Holiday Homes 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.

Great place, close to shops and restaurants. Very spacious, comfortable and quiet place.

The place was really wonderful we especially loved the sunroom.

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

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!

We absolutely loved our stay! It was so close to town, but very peaceful and quiet at night. The home had everything we could need, and was a perfect spot to relax in between exploring Hudson. Highly recommended!

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.

The photograph’s don’t do Joseph’s house justice. We had the pleasure of spending a family Christmas there, and it felt like a real home from home! The house was impeccably clean, warm and welcoming. It’s ideally placed for spending time at West Mountain and within easy reach of Lake George. Joseph’s communication is great. We can’t wait to return.

We were looking for a place to host thanksgiving dinner for 7 near my in-laws. Sandra's home near Lake Saratoga worked perfectly. Very large, open concept and huge kitchen with long dining table was exactly what we needed. With 4 bedrooms and 3 baths, it meant staying there was easy with space for us all. The on.y challenge for us was the steep driveway as we got hit with snow and rain. I would highly recommend this Airbnb.

We enjoy the stylish house and decorations within. The house is filled with cooking supplies, which helped a lot because we cooked two dinners there with our parents comfortably live six. We stay there during the winter month, but would love to return during the summer to enjoy the creek behind the house.

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

Some essentials in place such as toiletries coffee salt etc Home was comfortable and suitable to meet our needs Would definitely return

The place was immaculate and very well appointed with a lot of nice thoughtful touches. Super cozy but with high tech everywhere. Heated bathroom floor? heated towel rack. Lights were on remotes and dimmers. Really nice appliances and awesome coffee machine! they even had a pretty sweet acoustic guitar available for us to play. I got to meet Rich and Nicky and they were super sweet people and we chatted for a bit and they gave us tons of recommendations for spots to eat and things to do. I will absolutely plan to stay here again next time I'm in Dover for snowboarding. My wife and I come up a fair bit during the winter. Loved everything about this place!

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.

This was a fantastic home base for our family of four during our Berkshires vacation. We have a toddler and an infant, and had plenty of room to set up a pack and play in one bedroom and a bassinet in the other. The living room and eating area provided ample space to relax and play. The kitchen was very well stocked - we didn't do much cooking while there, but certainly could have hosted a nice meal. The space has a ton of comfortable seating, a lovely porch, and a beautiful view of the lake. Overall, very spacious, comfortable, and toddler-approved.

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!