Pet-friendly holiday rentals in The Berkshires

The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍

The place was super serene and peaceful—perfect for a relaxing getaway. The house was incredibly well maintained, clean, and cozy. Highly recommend to anyone looking for a comfortable and quiet retreat

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

What an excellent stay - this airbnb was incredibly well stocked with kitchen supplies, games, extra linens, really anything that one could want. Amenities were high quality and very thoughtful.

Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.

We spent the weekend in the area and Tim’s place was fantastic. It’s loaded with charm, comfortable and very well appointed and stocked (right down to treats for the dog). The location is beautiful and the views are amazing. Can’t wait to return!

This place is truly magical - there aren’t many place that offer you a private waterfall and creek for the weekend. If you’re looking for peace and quiet near the sound of a running creek and waterfall, this is the place!

Lawrence and Ilze are great hosts! They actually just live next to the house and they own a farm. We took our kid to visit their farms with lots of beautiful chickens and roosters. My son even has a chance to feed the chickens. We will definitely come back!

Our second time here. Great spot for our family of 4, and Sandy is very responsive

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.

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.

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

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.***

Only complaint would be the noise from road during the morning commute

Cody’s geodome was beautiful! We had a great weekend here and would suggest it to anyone else looking for a peaceful getaway with friends or family. The dome looks small from the outside but has plenty of space for guests. We never felt cramped. The kitchen has most of the essentials you’d need for a getaway. The highlight of the trip was the hot tub area with the mountains in the backdrop. The hot tub itself was amazing. Even with the rain, we still enjoyed being in there. We utilized the grill and the fire pit as well. Overall, a great stay, and we would love to go back again!

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.

Nicholas and Jenna are great hosts! We were beyond lucky that they shared their home with us! The views were great, so great that we eloped here! Cute cozy home pushed off the road with a beautiful view off the back deck! We would love to back to visit!

We were in Lenox to attend a reunion for the Lenox School for Boys ( Grad “66” ). The cabin was perfect for our needs especially because we could have our dog with us. Most of our time was spent with activities scheduled for the reunion so we didn’t really get to enjoy the peaceful atmosphere surrounding the cabin. There will be another reunion in 2026 so we will be looking forward to another stay at the Luv Shack. Thanks for sharing your abode. Pete & Becky Davis Mechanicsburg PA

Beautiful house and interior. The house was clean and well prepared. The basement is an entertainment hub. The weekend we visited was cold but the fireplace inside the house and fire pit outside made the weekend enjoyable and fun. Very pet friendly. Our dog had a great time exploring the woods while we in the hot tub. Amazing place to have a chill weekend with friends and loved ones.

The Yurt was great. Certainly a unique, off grid and mostly secluded experience. May not be every persons cup of tea if you’re seeking full resort accommodations. But if you’re interested in something different you won’t find everyday, this stay checks all those boxes

I know the area super well so have a good perspective on location and quality of available accommodation etc. Mark and Lori’s place was standout on all dimensions. Close to both Woodstock and Saugerties which is great for dining and social options. Location is safe, pretty, peaceful and convenient. The house itself is immaculate and charming with a lot of nice character touches. It’s well appointed, and even if you choose to dine in, they have supplied all that one could need. A special place and if I need accommodation again I would book in a heartbeat.

This is our second time staying at Foxfire Hill, and it was wonderful to see the gardens in their glory. Great and responsive hosts. I’m sure we will be back again.

Little Red School House was a pleasure to stay in and it was situated perfectly for our stay and needs. Beds are great. Location is GREAT!

We had such an amazing stay at the studio! The place was beautiful and clean. Nicole had awesome recommendations on things to do and they even had toys for our pup that we brought along. Would absolutely stay again and would recommend it to everyone!