Pet-friendly holiday rentals in West Stockbridge

Our group of 5 were very happy with our stay in Lenox. Location was perfect in that it was close to everything we had planned in the area. Everything went very smoothly in booking the rental and all the communication involved. The place was very nice.

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 !!!  

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

No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

We enjoyed our stay at the house. Mitchell was very responsive and communication was easy. The house is near butternut and GB. Hopefully we will come back in the summer to enjoy the outdoors.

Beautiful area and beautiful house – well-designed, spotless, and equipped with everything we needed. It looked even better in person than in the photos. The open family area was amazing and spacious. We also had a lot of fun exploring the farm and surrounding property. Definitely one of the loveliest Airbnbs we've stayed at. Highly recommend!

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!

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

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.

The house and property were absolutely lovely, clean, and peaceful. We had everything we needed. When there was a big rain storm and the internet had some issues, the hosts responded immediately and reset the modem and offered to call Spectrum. Issue was fixed right away. The pool was perfect temp and so restorative. Would 12/10 recommend staying here.

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!

Very clean. Well furnished kitchen. Spacious. Good value.

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.

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Had a beautiful stay and would 100% return and tell friends about it. Cute and cozy stay, lovely little town and beautiful views.

The house was beautiful and very family friendly. They greeted us with milk, orange juice and a carton of eggs in the fridge. They even had a selection of beer testers for my husband to try. We had an issue with the pool heater not turning on and both host were very helpful and responsive. I loved the hand drawn map guide they made me when I could not locate something ! They even got someone out there that same evening. Especially on Memorial Day weekend I was impressed on how quickly. I would definitely recommend this home to anybody and will go back if I’m ever in the area again.

A lovely break from the city - which is exactly what we wanted. Our dog loved it too. The barn is spacious and well appointed and the grounds are perfectly maintained.

This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.

Lisa’s place was wonderful, and I highly recommend it. She was very responsive to questions, and I appreciated the helpful notes around the house. The space was thoughtfully made dog-friendly, with couch covers that kept things worry-free. The garden was beautiful, and the property offered great outdoor spaces—a back deck, a front grill with seating, and a creekside trail (not fully cleared, but enjoyable). My dog and I loved it. We stayed on the top floor and loved the airy living room with high ceilings and skylights. Lisa’s nature-inspired decor on the desk and fireplace mantle added charm. The bedroom was spacious, and the extra-large bed was incredibly comfortable. The house having three bathrooms was a nice bonus.

This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!

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!

We had a wonderful stay! Our family really enjoyed this beautiful home. The house decor/art work was fantastic, the home was warm, welcoming and very spacious. There was plenty of room to spread out and everything was very clean. The outdoor space was beautifully done and was perfect for hanging out/grilling. Would highly recommend!

Great stay! This is our second time staying at Bradley’s place and it was exactly the same as last time, in a good way. Place was clean, great neighborhood, very quiet!

Matt and Sarah’s place is wonderful. A great place to relax and enjoy the beautiful surroundings. The house is just as described and the hosts make you feel right at home. We hope to come back again!