Holiday rentals with breakfast in Western Massachusetts

Helen was super helpful providing clear instructions for checking in and out & communicating fast and efficiently! The place was clean and peaceful to stay at. Would definitely recommend to friends and family!

We wanted a unique stay not too far from home for a brief break in our lackluster winter routine. Ken's farm certainly filled the bill. The best description we can come up with for the house is that it is part antique store, part natural history museum, part collectibles emporium, part library, and part very cozy home! We have never stayed in such an interesting, spacious, comfortable, and well-stocked Airbnb before. Ken is a very personable host who gave us a tour of the home he obviously loves after first having helped us lug our belongings from the truck. He answered questions promptly, kept the walkways clear of snow and ice, gave us fresh eggs from his chickens for breakfast, and had started a welcoming fire in one of the two fireplaces just prior to our arrival. If you are looking for a quiet country setting with a few pleasant surprises, Kenneth's farm is the place to be!

I worked hard to feel like I was a good guest. Sarah told me I went above and beyond by the many cleaning tasks I undertook, triggered by my boyfriend getting cut by glass on his foot trying to fold towels. That does not take away from Sarah or the property as a whole, because I believe these were overlooked tasks by the cleaning crew and therefore maintenance staff were unaware of it. It was almost immaculate until I started realizing that it was not as as tip top as the standards of cleanliness at “Top down housekeeping”, who’s owner and staff are thorough, honest & flexible with pricing.

Christine went above and beyond in welcoming us to her place. The fridge was stocked and she gifted us with homemade treats at the beginning and in the middle of our stay. Her place is spacious, clean, and comfortable. We enjoyed adventuring on the walking paths behind the house and her guestbook offered wonderful tips for Brattleboro and the surrounding area. We had a wonderful time!

Kira’s place felt just like home - comfortable, clean, warm, and lovely. Kira was also very responsive and kind in all her communications with us. We would absolutely stay again, without a doubt!

Madeline is a true professional as a host. This was our third time returning to her place because it has been a great experience every time in all ways. She is responsive and clear about what she offers and what she expects. Strongly recommend her and her beautiful place with great views

We had a fantastic stay at Shannon’s lake house! From the start, Shannon’s communication was excellent, making check-in and getting settled a breeze. The house itself is full of charm and offers a stunning view of the lake. It was impeccably clean, and the beds were very comfortable — a perfect retreat for our family. We were visiting my son's school and chose this property because of its convenient location and the opportunity for him to fish — one of his favorite activities. Shannon went above and beyond by charging the boat battery, ensuring everything was ready when the weather improved. Thanks to her, my son was able to catch several fish, including his first trout and smallmouth bass — a memory he won’t forget! Shannon lives next door and strikes the perfect balance between being available if needed while giving you complete privacy to enjoy the property. We would absolutely recommend this place to others and look forward to booking again in the future.

Gorgeous place in a great, walkable location. Our room was very clean & comfortable. Breakfast was excellent. Our host filled us in on the history of the inn and what's going on in Lenox. Hope to stay again soon!

We had a wonderful stay in this peaceful airbnb. We loved the layout and the views of the forest. The king size bed was super comfortable and Brianna was accommodating of my husband's need for down-free bedding. The exposed beams from the original barn and the natural wood made the apartment warm and cozy, especially during a powerful rainstorm. Highly recommend visiting the tiny cemetery down the road!

Tim! Our stay was Beyond my expectations! Many many thanks, appreciation and affection. Be well~ Jen, Lucia and Jack

We have a wonderful stay at Diane’s. Whenever we travel to Athens to kayak the Hudson River, we stay at Diane’s. It’s clean, cozy and close to all. Diane, thanks for a lovely stay. Mary and Rob

We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.

Susan's place is exactly as advertised and more. Very comfortable and well-equipped space with nice extras - coffee, tea, snacks, firewood and a grill with grill spatula, etc. Quiet, country setting that is a great value compared to hotels in the area. Would recommend and stay again.

Great hosts that make you feel right at home. We were greeted with some extra special touches that we were not expecting during our stay, that was very thoughtful. The space is exactly as pictured and very comfortable. We would definitely come back

Very lovely place located in a nice part of town. Mary and Lance were very welcoming and nice. We had a great stay and I strongly recommend this place for staying in Brattleboro.

The Modena House was perfect for our trip. We wished we had the chance to enjoy the outdoor aspect a little more, however time and weather didn’t cooperate with us. The place is adorable, a great kitchen, nicely decorated sitting room, bathroom and bedroom made for a lovely stay. The hosts are top notch! We hope to stay again in the future if we are in the area. Xoxo

Yet another wonderful 5-star stay at Jane & Karl's lovely home in Deerfield. Delicious homemade breakfasts, spacious and clean rooms, and always a warm welcome from Jane & Karl. Have stayed over 10 times across 3 years, and every time has been great - and there's always an improvement each time!

I am so honored to have been one of the last guests who had the privilege of staying in this beautiful home. Thank you, Chris and Fran, for the wonderful conversation, the magic tricks, delicious local breakfasts, recommendations, and opening your charming historic home to our travels!

Susan was a wonderful host! Even if I was out and about the whole weekend, she made herself available when I had questions, provided suggestions for cities to visit around North Chatham. The house is beautiful and peaceful, a heaven for birdwatchers and nature lovers!

We were all staying at High Grass Farm so we could attend the Brimfield flea market and the location of this place was perfect! The house itself was very nice and cozy. When we arrived, there were fruits, granola bars, and even a cake made for us to enjoy. The host, Karen, was quick to respond to our messages and even helped us out with our dog while we were out. Overall, an amazing stay and we hope to be back again!

We had a great time staying at the Lacey Rose! I appreciated the direction communication from Denise and being in a space that was so thoughtfully decorated and cared for. Breakfast made for us at the time we requested was a huge bonus as well!

Felt like we were nestled in the range of Mount Toby. The property and studio were super quiet, super non scented and clean with plentiful views to awe at. We needed ths peaceful trip while watching our son graduate. We are huge fans of Pioneer Valley. We know this area well so we took advantage of all great foodie places and all nature locations we could pack in. We would love to visit your place again! A slice of heaven for us

I was thrilled with my stay at this beautiful Airbnb, it met and exceeded all my expectations. The place was clean, quiet, private, and equipped with everything I needed to be perfectly comfortable. I would definitely stay again, and highly recommend to anyone who needs a place to stay!

Our stay was perfect! We both felt super comfortable. The bed and the room were clean and comfortable. Our host are gracious and friendly. We would stay again 🤩