Guest house holiday rentals in Western Massachusetts

An incredibly charming, rustic, simple and comfortable small cottage, in a gorgeous rural setting. Just as advertised. It was perfect. Right across the road is Tivoli Bays, with beautiful trails for walking and hiking, and a small waterfall too. If you like, it's just a short walk to Broadway, the main strip in the village of Tivoli. You'll find a few restaurant options, a small market, sandwich shop, excellent coffee, and homemade ice cream. I met Yuko who couldn't be nicer and was a pleasure to chat with. A great experience all around - highly recommend booking a stay!

I was looking for a quiet place to stay a couple of days and Judy and Bob's place was the perfect place. Located in a very quiet neighborhood and near the town beach, it's a great to relax. Judy and Bob were very friendly and made me feel at home.

We were in Lenox to attend a reunion for the Lenox School for Boys ( Grad “66” ). The cabin was perfect for our needs especially because we could have our dog with us. Most of our time was spent with activities scheduled for the reunion so we didn’t really get to enjoy the peaceful atmosphere surrounding the cabin. There will be another reunion in 2026 so we will be looking forward to another stay at the Luv Shack. Thanks for sharing your abode. Pete & Becky Davis Mechanicsburg PA

A cozy spot that comfortably houses three adults, it's right on the river so it's perfect for fishing. While it feels remote, there are amenities close by like restaurants and grocery stores. And Bruce was a fantastic host, very friendly and helpful. I have no doubt we'll return.

This is a wonderful place to stay. It’s very clean and the hosts have prepared for everything. It feels like your own cabin in the woods. Plus there are so many activities in a short distance of the place.

Absolutely lovely space. So quiet, very secluded, extremely peaceful. I loved the outdoor shower, and the wind blowing through the trees at night was just lovely. The hosts were so kind and communicative - gave me a very warm welcome but then gave me the space I wanted for the rest of my stay. If you’re looking for a rustic stay in a tranquil place, I highly recommend!

A wonderful place in the country. A Berkshires hideaway. A close walk from the AirBnB is a great breakfast spot - The Store. tasty pastries, coffee and entrèes. It's the second Spring we have stayed there. We noticed that the bathroom was renovated from a tub to a walk-in shower. Good move! Weather this May was chilly and wet. We hiked Appalachian Trail anyway. One caution for seniors: the bedroom and bath are on the second floor up a narrow metal spiral starecase. Hard place to lug suitcases up the stairs. If you are seasoned backpackers, no problem.

By far the best Airbnb experience I've ever had! Joni was an amazing host, and I also had the pleasure of meeting her husband Rob/seeing their unique, beautiful home. She was responsive and very helpful throughout my stay, and even taught this "non tech savvy" person how to operate the TV! The location is perfect- and in my case even more so, as I attended a family wedding at the Colony just a block away! Its a 5 minute walk to town, and at the same time very peaceful/private- a perfect combination. I fell in love with Woodstock and wish I could have stayed longer. I'll definitely be back, as there is much more to explore in the area- will definitely stay at Logstock when I return!

The Nest was a great spot for us to rest and recoup before our NEYC day! Mary was easy to work with, communicated well, and provided a great space with so many thoughtful extras!

The house is very comfortable and feels like home. The kitchen is spacious and well-equipped — a great experience for cooking. There’s a peaceful courtyard that’s perfect for calming your mind or reading a book. One night, we even spotted a bear from the window! It’s a great location, and don’t worry — the bears are vegetarian. Elisa and Mickey are very kind and responsive. They’ll even create a personalized list to help you explore the town, even if you’re not familiar with the area. You can shop at Taft Farm — my favorite local farm. Cooking at the house really made it feel like home, and also “farm to table” experience. Thank you!

Beautiful, cozy accommodations. Comfy bed. Upscaled shower products. Wonderful towels. My husband said great coffee! The pool was inviting, but the weather was not cooperative while we were there. The actual space in the room is on the smaller side, but cozy enough for us two and our cockapoo. It was ultra convenient to our daughter’s house only 10 minutes away. We were there for family time but great recommendations for the area were given.

We absolutely loved our stay!!! The trail behind the apartment is awesome, and we loved the sound of the brook. We had a turtle friend too! We hope to return!!

We were day hiking the AT in the Kent to Cornwall area and stayed 3 nights at the Lodge. The lodge was comfortable, roomy and equipped with everything we needed. Brooke was great to talk with and very responsive to our requests and questions. My only regret is that we did not have enough time to explore the grounds of the estate which appear to be amazing and have a very interesting history. Highly recommended

This space is a separate addition to a home just off Cole Ave. plenty of room for two people. VERY comfortable bed. Easy walk to campus: 5-6 minutes to Dodd, 20 min across to Williamstown Theatre stage. Highly recommend!

The tiny horse was adorable and comfortable and the area was beautiful and peaceful. We loved using the outdoor shower

The in laws apartment felt like a cabin in the woods. Lots of privacy, clean stylish decor, the sound doesn’t travel in the brick house so it didn’t feel like we were in someone’s house. We used the backyard, hand an amazing bonfire. Were able to burn wood all night long and felt like we had the backyard to ourselves. The fireplace inside was another plus as it was a chilly June night. The place was equipped in everything you need. The bed was super comfy, and the energy of the place was extremely relaxing positive and natural. No force fake kindness to artificial superficial interactions with the host, which was something that we value when we traveled to Airbnb. They truly respected our privacy and made this last-minute the gateway, an unforgettable experience for my sister and I.. We will be back for sure :)

We needed a quiet place to stay with our 3 dogs while attending a wedding and visiting some of our grown children. The carriage house was perfect! Poppy let us check in a little early so we could change and get ready for the wedding. Our dogs felt right at home, and we felt so comfortable with the place and the neighborhood. Thank you Poppy!

My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.

The Eco Cottage was a perfect, tiny gem tucked away in the middle of the beautiful green woods. It was so private, peaceful, and serene. It truly felt like my own little retreat and since I was there to go on a retreat, this was the perfect place to lay my head at night. I loved walking the trails and wow, the pool, which looked so inviting (even if it was a bit too chilly to use this time!). Everything was clean, and the instructions were clear and easy to follow. Hosts checked in regularly but gave me my privacy. I really enjoyed my stay SO MUCH and will absolutely be booking here again the next time I’m in the area. Highly recommend!

Lovely place to stay for a wedding weekend. Would definitely return if in the area.

We stayed with family for a few days at Sarah & Chris' place, including a large dog and a kid in our party of 6. We felt right at home! Sarah and Chris were very responsive and gave great recommendations for local spots.

With a few dozen AirBnB stays under my belt, I have to say Shannon's lovely home in Ulster Park, NY, is without a doubt, the most enjoyable I've ever had! Her home is immaculate and literally footsteps from the Hudson River! She has taken the time to create an immensely enjoyable retreat by providing all modern amenities (large screen smart TV, robust WiFi and a fully equipped modern kitchen. Her backyard is thoughtfully laid out, recognizing the River is the main attraction, and provides fabulous seating areas, accompanied by gas fueled fire pits! Truly amazing. I am sure I will be returning soon!

Very lovely place. Close to town and ice cream shop. The hosts didn't bother you. Very soft bed. All in all we enjoyed our stay. We stayed for 11 days.

From making the reservation to checkout Jason was very communicative. Check in was easy, place was spotless and it had everything you would need for an extended stay. Our stay was from Sunday to Friday. Very peaceful and great place to work from. Beds were comfy. Restaurants and local grocery stores were all within a 10-15 minute drive. Everything was very accessible. Would definitely stay again if we were in need for a place in the area. Highly recommend.