Holiday rentals with a kayak in Litchfield County

Spent a cozy winter weekend in K.C’s cabin. K.C. made checking in a breeze. Throughout our stay, not only was K.C. easily accessible, but also very accommodating. Though small in size, the cabin had everything we needed. Would recommend to anyone looking for a cozy/antique vibe.

Greystone is a beautiful and very special space. The history of the home and family is fascinating! The space is comfortable and unique and the hosts are outstanding! The communication from start to finish was clear, prompt and so helpful. We were there for Thanksgiving and a couple days before we checked in, John emailed to ask we needed any special spices, pots or pans to prepare the Thanksgiving meal. Thoughtful touches like snacks, basic condiments (COFFEE!) and flowers greeted us upon arrival. We would love to rebook!

We chose this location for a peaceful family Thanksgiving weekend & we got exactly what we wanted. The home was quaint and clean. The lake was just beautiful. I loved having my morning coffee sitting on the couch overlooking the peaceful, quiet lake. My son brought his waders and ventured into the water to explore. We made s’mores at the outdoor fire pit & loved just hanging around the fire for family time. The neighborhood was so quiet, it felt like we were all alone! We Disconnected and enjoyed nature! It was just wonderful!

Beautiful place, very clean, gorgeous location and exactly what we needed/were expecting. Host was very accommodating, responsive, and helpful. Definitely recommend and we would love to go back again.

Absolutely perfect stay! This cozy, historic home in Woodbury is a true hidden gem. Tucked away on a peaceful, quiet road, it offered a serene escape surrounded by nature. We loved waking up to views of wildlife and the sounds of nature—it felt like our own little private retreat. The owners were warm, welcoming, and ensured we had everything we needed for a comfortable stay. The charm of the home and its historic touches made it even more special. Highly recommend for anyone seeking tranquility and a memorable stay. Five stars!

This is a very nice property right on the water. Very clean, comfortable, and tastefully decorated. Amenities and sports equipment are as described in the listing. Highly recommended. Very responsive host. We would happily stay again when in the area.

This Airbnb was truly better than the pictures. This lake house has its own private beach, is close to amazing eateries in Bantam and the house itself is modern and clean on the inside and is an amazing space to spend time. The deck and chairs as well as the fire pit and chairs on the beach make it all an amazing place to relax. Would stay again!!

Very responsive host. The house was exactly as described and pictured. Easy to understand instructions for check in and check out.

Great little place right on Highland Lake In Winsted, CT…. My wife was out of town we had a warm weekend in October booked literally day before brought the Jetski and 3 kids we had a blast, a little hard to find but good instructions, friendly neighbors, super clean, right on the lake would definitely go back. Also super responsive to questions and recommendations, other good thing is you can be in downtown Winsted in like 3 minutes for pizza or restaurants kids also loved Dairy Queen close by. Thank you again would definitely go back!!

Christienne was very responsive and helpful, the house was just as described and the location was so peaceful and quiet. Unfortunately I had to shorten my stay but I would absolutely be back if the opportunity presents itself.

Stayed at Adam and Nicole’s place for two nights while attending a festival nearby. Was a good size for myself, my daughter and a friend. The place itself is adorable and comfortable. Like staying in the three bears house in the woods with wifi, and gorgeous private wooded backyard and view to the lake across the road. The upstairs was a little stagnant upon arrival, but we opened the windows and put the fans on, which made it much better for sleeping at night. The house book and notes were very helpful. Kitchen and bathroom clean and well stocked! Loved it! Best of all, the hosts were accommodating and communicative. 🥰

My stay at the cottage was nothing short of beautiful and peaceful. Surrounded by nature, I felt completely disconnected from the chaos of everyday life, allowing me to truly unwind. The quiet mornings, fresh air, and cozy atmosphere made it the perfect retreat. The deep soaking tub was a wonderful touch—letting the warm water melt away all stress was exactly what I needed. I left feeling refreshed, reset, and ready to take on whatever comes next.

We enjoyed the stay on the lake. Having two canoes and two paddleboards was great for all kids to enjoy at the same time. The floating mat was a lot of fun. The house is located on a quiet off-shoot of the lake where no loud boats or jetskis can go at high speed so that instead attracted local ducks and fish, which was fun to observe. the slope of the property is a bit steep but the stairs did their job of keeping everyone orderly and safe. The house had a nice warming gift for us, which was well appreciated. The availability of beach chairs and lots of towels was a nice touch. Make sure to explore a local sandy beach nearby, we regret not checking it out from the start of our stay. The Candlewood Lake itself is huge and very peaceful with lots of water activities and other things to do nearby. Highly recommend to others!

Dana's house was absolutely beautiful and immaculate. It was an older house that had been totally redone with high quality amenities, furniture and appliances. There was everything you needed and most of it felt brand new! Dana was extremely responsive and provided a really nice welcome booklet with a lot of information about that area that was very helpful. This house was well worth the cost and I would for sure stay again!

My stay was everything I hoped for! The location to the lake was perfect and the views from the primary bedroom are perfect to wake up to in the morning! I was especially happy with the comfort of the bed, the linens and the pillows! I really enjoyed the fireplace. My stay was a very relaxing getaway, peaceful and rejuvenating!

We stayed here for 7 days with 2 small kids (2 and 4 years old) and wow was it amazing. The home is spacious and has everything we needed inside and outside the house. I could not have asked for anything else from the home and the dock was just so awesome to have, even caught 10+ fish right off the side. We rented a boat for a day from a marina and were able to come in and out of the backyard/house with no problems. I wish we could stay here for a whole month, but have to go back to real life!

lovely cabin, amazing location, hosts were fast to respond, especially qhen I booked an extra night

My family and I came back for a second year to stay at the West Hill Cabin because we loved it so much last year! Michael is so accommodating and extremely responsive. We can’t rave enough about the Great Room - that couch is so comfortable and my kids love the toy closet and protector! Looking forward to another stay next year.

What an idyllic cabin on the lake. Beautifully and thoughtfully appointed. Lots of activities right at hand, from games indoors to the pickleball court nearby. We had a wonderful experience.

What an awesome trip! The cabin and backyard was beautiful and we loved the hot tub. We recommend visiting Kent Falls and Craft Kitchen and Bar. Overall totally worth every penny and would love to visit again!

Mariana's cabin is the perfect cabin for a little getaway! She has thought of everything and so many awesome little details. She even had individual toothbrush and toothpaste in case you forgot yours! We cannot say enough about how great it is!!

Very nice Cabin. Amenities within the description were provided. Scott was a very helpful and assisted with any questions or concerns I had.

We really enjoyed our stay at the cabin. Our pets loved taking long naps by the fireplace. - clean place - responsive host - private and peaceful