Pet-friendly holiday rentals in Stockbridge

A beautiful serene home set up with everything you need. We loved the space, both inside and out. There was a country store right down the road that had amazing food. Enjoyed relaxing on the deck after a great day of hiking. With so much hiking in the surrounding area, we are already looking forward to booking again.

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 !!!  

We had a great stay during our work trip to the Berkshires! Our toddler loved playing in the enclosed front porch and fenced in yard, and the crib and baby gates were such nice amenities for my peace of mind. Everything was clean and comfortable and we appreciated that Chamaio reached out to let us know when the home was ready for us, and gave suggestions on local spots nearby. We would absolutely stay here again if (hopefully when!) we are back in the area!

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.

Our family had a great time staying in Anneke’s house in Stockbridge; it had everything we needed and was very comfortable! The fenced yard was also great for our dog. Anneke checked in with us several times during the trip and was very responsive. Highly recommended!

For our fourth stay at Katie and Greg's, we were just as satisfied as the first x3 trips! And we're already planning our 5th! Truly a gem of a home and wonderful hosts. Highly recommend!

We loved staying here at Matthew’s Barn House. The location is not only peaceful and private, but we were able to completely unplug from our busy lives and enjoy time with our family.

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.

It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

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

Stephen's house is perfect for a long vacation or a weekend getaway. It has everything you need, and the pool is fabulous. My family and I had a great time.

The Eco Cottage was a perfect, tiny gem tucked away in the middle of the beautiful green woods. It was so private, peaceful, and serene. It truly felt like my own little retreat and since I was there to go on a retreat, this was the perfect place to lay my head at night. I loved walking the trails and wow, the pool, which looked so inviting (even if it was a bit too chilly to use this time!). Everything was clean, and the instructions were clear and easy to follow. Hosts checked in regularly but gave me my privacy. I really enjoyed my stay SO MUCH and will absolutely be booking here again the next time I’m in the area. Highly recommend!

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

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

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.

Picturesque location! Beautiful and peaceful ! Thanks for a lovely getaway! The WiFi was great and perfect for a day of remote working.

We had a great stay at Jaryn's place. We got to enjoy the pool and loved that it was so peaceful and private. The location was perfect, close to downtown Great Barrington. We slept comfortably and it was so quiet. We even got to see a bear driving down the main road!

Fin is an extremely warm and accommodating host. He goes out of his way to make his guests feel at home. Every time I stay at the Nest there are extra treats and goodies in the kitchen to personalize my arrival. I truly feel like family when I stay here. Fin adds a European bed and breakfast feel to this pristine 5 star retreat.

We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!

Beautiful little cabin, peacefully in the woods. Great, friendly, and responsive hosts. Perfect location to relax, walk around, find closeby hikes and hidden gems, including some great breakfast spots. 10/10 would 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!

This was a great weekend getaway for two of us. The apartment is pristine and private. It was a great base camp for outings in the Berkshires. Stockbridge is just one mile away up the road and has tons of cute shops and restaurants.