Vacation rentals in The Berkshires

We’ve stayed at Skip’s listings a few times, and it’s been wonderful each stay. Skip is helpful and quick to answer any questions. Andes is the most beautiful town. Highly recommend!

Well kept clean old house and furnishings. Terrific unobstructed view of the Hudson from two of the bedrooms and living room facing East. I loved sitting by the bay window in the master bedroom with the sun shining in watching barges on the river and with views of the town of Hudson on the far side of the river. The owners stuff was in the closets and refrigerator and freezer full of her food but that did not bother me. I appreciate having condiments, salt, sugar and pepper available. There is a washer/dryer but no dishwasher and only one bathroom. Also no shades on the East facing window in the master bedroom so light streamed in at sunrise.

Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.

This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.

Mary was a very nice, responsive and welcoming host . I would definitely stay at Halcott House again

Our family opted for a trip to New London to reconnect with our family for Thanksgiving. We were able to utilize the beautiful dining room for our dinner . We loved staying at Rosa’s place and were very comfortable . Just a note - there is only one bathroom and it is on the second floor ( as are all the bedrooms) We made this work but can be difficult with a larger family . It would definitely not deter me from booking again! This place was beautiful. The surrounding area and ease of access was comforting ! Would definitely stay here again .

Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.

Wonderful place for our family to spend the weekend while we attended our daughter's graduation a half hour away in MA. Clean, comfortable, spacious and charming in a quiet neighborhood. Auria provided clear instructions, check in was a breeze, and she was extremely proactive and helpful. She responded immediately to questions and was always cheerful and polite. One of the best Airbnb experiences we have had so far. I can not recommend this highly enough.

The Little Log Cabin was the perfect long weekend getaway. It was so comfortable and cozy. I would love to return the next time I’m in the Catskills. Thank you Becca and Jesse for sharing such a wonderful home!

Amazing little cabin! We will be coming back!

So beautiful! Had a great time just relaxing in the cabin. Very clean and comfortable. Brian and Stephanie were so kind and quick to respond. Will absolutely book again, especially in the summer!

Had an absolutely lovely stay at Billy's cabin! We only stayed one night but it was everything we could have hoped for. Being able to take the canoe out on the river was amazing. Even with the road on the other side of the river it was extremely peaceful. We ate out for every meal since town was so close and easy to get to. All we brought with us was some firewood, water, and an air mattress/blankets/pillows. Would definitely stay here again!!

The Creekside spot was a wonderful find! It's in such a convenient close location to town and the restaurants and shops, but also has a nice nature vibe. The cottage itself is lovely - solidly refurbished and comfortable as well as nicely designed. All appliances and amenities are new/well-kept, and organized. Bedrooms and beds are cozy and comfy. We had a rainy/snowy visit and it was lovely to watch the snow through the large windows. We would love to come back again and for a longer visit. Thank you so much for such a lovely spot!

I believe one of the best compliments to any AirBnB host is returning to their property: this was our fourth visit to the Clack Cabin, and surely not our last! We love the Clack Cabin for its coziness, comfort, and location. It's a small space, but has absolutely everything one needs. It's incredibly peaceful and relaxing, with the stream providing such a soothing soundtrack. The Clapper Hollow State Park a few steps away from the cabin has many easy and quiet paths to explore (we had the forest entirely to ourselves on Easter Sunday!). Clara is a wonderful host, very welcoming and helpful with local tips and knowledge. We already look forward to our next visit!

This cabin is such a cozy, serene spot with beautiful outdoor space. The stream and paths running along the property make it magical, and the pictures do not do it justice. In addition, the cabin had everything we needed and there are many things to do in the area. We look forward to returning and already booked our next trip!

Very comfortable and felt great to be inside this special little cabin. We brought our dogs and they were well accommodated here. The immediate road the house is on isn’t the best for walks but there’s lots of beautiful trails just a short drive a way. Although we were there during a very icy winter, I think the river behind the house would be fun to enjoy other seasons. Also great restaurants super close to the house.

John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!

We had a wonderful time at Mirav’s place in Woodstock. Made great use of the hot tub and the fireplace. We absolutely plan on returning soon!

Having a current child / Cadet at West Point and also another child / graduate of West Point , we always make it a point to stay at different Airbnbs in small towns around the USMA on both sides of the Hudson River . Melanie ‘s place was wonderful. Plenty of rooms/ beds for our Parent Weekend visit. Peaceful and safe location , yet a short 20 minute drive to the Academy . We felt right at home and look forward to staying at Melanie’s place again . The house was very clean and we had no issues at all !! Thank you

Family had a great stay at Danielle and Ben’s the house was very clean and kid friendly and we really enjoyed having the view of the creek from decking area. Very close to Mt Snow and surrounding area restaurants and attractions. Would stay again.

Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.

Excellent stay for a small group - we only stayed for a weekend, but would be a perfect spot for a weeklong trip as well.

I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.

We had a wonderful stay at Niall's! It was perfect for our needs. The house was clean and cozy. Niall was friendly and helpful!