Vacation rentals with a kayak in Litchfield County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Litchfield County

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Guest favorite

Home in Brookfield

4.98 out of 5 average rating, 136 reviews

Stay at Old Dorset Farm & create lifelong memories

This 1905 Historic Old Bakery is the perfect location to create lifelong memories while exploring quaint New England. Set on 4 acres, with a lake, trails and golden rolling hills just minutes away, you’ll enjoy all of New England's beauty. Hiking, kayaking, antiques shopping or gallery visiting... it can all be done right here. But you don't have to go anywhere. The two fireplaces invite you to just stay, relax and enjoy the complimentary bottle of Prosecco. Follow us on Insta: @Old_Dorset_Farm

Guest favorite

Home in Harwinton

4.96 out of 5 average rating, 70 reviews

Direct Waterfront with Private Beach - Entire Home

Rare opportunity to enjoy DIRECT WATERFRONT living, great for your next vacation, relaxing weekend, or to work remotely. Fully furnished and completely remodeled home includes all amenities, complete kitchen and accessories, washer/dryer, central air, large deck, fast WiFi, Smart TVs. Featuring beach, swimming, kayaking, canoeing, paddle boarding, biking, skating and fishing. Enjoy spectacular views of the lake from the open concept home We are a SUPERHOST - Nearly 90% booked, so book early

Guest favorite

Cabin in Morris

4.94 out of 5 average rating, 18 reviews

Lakeside Bungalow

The Lakeside Bungalow is a 3 bedroom, 1 bath home, set in a private island on Bantam Lake. Built in the 1950’s this home was thoughtfully renovated in 2021, keeping the original lakeside charm intact. Go for a walk around the beautiful island, take a dip in the lake, play game of pickle ball, and top off your evening by building a fire (inside or out) and enjoying the peace and quiet. Under 2 hours drive from NYC, plan your long weekend getaway, explore the lovely Connecticut countryside.

Guest favorite

Home in Morris

4.86 out of 5 average rating, 148 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

Guest favorite

Guest suite in Sherman

4.97 out of 5 average rating, 156 reviews

Cozy Scenic New England country retreat w/ hiking

Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey or bike (2 bikes provided) along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian trail & other great hiking. Pets welcome. Inquire about min stay requirements.

Guest favorite

Cabin in Bethlehem

4.95 out of 5 average rating, 62 reviews

Cabin w/Fireplace | Perfect for Fall Foliage Views

Escape daily stress at Deer Ridge Cabin CT, a bright cozy retreat with all amenities. Relax by the fireplace or the private beach, paddleboarding, or kayaking at the lake, a 4-minute walk away. Explore nearby hiking trails and take in the stunning fall foliage, only 10 minutes from Litchfield for great restaurants & shopping. Close to local wineries. 2 hours from NYC, this peaceful cabin offers the perfect fall escape to nature while being close to everything! Your cozy getaway awaits!

Guest favorite

Cottage in Bethlehem

4.99 out of 5 average rating, 82 reviews

Minutes from March Farms | Hot Tub | Pet Friendly

The Cottage at The Grove is the perfect place to escape, the fall foliage surrounds the cabin and provides a peaceful setting. The Cottage features a wood burning stove, hot tub & outdoor fire pit. It is well equipped with everything you will need for your stay from a fully stocked kitchen to bath salts for the deep soaking tub. Minutes to March Farms, a must for fall activities. For security we have two exterior cameras facing the door & driveway. Escape to Litchfield County!

Guest favorite

Cabin in New Milford

4.96 out of 5 average rating, 135 reviews

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Our Little Creek Cabin is a place to pause. The cabin is located next to a rushing creek, where you can soak in a wood fired hot tub while listening to the sounds of the water. We are minutes from Candlewood Lake & Squantz Pond, where you take take our kayaks out. There are many wineries, breweries, towns to explore, antique shops, ski mountains, and beautiful hiking trails. Here you can simply open the windows to listen to natures sound machine! Find us on IG @thelittlecabins

Guest favorite

Cottage in Harwinton

4.97 out of 5 average rating, 34 reviews

Newly renovated 2 bedroom cottage on the lake!

Come relax by the lake! Peaceful, rejuvenating, and lots of fun on one of the cleanest lakes in CT. No gas engines allowed on the water, which ensures a peaceful stay. The beach is just 30 seconds away. Enjoy water views from the front yard and chill out in the evening at the fire pit. The owner lives just down the road and you're invited to use his kayak and canoe. The cottage is newly renovated, with a completely updated bathroom. Lots of windows and great light. Come enjoy!

Guest favorite

Home in Winsted

4.99 out of 5 average rating, 110 reviews

Cheerful 2 Bedroom Home at Highland Lake

Welcome to the Uncorked Cottage, a fun and relaxing space for you and your family to retreat to. Comfort meets style in this updated home with a cozy remote gas fireplace, 55” smart TV and high speed WiFi. The kitchen is fully equipped cook up your favorite recipes. Located across the street from Highland lake and walking distance to Resha Beach. Just minutes from downtown where you’ll find restaurants and activities for all. Just a short drive to ski mountains.

Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 344 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, SUP, two inflatable two person kayaks, and two wooden boats are available for use.

Guest favorite

Guesthouse in Morris

4.95 out of 5 average rating, 43 reviews

Peaceful Year Round Lakehouse

Kick back and relax in this calm, stylish space. Bantam Lake Gem; private walk in beach with kayaks, fishing poles and floats. 2 story open floor plan. 2 bedrooms/1 bath. Large beautiful deck. Countless hiking trails. Town of Litchfield Connecticut, plenty of eateries, county fairs etc. Beautiful western exposure, picture perfect sunsets all year round Ice fishing 🎣 in the winter, nearby ski slopes ⛷, concert venues, breweries and shopping