House vacation rentals in The Berkshires

This property was an amazing value! Jennifer and Jose were incredibly communicative even before I checked in, with a full on local guide sent to me before our group arrived in Bushkill. And when issues arose during our stay they were helpful and understanding. It is a beautiful property with plenty of space for everyone. Clean bathrooms, immaculate kitchen - everything just like the photos. Can’t recommend this place enough.

We stayed as a family of 4, including a 1 year old and 3.5 year old. The place was extremely comfortable and had everything we would need for our stay. The kids enjoyed the playroom and kids room with lot of toys and books. Kitchen was fully stocked with plates, utensils, cooking ware, and a high chair. Place could easily accommodate more people, very clean, comfy beds. Property manager was very responsive. Short drive to downtown area. Lastly, great outdoor area, we’d love to plan a trip there when warmer as well!

We had a great stay. The house is very big, spacious, well decorated and clean. It felt very cozy. The house rules were clear and the host was reachable at any time.

Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.

An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.

Great place. loved the pool table, darts and shall shuffleboard. lots of good wineries and cider places within 25 mins. pennings is our fav. didn't use the hot tub so couldn't comment but looked nice and private. driveway is steep but easily driveable. recommended. also didn't have coffee filters and they paid for some to be delivered same day! sweet.

I can't say enough about how lovely Melissa's home is. The home is so spacious, clean and beautifully decorated. We needed a local place to stay unexpectedly and were able to do a same day booking at Melissa's. We're so thankful we found her place because it met every need we had. Unfortunately it was pretty cold and ended up snowing so we didn't get to enjoy the patio and pool area but hope to be able to come back sometime to do just that. I'd highly recommend Melissa and her home whenever you're heading to Saratoga. It was a wonderful experience all around. Thank you Melissa!

A beautiful,peaceful spot and a comfortable home. We enjoyed lounging in the living room with the fireplace the most!

A beautiful and thoughtfully reconstructed house. It has everything you could need to enjoy a very chill time at the house indoors and outdoors or even cook a meal in. Kid friendly.Beautiful light. Beautiful views. Very convenient location. Kind hosts. We have stayed at a few places around town but this was by far our favorite house.

Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.

A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

We had an incredible weekend at Vanda’s home. It was even more spacious and beautiful than the photos and very comfortably accommodated our group of 13. We all fit at the long dining table and there were plenty of beds. The upstairs living room was our main hangout spot, it was cozy (multiple stoves in the house and a beautiful fireplace) and the view through the windows was stunning. And it was very warm despite the cold weather outside! The kitchen had everything you’d need as well. We didn’t have to go anywhere! I would definitely emphasize cars with 4wd for winter visits, the driveway was steep and the snow/freezing rain we got made it difficult even with 4wd. Our hosts kindly sent someone to plow for us, recommended someone to help us tow a car out that got stuck at the bottom of the driveway, and were very flexible and responsive. Be prepared for winter conditions but it’s worth the trip! Overall our stay was really awesome, I’d highly recommend this house for large groups.

What a beautiful place to spend Christmas!! Before moving to Australia next year we wanted one more cold snowy holiday. While we didn’t have as much snow as we’d hoped, it was still an amazing stay. The house is so homey and comfortable. With two young neurodivergent kids it’s hard being in a new place and the kids room was absolutely essential to our time there. The mattress in the primary bedroom is heavenly, and the overall decor and vibe of the house were incredible with enough room for everyone to have their own space (MIL included!). The kitchen was perfectly stocked and felt like we were right at home. We made a day trip out to Hunter Mountain to go tubing and a trip down to Kingston to Aldi and Target as well. Noah and Brandon were absolutely amazing hosts, Noah was extremely responsive even before we booked, and made sure we had what we need as our trip got closer. I would absolutely make the trip again and am so thankful for the memories we made!

We stay at Patti's place twice a year for a time of reflection. The location is peaceful and restful, right on the water. Patti always has a plate of cookies waiting for us and lets us know about any changes. We had a cold, wet first day, so were particularly delighted to be able to use the new gas fireplace, which kept everything warm and cozy. We're booked in for late fall already!

This Airbnb was spectacular just as advertised! Nice quick walk to the beach and beautiful scenery all around. Definitely recommend booking Airbnb with Charlotte because you’ll get the fantastic experiences.

This was our second time to stay. It had a gorgeous view surrounded by beautiful trees. It was so peaceful and relaxing with everything we needed. James is so easy to work with and very responsive. Highly recommended!

We had an amazing time here! Our family and friends spent the weekend for our son’s birthday and we felt right at home. The house is so cozy and comfortable. Will most definitely stay here again!

Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.

Seth’s place is great! We had a wonderful time in the hot tub and the kitchen was very easy to use. The bathrooms are fantastic! The property is beautiful and we fully intend to book again.

Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!

Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!

Absolutely gorgeous! Co-workers and family stayed together with plenty of space!

When I first pulled up to Kliment's, I literally teared up - that's how breath-taking his spot is. It was just what the doctor ordered... if doctors actually treated your mind, body, and soul and not just your body :) Seriously though, Kliment's place was an oasis for me: private, quiet, peaceful, with amazing views of the Catskill mountains. His home itself was beautifully decorated, simple yet super cozy, and had everything I needed and then some. (And the chickens were lovely company as well!) Kliment is one of the best Airbnb hosts I have ever had, hands down. With a very hectic schedule, Kliment was flexible, responsive, kind and patient with accommodating my many change requests and needs throughout my stay. Kliment is not just a wonderful host, but also a truly wonderful person - the world needs more people like him. In short: I can't recommend Kliment's home or him as a host enough! If you are hovering over the "Reserve Now" button, book it!!! You won't regret it! :)

Paula's house is epic. It is beautiful, large and perfectly equipped for a large group. Plenty of bedrooms to accommodate everyone with very comfortable beds, amazing large kitchen with two ovens, beautiful dining table and very large living room. Spent a weekend celebrating a birthday with friends and we never left! Not to mention the hot tub....