
Holiday rentals with a kayak in Litchfield County
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Top-rated rentals with kayak in Litchfield County
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House rentals with a kayak

OWL's PERCH Candlewood Lakefront Rustic Cottage!
The Perch is perfect for a cozy getaway. Really feels like a home away from home. You can easily spend your days just enjoying the perch and all it has to offer, as well as go out and explore all the great surrounding areas! Walking around downtown New Milford and lounging by the lake were big highlights of our stay. We never had a dull moment! Casey is such a great host, always communicative and helpful. Her guides have everything you need to know and even have great recommendations for things in the nearby areas. We loved our stay!

Charming waterfront oasis on Candlewood Lake
We had a wonderful long weekend break from the city. The home was easy to get to, and while it was close to restaurants, shops, parks, and orchards, it was also very peaceful and private, tucked away in a private community. The home has three levels and rooms are well distributed and thoughtfully decorated. The kitchen had everything we needed (including Keurig and standard coffeemaker). Outdoor grounds and lake are beautiful. Our hosts were friendly and helpful and we are thankful for their hospitality.

Greystone at Twin Lakes
Thank you, John and Jen, for sharing your historical home with our family. The house is even cuter than the pictures, and we loved being able to walk right down to the lake. We had a great time exploring the lake with the canoe, and having a few chill nights inside, cooking and relaxing.

Waterfront house with scenic view of the lake
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!

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature
We started at David’s place for a bachelorette party and had an amazing time! The view over the lake is unreal and there was plenty of space for eight of us total. The driveway is a little bit tricky to get in and out of, but we had no issues at all – just flagging for those with larger cars and/or coming in bad weather.

Historic Country Retreat in Litchfield County
My family absolutely loved our stay! The home has been beautifully restored and is comfortable and clean. It was the perfect quiet getaway we were hoping for, while being close to all conveniences such as grocery stores, restaurants and coffee shops.

NEW! Charming Lakefront House
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.

Charming farmhouse retreat with post-hike hot-tub
This is our second time renting this house and working with Anna and Victoria. They are wonderful and kind hosts and so easy to work with. The entire home was very clean and spotless. We ABSOLUTELY loved our stay and had the perfect girls weekend. The farmhouse is so unique, vintage and spacious. The bathrooms are a women’s dream with the fun designs, lighting and the fun floor tiles. Although we are from Connecticut, we love visiting the Goshen/Litchfield area to get a change of scenery, visit the local winery’s and vineyards in the area and check out downtown Litchfield for lovely dinners and cocktail hours. The book case collection also intrigued us every morning when we were sipping our coffee and looking out the back porch area. We enjoyed the fact that there were tons of board games which we played at least one every night during our stay. We will definitely be booking our next visit and be back to this gorgeous home!
Cottage rentals with a kayak

Waterfront Cottage at Highland Lake w/dock
The cottage perfectly fit my needs for a stay in Winsted.

Longview Lakehouse - 5 min walk to private beach
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.

Lake Cottage in Goshen, CT
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. 🥰

Lakefront Cabin w/Dock & Beach on Candlewood Lake
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!

Candlewood Cottage
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!

Lake Waramug Cottage Washington CT- Ski Mohawk
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!

1 Bed Pond Cottage w/ Pool/Hot tub/Sauna access
The home was spotless and the view was even better than the photos. The living room has tons of windows and great fireplace.
Cabin rentals with a kayak

Lakefront cabin with private dock on stunning cove
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!

Waterfront Cabin: Love Lake Life
Great little cottage. Micheal is a great host. Since we live out of state and have relatives in Ct we would definitely go back. Great find

West Hill Cabin
Great location near West Hill Lake and Brodie Park; walking distance to public beach, playground, and more. The house is very clean and well provisioned. A great stay!

Lakeside Bungalow
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.

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
The perfect place to relax and disconnect! I’m going to miss falling asleep to the noise coming from the creek.

Cozy Cabin w/ Fireplace | On Lake
A few of us stayed at Mariana's for a girl's weekend to go to local events- and had a wonderful stay! The apartment was really aesthetic and perfect for a girl's trip, and we loved cooking in the kitchen as she had every appliance we needed, and loved the fireplace. Everything was cozy, well described, and had everything we could have needed! Mariana was friendly and helpful leading up to and during our stay. We'd recommend this for anyone wanting a cozy getaway!

Candlewood Cabin - with Private Waterfront
Our stay was everything we were hoping for! The cabin was spotless, beautiful (exactly as pictured), and so cozy! The views were gorgeous. Scott was incredibly responsive and helpful. It was an amazing weekend, we will definitely be back!

Cozy rustic cabin with beach on pond with 7 acres!
We really enjoyed our stay at the cabin. Our pets loved taking long naps by the fireplace. - clean place - responsive host - private and peaceful
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- Fairfield Beach
- Yale University
- Catamount Mountain Ski Resort
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Seaside Beach
- Woodmont Beach
- Taconic State Park
- Jennings Beach
- Thunder Ridge Ski Area
- Marvin Beach
- Walkway Over the Hudson State Historic Park
- Bushnell Park
- Calf Pasture Beach
- Wildemere Beach
- Bayview Beach
- Anchor Beach
- Mohawk Mountain Ski Area
- Sherwood Island State Park
- The Connecticut Golf Club
- Sasco Hill Beach
- Fort Trumbull Beach
- Point Beach