Vacation home rentals in Western Massachusetts

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.

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.

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.

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!

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.

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

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.

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!

Jamie is a fantastic host! She is also kind-hearted and very hospitable. For example, Jamie asked me to let her know if I would be arriving after dark during check-in in order to leave the lights on for me and she checked in with me during this longer stay to see how everything was going, offering me recommendations for restaurants in the area or nearby hiking spots. If you get the opportunity to stay at her beautiful home I highly recommend it! Thank you Jamie!

The cabin was clean, cosy & comfortable and a good location to have my pets.

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!

Lovely place, exactly what my family needed

Great space, beautiful lake, host was friendly and responsive, no problem getting an uber to Athens and Hudson. Would absolutely stay here again.

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!

Entertainers paradise! Kitchen was fully stocked with platters, glasses, place settings, and specialty baking and cooking equipment. Just bring the food and nothing else is needed. Enough space for a kids and adult party on separate floors. Decorate well in minimalist style with all the modern conveniences. Even though there was a surprise snow storm on a holiday, was kept in the loop with plowing. They were very attentive. Thank you! Made many memories.

We were in the Berkshires for a family reunion and Randy's place was perfect for our group of 4 adults and 2 children. Randy suggested we arrive in the daylight as the streets are very dark which was great advice. He left the lights on for us and we were able to get in without any issues. Randy left notes all around the house explaining how everything worked and other helpful advice. The location is great and aside from the deer flies on my walk, everything was perfect. We even saw Yo-Yo Ma at the grocery store! We would definitely rent from Randy again!

Ivorlie’s home was everything my family needed. Set back in the woods, quite and easily found. We really enjoyed being able to sit in the living room being warmed up by the pellet stove. The yard was perfect for the kids to run around in and just be. Being able to walk down to see natural waterfalls or something that I really enjoyed. The house was pristine, and had everything we needed. Ivorlei was fast to respond to any questions we had. I would highly recommend this place to anyone looking to get away from the norm!