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.

We had a great stay! The place was clean, spacious, and very peaceful. It’s in a great location- walkable and close to the main drag. We also really appreciated the thoughtful recommendations on things to do in the area. Overall, a wonderful experience and would recommend!

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

We really enjoyed our stay -- good vibes all around. Perfect location and the space kept going on and on -- really five rooms and an outdoor deck. The bed was a bit mushy but we slept fine. I'd 100% recommend this.

My husband and I had a wonderful stay at Cybele’s apartment. Super well located, stylish, incredibly comfortable, cosy and with wonderful small touches like candles, tea, coffee, lovely linen and stunning art work. It was exactly the cosy peaceful city getaway we needed, and our check in and check out could not have been made easier. Thank you, we will certainly come again!

We had a lovely stay in MA. We weren’t in the Airbnb much but the time that we did spend was quiet and peaceful. Blown away by the communication and responsiveness of the host. I left an earring behind and the host reached out to me a day after we checked out, and mailed it to me immediately. Super grateful for such a helpful host and a wonderful experience in the mountains!!

We had a wonderful time! The house was perfectly spacious for our big group. We loved the combination of open kitchen/living room/dining area where we could eat together while still having separate comfortable, quiet areas to spend time. Jean was wonderful to communicate with, and even returned something I forgot at the house. Would stay again!

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.

Our second stay in two years. This place doesn’t not disappoint. This is an amazing place. I hope to stay again next year. Love it here.

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.

Wonderful cozy house just 2 hours away from NY. Rachel and Lam were very responsive and attentive. Looking forward to going back 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!

My goal was to create a memorable Thanksgiving weekend for my family and friends and Anna’s place made it happen! This is a beautiful home, full of light with all the windows and gorgeous wood floors. The layout is ideal-5 bedroom suites with their own baths and TVs, a large living room, a bar/TV area and that amazing dining room with a 20 seat dining table. Everyone has their own space but also plenty of space to gather together. The kitchen is a commercial kitchen- great for baking and cooking for a crowd. There were plenty of plates, flatware, glassware, serving dishes too. I have several pictures of that large dining room full of smiling faces and delicious food! The bar area was a big hit-great for cocktails and watching football. We were blessed with beautiful weather and were able to take advantage of the spacious outside area too. There were a few minor things but overall it was wonderful and a very special memory for all of us. Highly recommend! Thank you Anna and Aaron!

Scott was a terrific host and his place was exactly as we expected. Large and spacious, very comfortable bed. We had a few rainy days and were stuck inside a bit more than we expected, but Scott’s place was warm and comfortable, and we didn’t feel crowded in. Would stay there again.

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!

The perfect stay for our trip to Tanglewood and Berkshire museum! I loved the space and how the place was furnished. Leaving some of the old charm and adding new retro pieces really tied the place together. Plenty of room for our group of 3 adults and two kids! Parking is a little tight for our trucks but there’s also plenty of street parking if necessary.

What a warm, peaceful, and wonderful place! We will be back!

We stayed a couple of days at Ty’s beautiful house as a base for skiing Mount Snow. It was a fantastic experience and Ty was very responsive when we had questions. It is possible to take the Moover (free shuttle bus) to Mount Snow right outside the house - it simply couldn’t be easier.

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!