Pet-friendly holiday 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.

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.

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.

Had a lovely holiday week in Nancy’s home! We felt right at home. The home was cozy and beautifully sun lit in the mornings ! Nancy had decorated before leaving and it was adorable and sweet. The yard was amazing for my 2 large dogs - they ran around and found toys to play with. The area was walkable with sidewalks that were mostly cleared after the snow. Hilly for sure ! Good workout hehe Super close to MassMoCA and the center of North Adams. Walked a few times with the dogs. There’s a dog run near by as well. A short drive from Bennington, Pittsfield and a handful of ski resorts. We had a great stay. Friendly neighbors, communicative host and lovely surroundings :) would love to 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 property was fantastic. The lake is beautiful, the kayaks and canoe offered by Vincent were in great condition and easy to use to explore the lake. And the house is well decorated, comfortable, and fits a large group easily. I would highly recommend a stay. Vincent is a great communicator and made the whole process easy — zero hassle whatsoever along the way.

A beautiful, well-appointed, family-friendly place to stay. Teddy's place had everything we needed and more. The beds were comfortable, everything was clean and well maintained, and exactly as described and like the photos show.

Great place. As described. Met our expectations.

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.

We had an excellent experience with Todd and his cottage. It was a perfect weekend getaway. The space was very quiet and peaceful but close to local attractions. Todd had great recommendations for restaurants, shops, wineries, breweries, and other activities, all of which were no more than 10 minutes from the cottage via car. The space was small but appeared exactly as described in the listing. It was a perfect option for us and our dog. We would definitely return in the future!

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.

We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

the airbnb is very homey, well stocked, and easy to navigate. we had one slight issue with a mess that was not found by the cleaning crew, but robert was friendly and shared our concern about this.

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!

Everything was exactly as it was in the Description. It was a bit tricky finding the exact location reason being it was dark out when we arrived. However, Ann & Francois were great and responded quickly and stood on the phone with us and guided us until we arrived at the front door. all-inall it was a very pleasant stay and experience. We will definitely look forward to another visit. I recommend this place to all who enjoy these types of experiences.

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.

Jonathan's place was exactly what we were looking for in a Hudson retreat. We needed to base ourselves somewhere in the Hudson valley region and the location was perfect. Being less than 10 minutes to the town of Hudson, and 15 to Catskill, it could not have been more convenient. The home itself was pristine and they clearly put a lot of thought into the design as it has been newly renovated. All of the appliances were top of the line (stovetops, technology, sonos speakers etc.). Yet it was still very inviting. The home is stocked with absolutely everything you need. In fact it was one of the best stocked Airbnb's we had ever stayed in, and we've stayed in over 50! Jonathan and his partner live downstairs and were incredibly sweet. They are also very knowledgable about the area and very communicative. We would definitely be happy to stay here again and for extended periods of time, it certainly felt like our own little home away from home.

Collen's woodland lodge was a joy to spend a few days in. It felt like a family home, very cosy and extremely well equipped on all fronts. The location by the babbling brook was so pretty