Pet-friendly holiday rentals in Pittsfield

We had the BEST TIME at this fantastic Lakeside house in Valatie!  The house itself has 3 good bedrooms – 2 large bedrooms upstairs with a nice bathroom and tub.  The downstairs has the other cute bedroom, another full bathroom,  a good sized kitchen open to a great and large living and dining area. The VIEW from the main room is stunning and was our ‘TV’ for the week.  The lake is just gorgeous!  It has a little dock with kayaks and plenty of nice seating and lounge chairs.  It’s great to have a full grass lawn !  The pups loved the house and the yard and the lake!  The house was super clean and roomy but cozy in it’s feel.  So many great little towns nearby – it was just the perfect house to get away from the city!  The community was chill, even tho it was Memorial Day weekend.  Thanks to Michael who was super responsive (not that we needed anything!) but if we had a question. Etc.  Thank you Michael ! We hope to be back for another visit !!!  

Great stay! Thank you so much.

Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.

Alfredo's home was more peaceful than the photos could show. it was quiet, secluded and clean, inside and out. being close to stores and the town while having the feeling you're farther away from society was just what was needed for the stay.

Great location. Close to North Adams and Rt 2. Perfect set up for a family gathering. Several common rooms to enjoy together.

We stayed here for the weekend of our son’s graduation nearby, and it was the perfect place to land. The house is beautiful and full of charm, with original artwork, comfy chairs, and inviting spaces to gather and relax. You can really feel the care and attention the hosts put into making it special. Thanks to a stretch of spring rain in the area, the landscape around the stone house was vividly green, lush, quiet, and full of life. One of our favorite moments was sitting on the bed and being surprised by a hummingbird visiting our window. Such a lovely and memorable stay!

Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family

We enjoyed the perfect escape from the city in this magical barn with gorgeous antiques and pristine views. Definitely will be back for future celebrations!

Even in the rain, this was the perfect getaway! A mix of summer camp and mountain cabin vibes made it feel warm and welcoming

Very nice place, beautiful big deck, awesome creativity to the lighting around the property. A walking path, fire pit, hot tub, big deck to relax on, and a fully equipped stage. It is a step above camping but not quite glamping. A lot of fun, and Apple is a sweet bonus hostess.

Robert was an excellent host. Proactively reached out with help to find the home, and a whole host of recommendations. Great space, very private, and had everything you could need.

Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

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!

We really enjoyed our stay, it was perfect distance from family and friends. Would highly recommend this place.

We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.

Everything was what we expected. Very clean and organized. Hot tub was awesome. Great yard. Mattresses could have been more comfy but weren’t terrible. Overall it was a perfect weekend and we would definitely go back! A great choice!!!

Wonderful place on the lake with a great host. Janice was very responsive, offered an early check-in and set up a baby gate. Great place for dogs and kids.

What more could you want? This quaint cabin situated in the woods offers privacy, unique architecture, comfort, and peace. It’s equipped with everything you could possibly need, and the hosts were truly some of the most responsive and kind people I have ever interacted with. They truly went above and beyond for us. We stayed with a toddler and two dogs, and they all loved the property and the cabin. We will most definitely be back!

Highly recommend Brian’s off grid cabin! His directions were very helpful and made navigating the generator, camp shower, and other on-site details super easy to understand and execute. His property is beautiful and peaceful. We’re already looking at our calendars for another time to visit. Our dog, Stumpy, very much enjoyed the outdoor access and pond. He didn’t want to leave!

The Hygge House was a lovely spot to spend my birthday weekend with my family and friends. We took advantage of so many close-by activities. But the highlights were at the house itself - paddling the canoe and kayak through the water, outdoor dinner, and s’mores at the fire pit. Jessica was also so easy to communicate with and super accommodating during a personal emergency we experienced. We loved our stay and would love to come back again soon.

Our company stayed at Deborah and Ashley’s for 10 days and we had a wonderful stay. We were incredibly comfortable and there was enough room in the house to find separate work space as well. Highly recommended would stay again and D and A were fantastic at communication. 5+!

My wife, dog, and I had a wonderful and peaceful stay at Michael's place. The land is beautiful, the place itself is actually even nicer than the pictures, and there is plenty to do in the area. We will definitely be coming back!

The space is luxurious and stunning even more beautiful than the photos, so thoughtfully designed and really helped us feel at home at once. Matt and Sarah were so helpful whenever we had any questions. We had such a relaxing stay and feel so grateful to have been able to enjoy the space!