Cottage vacation rentals in Pioneer Valley

Darcy is a top host. We loved the in-wall USB chargers and the bluetooth speaker, the welcoming wine, the beautiful layout and decor, the cozy feeling with lots of space for us to sprawl out and the high quality of the renovation. I felt secure and cozy and everything from the hot tub to the sheets were super clean and fresh. We will be back in the summer for kayaking on the lake. Thank you Darcy!

This house is gorgeous right on the lake in the winter was so beautiful. The home was clean and had everything you needed. Absolutely loved Catherine’s guidebook so well written and amazing communication. I would recommend this stay for anyone who loves a staycation!! Thank you for an amazing weekend! 💕

My girlfriend and I had a great time staying at Joktan’s place. We really enjoyed the home as well as the amenities that came with it. Joktan, provided excellent communication. Would recommend staying here!

The Cottage at Blackberry River Inn was beautiful and exactly what we needed for the weekend. Breakfast was included and wonderful. This place is a gem and we will be back for sure.

Our host was extremely helpful and pleasant to all our questions, and the accommodations were comfortable with all the amenities of a normal home, plus a very pleasant and private hot tub. Would stay here again.

Truly a magical spot--in October, the fall colors. Any time, the lake view, and the absolutely lovely sunroom.

This place was absolutely beautiful and perfect for our weekend away. The house was spotless, had everything we needed, and was the most cozy little cabin right on the water. We really enjoyed our stay, and would love to go back in the near future!!

Loved our stay! Very clean and quiet. Nice and private as well. They allow pets which is awesome. Would love to stay here again.

Another perfect stay at Laurie's. This is our third stay over Thanksgiving week and we always are sad to leave. My family absolutely loves staying here. There is plenty of room to gather or to have some alone time. Beds are comfortable. Kitchen has everything you could need and is always pristine. Check in is stress free. Area is peaceful and serene. Lee is a lovely New England town. Downtown is less than a 5 minute ride. Many restaurants within a 5-20 minute ride. Outlets are 10 minutes away. Looking forward to our stay next year.

I had an amazing stay at Bill's house in Readsboro! The house has been beautifully renovated and is incredibly spacious, with plenty of bedrooms to accommodate a large group comfortably. It was well-stocked with everything we needed to host, from kitchen essentials to an array of board games that kept everyone entertained. Bill was extremely responsive and friendly, even dropping by for a quick chat and to introduce himself, which was a nice personal touch. The highlight of the property was definitely the massive game room. It was packed with all sorts of fun activities, from shuffleboard and pool to karaoke—everyone had a blast singing their hearts out. Overall, the experience was a solid 10 out of 10, and I wouldn't hesitate to book again. Highly recommended for anyone looking for a spacious and fun place to stay!

This place was an excellent location for basing our trip to the Berkshires. We liked looking out over the lake, and walking around the community.

This was our second stay after the first a year ago. So we knew what to expect and were not disappointed. This sweet place and location are perfect for a Berkeshire vacation combining hiking with the amenities of Great Barrington.

This cute cottage’s was exactly what we were looking for. Our stay was short but Meredith gave us great suggestions for places to eat to help us avoid wasting our minimal time searching. On a fall weekend the neighborhood was quiet. It was a really nice weekend stay for us.

Had an amazing experience staying at Renee’s beautiful cottage. It’s quiet and tucked away but very accessible from the main roads. I highly recommend staying here if you want a cozy getaway with all the amenities you’d need for a comfortable and enjoyable stay. The fireplace was definitely the highlight of the cottage.

I can't compliment the host enough. 10/10 She was very responsive to messages. Host was flexible and very accommodating to additional requests. Also, a very beautiful place at excellent rates considering the various amenities. The Property was exactly what I needed to get unplugged from the hustle and bustle, commune with nature, do some reading and meditation. Only having TVs in the common area allows families to unplug and encourages shared activities

Gillian was a super host. The place was clean and ready for us when we arrived including a decorated Christmas tree, doggie dishes, and a full wood pile. She got back to us in a timely manner for all questions. And all expectations and facts about our stay were communicated in a clear way. Thank you Gillian!

Perfect spot for a peaceful, relaxing Berkshires weekend and/or visit to Tanglewood. Beautiful location of the cabin among the trees, super convenient to lots of hiking, cute towns to wander with great food, and town beach for swimming. And, couldn't be better situated for catching a show at Tanglewood. Sonia was also helpful, responsive, and friendly about all of the preparation details and made the logistics of the trip simple.

Very nice and cozy house during the winter!

I have stayed in this little house several times, and it always seems like the perfect place., not matter what the season. The yard and surroundings are lovely and the house itself is cozy and beautifully maintained. The host is always so responsive and helpful.

The Stone Schoolhouse was an awesome place to stay. The classroom was fascinating and very cool. Rich and Cheryl were very friendly and helpful. One downside was that the primary bedroom and the bathroom were on different levels, but everything else was so great that this seemed like a minor inconvenience and the overall experience of staying there was still great. We stayed at the schoolhouse in February during a deep freeze and found the heat to be sufficient and in general that it was a good place to be in the winter.

My husband and I had a wonderful stay. The cottage was clean and comfortable. The hosts thought of everything and made us feel right at home. We could not have been more pleased and would highly recommend this property.

Brenda place was beautiful with a beautiful view especially when we work up to some light snow on the lake. The layout of the house was ideal for us with the big open living room and great updated kitchen. So many comfortable beds for us to use. Our favorite places were the sun room and dining rooms looking out at the lake, Brenda was was kind and helpful and adding a Christmas tree for us was a beautiful touch . Highly recommend, one of our best for sure, thank you

Our stay at Hope House was EXACTLY what we needed! Andrew was a truly wonderful host - he was so helpful, responsive, and proactive. He anticipated that the steps would be icy one morning and had already been over to put down salt/sand. We really appreciated how thoughtful he is! The space itself is also so peaceful and serene, which is exactly what we were hoping for. We really felt at home and comfortable. The location was beautiful and we really loved Ashfield - it’s a small town, but has plenty to do and the people were very friendly and kind. We would absolutely recommend staying at the Hope House - a special space with a great host!

We had such a nice stay! It is in a great location and is just a couple minutes walk to downtown Williamstown. The kitchen was updated and everything was very comfortable! I would definitely stay here again.