Holiday rentals with a kayak in Windham County

Loved our stay here! The host was so helpful and helped us out with whatever we needed! Amazing place!

Whitley's place was just what we were looking for for our family weekend! Plenty of space with lots to do, the pool table was a big hit. Very close to Mount Snow and Stratton which was really convenient for the snowboarders/skiers in our group. Had a great time and would love to be back!

Our family of 11 had a great time at this beautiful home during the Thanksgiving holiday. The views of the pond were incredible, especially after it snowed, and the hosts were extremely responsive and accommodating. There was plenty of room for us all and we highly enjoyed our stay. Thank you Ritu and Darshan!

Great space! We were comfortable with a big group here, and loved being so close to the slopes. Hot tub seems new and is in great condition.

We stayed for a long weekend and our stay with Sarah was perfect! The cabin is even cuter than the photos and is very cozy. It was perfect for our ski weekend at Okemo (only 20ish minute drive!). Very quiet and peaceful. The horses and the pupper on the property were extra charming. When we arrived, there was popcorn and candy to welcome us and helpful information for our stay. The cabin is warm and inviting and has everything you might need. Everything about the space is clearly very well maintained, including the horses which are obviously well cared for and loved. We definitely plan to stay here again!

We had a great weekend at Lisa's house! Lisa was easy to get in touch with and when she knew she might be out of touch she gave us an alternate person to contact. It's snowed overnight during our stay and we were plowed out early to get on the mountain for first tracks. The house is exactly as pictured on the listing, we were very comfortable, and the hot tub was key for relaxing after a day on the mountain. The house has a 80's feel to it, and the wood panelling gives mountain vibes. We had everything we needed for our stay and really enjoyed the time we spent together!

Wendy’s house was great for our group of 12! It’s in a prime location, she was super responsive, and the house is big and comfortable.

We had a great time at this Airbnb! The game room was a selling point and it didn’t disappoint! The house was very spacious so everyone was able to have their own space if they wanted. The short walk to downtown was perfect and the town was so quaint and filled with friendly people! I would highly recommend this place we had an excellent time.

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!

Loved Ali’s cabin ! Small and cozy, has all you need. Ali was super responsive and clear. Would love to stay again.

Such a cute cottage! The cottage was clean and the beachfront was beautiful. Ali was very responsive and helpful. Great stay!

Ron & Priscilla are fabulous hosts! Extremely friendly and kind. They really went above and beyond to make sure we were safe and having a good time. They saved us from a winter snow storm AND a black out! They even came by to clear the snow on the path from the car to the house. The amount of things they did to make sure we were comfortable was really above and beyond. We felt right at home. The house was cozy and comfortable. The area is private, quiet and the surrounding area is beautiful. I would highly recommend anyone to stay with them. If we had more time off, we wouldn’t hesitate to go back! They really made our stay special.

The cabins were terrific. We had three cabins as a group. They are across the street from Spofford Lake, which has a small beach and a dock. We had a terrific night hanging out on the beach while lighting a fire in the pit. We had a great visit at Copper Cannon Distillery (located down the road) and went on a few hikes.

We had a lovely time at the Library cottage, sitting on the porch, walking the grounds. Nice to spend time right on the beach that has Adirondack chairs and a fire pit. Our host Ali was always available and helpful. The bunk bed layout was a surprise, but worked out fine. We’d love to come back, maybe even in the summer. Thank you Ali for a welcoming stay.

Karen and Robs little cottage was perfect for our month stay in Vermont. Secluded in the woods but also close enough to town and the ski mountains. We had a blast and Karen was incredibly attentive and responsive with any of our needs. 4WD definitely a necessity if you are coming in the winter/shoulder season months.

It was a quiet, peaceful stay! Loved the hot tub!

My friends and I really enjoyed this location -- great fireplace and pit outside, really quaint spot. We also really appreciated the small touches that the host added (already had fire wood ready, some basic spices in the cabinets, and even though we didn't need them, they had tampons and toiletries available in the bathrooms). Would recommend and stay again.

Stayed for a ski weekend at Mount Snow. Nice, clean comfortable place, and we enjoyed the wood stove after skiing. We would definitely recommend this location.

We love it here! This was our third stay, and it’s become our annual go-to to celebrate my husband’s birthday. Great walking trails, beautiful cottage, the perfect place to unwind!

We stayed here for four days in August, and it was a great place for us. As someone who frequents this area for camping, I booked this weekend needing a cabin instead to accommodate other guests that do not camp. Plenty of room for everyone. This cabin was so tranquil and the sound of the water fall/river was perfect. It was quaint and cozy. The kitchen was stocked with plenty of cooking utensils, pots, pans, etc. bathroom and bedrooms are clean. The front porch and deck provided excellent outdoor space. The owner was so wonderful - texting us safe travels both check in and check out days and clear instructions on coming and leaving the home. I will gladly stay here again and am looking forward to doing so!

We had a great visit and would definitely rebook. We loved this beautiful house in such a peaceful setting close enough for our day trip to Mt. Snow. The accomodations were perfect for our group of 10- 5 adults & 5 kids. Very nice bedrooms, and beds with plenty of bathrooms. The living room is spacious and open, containing a charming fireplace and wraparound deck with a gorgeous view. The bunkbed room was perfect and gave all the kids their own space. Cons- 10 am checkout - way too early! The back slider door is broken and difficult to keep on its track - safety issue. The hot tub was insanely hot and hard to regulate. Not even one ping pong ball at the house for the table so the kids couldn't even play. Such a small thing but such a big bummer! :(

We had a great stay at this Vermont cabin. It felt like home right away, and we quickly got comfortable in the cozy living area. We spent hours playing cards around the table, enjoying the fireplace. The showers were hot, and the kitchen was well-equipped, making cooking a breeze. We had a few questions which Eva responded to quickly. It was amazing that she was kind enough to offer a late checkout, too, so we could enjoy our last morning and breakfast together. All in all, it was a comfortable and relaxing stay.