Vacation home rentals in The Berkshires

We had a lovely stay at Chalet on a Hill and Nadine was lovely to work with. House is very private with great views and close drive to Windham where dinner was recommended. The grocery store nearby has everything you need if you want to make the house feel like home for the weekend. We will certainly look to book again.

The location is great, beautiful location. The hot tub was wonderful and the pool table was enjoyed by all.

Kelly was super responsive. The house was 5 minutes away from Okemo.

Excellent location, close to all the art galleries, cafes and restaurants Hudson has to offer. It is also a short drive to other points of interest like Olana, the Thomas Cole house and Catskill, NY.

The space was clean, cozy, and exactly as advertised! We had no trouble getting in, and Vladimir was very responsive and flexible about our check-in time. We were easily able to walk to the center of town and to the Amtrak station, and all of the best restaurants in Hudson are nearby.

Booked the place for a guest visiting. They loved the place. Was clean and spacious. Would rent again.

Amazing Time in this house. Pictures don't do justice because the place is great with beautiful views. Paul was accommodating and very helpful. This has been my favorite place.

The Okemo Oasis home was a fantastic place for our annual cousins’ ski trip. It had plenty of space for everyone to sleep, relax, and enjoy the open living, dining, and kitchen area. The many bathrooms was a big plus, and check-in was seamless. There were very few downsides—the beds weren’t the most comfortable but were manageable for a short stay, and the road access was a bit tricky, though that’s beyond the host’s control. While there was no cellular service, they had WiFi. Overall, it’s a great home, and we would definitely stay here again!

This house is the perfect home base for skiing at nearby Belleayre, which is only a few minutes away by car. We have spent several weekends there. It was clean, had lots of comfortable beds, and space for our ski gear. The kitchen is perfect for preparing simple meals after a day on the slopes. The hot tub is a great place to relax sore muscles. The surroundings are lovely. The host was always responsive if we needed anything. Overall it's a great place to relax in the Catskills however you like.

Cybele was super responsive and helpful when I had the tiniest issue getting into the apartment upon arrival that was quickly resolved. Location is great, less than a five minute walk from Warren Street where most of the shops/restaurants etc options are. Felt very secure and safe. Need to schedule Ubers from the train station if arriving/leaving late. Highly recommend Pilates Hudson if you want a local workout!

All the glowing reviews are true. The pics of Gamble’s lovely cottage don’t do it justice!! Its beautiful. Super clean. Lots of amenities. Main Street is just a block away! Everything you need to know is in the handbook. However, should you have any questions Gamble replies right away and is always happy to help. You’ll love it here.

Had a great stay! The place was clean, cozy, and exactly as described. The host was friendly, responsive, and provided great local tips. Highly recommend this place for a comfortable and enjoyable experience!

GREAT HOUSE, GREAT SERVICE.... HOPEFULLY WILL BE BACK

The home was absolutely stunning. Michelle was attentive and very accommodating. Definitely recommend this rental and host.

A true retreat spot- peaceful with lots to do. The home is a perfect Air BnB- lots of bedrooms, great hang out spaces, fun amenities (pool table, ping pong, hot tub, huge tv), awesome kitchen. The topper is the amazing river setting! One of the best spots I have stayed. Highly recommend!

Had an awesome stay, couldn’t ask for more!Quiet and remote just what we needed on our getaway. Will definitely return for future trips. Thanks Chandra!

Quiet neighborhood. House and property are welcoming and just as described. We had a snowstorm check-in day and Larry was responsive and made sure the snow and ice were cleared prior to our arrival. The kids and the dog enjoyed exploring the property despite the single digit temps and 20 inch base of snow. This property is close to so many awesome winter activities! We made the most of our 4 night/5 day stay and went cross country skiing at Canterbury Farm, snow tubing at Bousquet Mountain, and snowboarding at Otis Ridge. It was great to have a well appointed kitchen for home cooked meals, and a woodstove with plenty of firewood to beat the frigid temps. Overall - awesome!

A beautifully remodeled country home in an amazing location; with a view of Shwangunk Mountains and the Hudson valley, surrounded by large open fields, providing privacy and perfect for stargazing. The home is spacious, comfortable, tastefully furnished, perfect for a party of 6 to even 8 people. The kitchen has all the best equipments, tools. The "on demand" hot water system worked very well for us. Shane is a wonderful host, very responsive and helpful. There are amazing hiking trails close-by or one can just walk around the area and enjoy the outdoors right on the property. We very much hope to come back sometimes in the spring or summer time for some hiking and enjoying what this wonderful home provides with visitors.

The house is so well preserved yet the updates make it feel comfortable and modern. The fireplace was awesome to share with our family on a cold and rainy night. Being close to the waterfall/river was also lovely. We were there between seasons, and in the summer it must be divine.

Big thank you to Rich & Nicky, their place was gorgeous, spacious and comfortable for my parents, sister and our dogs. We felt right at home. They were very responsive and helpful throughout the weekend, a pleasure to communicate with. House was a 5 min drive to Carinthia, 9min drive to Wilmington. We took their recommendation and had my 40th birthday/easter brunch at the Sawmill just across the street, delicious. Went to the Alpenglow Bistro the night before for dinner, we couldn’t be more pleased with the dining options this stay. Was happy to have skied this late in April in southern, VT as well! Would highly recommend staying at the 1827 House when visiting Mount Snow and the surrounding area. High end features like the towel drying racks were an added bonus and the espresso machine was a hit! Will definitely be booking again!

This is our third time staying at Mark and Anne’s house and we are already looking forward to coming back! Mark and Anne are INCREDIBLY responsive and very helpful. This is the perfect place for a get to gather with friends or family. The house is stunning and has everything you need - perfectly private location as well! Thank you Mark & Anne!

A Dream Getaway by the Water! Our stay at this waterside rental was nothing short of perfection! From the moment we arrived, we were blown away by the stunning views, impeccable amenities, and the incredible hospitality of our host. Every detail was thoughtfully curated to ensure a comfortable and luxurious stay. One of the standout moments was the host’s remarkable responsiveness. When a power surge unexpectedly took out the coffee maker, we reached out, and literally within minutes, a brand-new, state-of-the-art coffee machine was delivered to our doorstep! It was clear that guest satisfaction is a top priority here. Whether you’re looking to relax by the water, enjoy the beautiful surroundings, or simply unwind in a home that offers every modern convenience, this rental is the perfect choice. We can’t wait to return!