group getaway this is the perfect place. Would stay here again in a heartbeat!

Lovely and relaxing stay. Easy to find and very clean. We loved using the kayaks too!

there was lots to do inside the house as well as outside. everything was amazing

This was my third time staying on Rosalind's property, but my first time in the "retreat" unit. The space is better in person than in the photos! It's a spacious two level unit with a huge bedroom/loft type area, perfect for setting up your yoga mat! The high ceilings and large forest facing windows in the bedroom were a highlight for me. Rosalind has always been a very responsive, thoughtful, and flexible host. I can't wait to stay again!

Leo and Michelle were very responsive with any questions we had, and even reached out to offer us an early check in. The location was close enough to our places of interest, while still being slightly rural. The place looked just like the pictures and we felt right at home. We will stay there again when we return!

Tina’s place is fabulous. The modern decor and architecture is beautiful. The location is peaceful and the fenced in yard was amazing; our dog loved roaming around and exploring. The outdoor space is great for grilling and sitting around the fire pit. We especially loved the kitchen. It is fully appointed and the kitchen island is incredible for prep and serving. The washer dryer combo was an excellent touch and we were able to do a couple of quick washes so that everything was clean and ready to unpack at home. Saving the best for last; the soaker tub in the master bedroom is luxurious and relaxing. Thank you, Tina. We can’t wait to visit again soon.

House was very clean and comfortable. Loved the decor and bed was super comfortable and cosy. Everything was there in the house- kitchen, bathroom, hot water. Well styled decor. Spotless. Felt very private and peaceful. Location was not as picturesque as I prefer, but fairly close to sight seeing.

What an amazing place to visit Vermont. I had a great time at the little red house. The place is beautiful and quiet. It is a 12 min drive to Mount Snow. Joe has a bunch of classic DVDs and we enjoyed some of them during our stay. The place is very clean and there is warm water and WiFi.

Gatherwild and the Shasta vintage camper was the perfect escape from the craziness of the city. I couldn't have picked a better, more peaceful place to relax, listen to nature, and stargaze. The camper is quaint but very well-kept and clean and there was more than enough room and storage for myself and my pup. Everything at Gatherwild feels very intentional and it feels like Laura has thought of everything–I didn't want to leave at all during my stay because I wanted to enjoy everything that the grounds had to offer. The bathrooms were super clean, the kitchen well-stocked, and the feeling of community surrounded the ranch. I was very sad to leave and can't wait to visit again, perhaps in fall, and stay in the camper again or even one of the beautiful tents!

Stayed at Val's place for 4 months. We were very happy here, it's extremely spacious and the furniture is very comfortable. Plus, it has everything you will ever need during your stay from a screw driver to cheese grater which is often hard to find in rentals and you end up having to buy extra supplies if staying for an extended period of time like we were. The Location is perfect, a few minutes walk to Warren Street and 5 min drive to Fairview Ave. Host is so helpful and responsive. Five + stars. Thank you Val!

The loft was lovely: fireplace, large balcony, view down the mountain, TV with airplay support, kitchen, etc. the surrounding was quiet and peaceful. The host was responsive and very friendly. Would recommend to others.

It was very peaceful, great get away from the city. Good for the dogs. The copper tub is amazing, we could not get enough of it. And the dual showers felt so good. It felt very homey. Mr. John was a a great host.

This was a very private and peaceful place to stay. Sourabh was a great host who was attentive and made the process smooth and easy. The dome house allowed for amazing views of the stars and the woods. If you want a peaceful and quiet getaway from the city, definitely come here.

The stay itself was wonderful! As advertised, it was well within walking distance from the downtown area, was cozy, and looked exactly like the pictures showed. 5/5 stars What pushed it over the edge from a good Airbnb to GREAT, was the attention Jennifer paid to small additional details - little chocolates to welcome us, snacks intentionally set out for us, water bottles, and a few other things speak to how good of a host she is. 6/5 stars 5/5 stars for Jennifer and her lovely apartment, 3/5 stars for Airbnb: we didn't get a message from Airbnb until we were checking out that her messaging wasn't working, so a couple messages went unanswered. Jennifer had put her number in 3 different locations explaining this, so she was super proactive, we were just a little unobservant in seeing that.

Joe was a wonderful host who provided a wonderful, clean space. I would recommend it to anyone looking for to stay at a cozy location for the evening. Thanks!