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Vacation rentals with a kayak in Litchfield County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Litchfield County

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A bright bedroom features two twin beds with white wood frames, positioned on either side of a decorative fireplace. A round wicker table sits at the center, adorned with a vase of flowers. Light streams in through multiple windows, creating a warm ambiance.

Home in Brookfield

4.98 out of 5 average rating, 148 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

Top guest favorite

A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.

4.99 out of 5 average rating, 152 reviews

Luxe Bolton Lake

Past guests rave about the Luxe! Enjoy beautiful Middle Bolton Lake, and relax in the stylish comfort of our 3 bedroom/3 bathroom architecturally-designed home. The Luxe features an expansive direct waterfront, outdoor jacuzzi, gorgeous primary bedroom suite w/ private shower/tub, artistic furniture, cozy fireplace, coffee bar, complimentary snacks, WiFi, large deck, fire pit, kayaks, vintage aluminum canoe, board games, and much more. Come stay at the Luxe lake house and make lasting memories.

Top guest favorite

Home in Putnam Valley

4.99 out of 5 average rating, 104 reviews

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Top guest favorite

Cottage in Southwick

4.98 out of 5 average rating, 109 reviews

4 Kayaks Fire Pit & Lake Views from Hot Tub

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

A waterfront home with a unique tower design is reflected in the calm waters of Bantam Lake. The house features multiple outdoor decks, large windows, and is surrounded by trees, providing a serene setting. A private dock extends into the lake, inviting exploration.

4.86 out of 5 average rating, 151 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.

Top guest favorite

A wooden dock extends over calm waters, featuring a canoe and two stand-up paddleboards tied up. Lush trees line the opposite shore, reflecting in the water under a cloudy sky.

Cottage in South Salem

5 out of 5 average rating, 106 reviews

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

An outdoor fire pit is surrounded by several adirondack chairs on a grassy area. A stone wall frames the fire pit, with trees and a glimpse of a secondary building in the background. The scene reflects a serene natural setting.

Cottage in Bethlehem

4.98 out of 5 average rating, 104 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

A spacious living area features a large sectional sofa adorned with cushions, offering panoramic lake views through expansive windows. A dining table for two is located nearby, with a small workspace and desk chair positioned to enjoy the serene scenery.

Cottage in Plymouth

4.94 out of 5 average rating, 118 reviews

Lakefront Cozy Oasis 2BR w/ stunning sunset views

It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits!

An outdoor dining table is set beneath the trees, featuring a linen runner, plates, and glasses. Fresh oranges and a vibrant fern centerpiece add color, while the serene lake can be seen through the foliage in the background.

Cabin in Sherman

4.97 out of 5 average rating, 388 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, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

A warm wooden interior is highlighted by a charming dining area featuring a small table set for two. Natural light streams through double doors, revealing scenic views outside. Soft curtains adorn the windows, and a small kitchenette is visible in the background.

Guest suite in Sherman

4.96 out of 5 average rating, 171 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 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.

An inflatable kayak rests against the wooden cabin's exterior, showcasing a green and blue design. The porch features wooden railings and a hanging flower basket, while a window reveals soft curtains inside. Lush greenery surrounds the area, enhancing the cabin's natural setting.

Cabin in New Milford

4.95 out of 5 average rating, 171 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!

A serene lakeside view showcases a vibrant green lawn framed by mature trees. Colorful kayaks and a paddleboard rest beside the water. A picturesque scene is enhanced by blooming pink azaleas, with the calm lake visible in the background.

Cottage in Pawling

4.98 out of 5 average rating, 124 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

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Popular amenities for Litchfield County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in New Milford

4.96 out of 5 average rating, 91 reviews

The Getaway: Beautiful Waterfront - New Milford CT

A serene lake is surrounded by lush green hills, reflecting the clear blue sky. The water is calm, with a small rowboat visible in the distance, adding to the tranquil outdoor setting.

4.99 out of 5 average rating, 181 reviews

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

Top guest favorite

Home in Farmington

5 out of 5 average rating, 62 reviews

Lake Escape: Lake Cottage Charm, Lake Front, AC

Several colorful kayaks are lined up on a grassy area near a tranquil lake. A wooden dock extends into the water, surrounded by lush trees. A park bench offers a comfortable spot to relax and enjoy the serene natural setting.

4.94 out of 5 average rating, 149 reviews

Lake front retreat - Stylish Berkshire home

The interior space features a white armchair beside a decorative wooden stool and a black coffee table. A tall ladder leads to the lofted area, while a metal shelving unit displays a framed image of a cow and a plant. Exposed wooden beams complement the natural decor.

Home in Egremont

4.94 out of 5 average rating, 81 reviews

Modern and Stylish Country Lakeside Cottage

Home in Newtown

4.83 out of 5 average rating, 6 reviews

Serenity by Lakefront Cottage!

The exterior of a black, A-frame house is surrounded by lush greenery. A gravel path leads to the entrance, where a small seating area with blue chairs sits on a deck. Vibrant lilac blooms add a touch of color to the landscape.

Home in Tolland

4.95 out of 5 average rating, 60 reviews

Spacious Home w/ Hot Tub in Private Lake Community

A charming historic home is nestled among lush greenery, featuring a well-maintained lawn and stone landscaping. A wooden door adds a rustic detail to the white exterior. Flowering shrubs are visible, enhancing the natural surroundings, while a cozy seating area is positioned nearby.

Home in Woodbury

4.89 out of 5 average rating, 66 reviews

Historic Country Retreat in Litchfield County

Cottage rentals with a kayak

A dining area offers a wooden table surrounded by black chairs, with large windows overlooking the lake. Slate flooring complements the bright, airy space, creating a seamless connection to the outdoor views. Natural light fills the room, enhancing the serene ambiance.

Cottage in Putnam Valley

4.96 out of 5 average rating, 165 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

A vibrant sunset reflects off the water, casting golden hues across the sky. The landscape features rolling hills in the background and a serene lake bordered by trees and homes along the water's edge.

Cottage in Brookfield

4.92 out of 5 average rating, 36 reviews

Longview Lakehouse - 5 min walk to private beach

A charming two-story cottage is framed by lush green foliage, showcasing a light-colored exterior. Natural light filters through large windows, and a wooden deck extends at the front, inviting relaxation in the surrounding nature.

Cottage in Goshen

4.73 out of 5 average rating, 45 reviews

Lake Cottage in Goshen, CT

Top guest favorite

An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.

Cottage in Guilford

4.99 out of 5 average rating, 102 reviews

Waterfront Joshua Cove Cottage with private beach.

Top guest favorite

A sunlit porch area features a spacious bed adorned with a white quilt and colorful accent pillows. A striped rug lies on the floor, while wicker furniture and large windows create an airy atmosphere. Natural light fills the space, offering views of the outdoors.

Cottage in Guilford

4.94 out of 5 average rating, 268 reviews

The Cottage at Indian Cove

A backyard patio area is shown, featuring a seating arrangement of several chairs and a table. A fire pit is positioned on a stone surface, surrounded by grass and landscaping. The view overlooks the lake, with boats visible in the background and lush trees framing the scene.

Cottage in East Haddam

4.9 out of 5 average rating, 131 reviews

Direct Waterfront Cottage on Moodus Reservoir.

A serene wooded area is shown, featuring tall trees with lush green leaves. Sunlight filters through the foliage, casting gentle shadows on the forest floor. A glimpse of Candlewood Lake is visible in the background, enhancing the natural beauty of the surroundings.

Cottage in New Milford

4.97 out of 5 average rating, 69 reviews

Waterfront, Wooded Cottage on Candlewood Lake

Top guest favorite

The newly renovated house is set against a backdrop of trees, featuring a charming exterior with grey siding and a brick chimney. A small porch is visible, and colorful autumn leaves are scattered across the front yard, enhancing the welcoming appearance.

Cottage in Colchester

4.97 out of 5 average rating, 174 reviews

Lakefront peaceful getaway cottage

Cabin rentals with a kayak

A warm bedroom features a spacious bed covered with a light-colored bedspread. Two framed artworks, depicting serene outdoor scenes, adorn the walls. A window is dressed with a light-filtering shade, providing soft natural light, while a small bedside table with a lamp is positioned next to the bed.

4.8 out of 5 average rating, 20 reviews

Simple, rustic, cozy get away

Top guest favorite

The modern cabin exterior features a dark blue facade with a wooden front door and expansive deck. A hammock is gently hung on the upper level, surrounded by lush green trees. Firewood is neatly stacked near the entrance, enhancing the outdoor atmosphere.

Cabin in Hillsdale

4.98 out of 5 average rating, 44 reviews

Modern hilltop chalet-style cabin @ Copake Lake

A charming yellow cottage is framed by green trees and a bright blue sky. The exterior features a spacious front porch with large windows and white railings, inviting natural light. Steps lead to the entrance, surrounded by well-kept grass and a few decorative plants.

Cabin in Bethlehem

4.9 out of 5 average rating, 30 reviews

Swim, fish, kayak & RELAX!

Top guest favorite

The cabin is surrounded by lush greenery, with warm lights strung across the deck creating a cozy ambiance. Large windows reflect the evening glow, showcasing a welcoming entrance. The sky transitions from deep blue to vibrant orange, adding to the serene setting of the retreat.

Cabin in Bethlehem

4.95 out of 5 average rating, 79 reviews

Cabin by the lake I Private Beach I Paddle Board

A rustic red cabin is set against a snowy landscape, framed by tall trees. A wooden deck extends from the front, providing access to the entrance. The surroundings are blanketed in snow, creating a serene winter scene.

Cabin in Colebrook

4.94 out of 5 average rating, 94 reviews

Rustic Cabin+ Private Beach Pond, Stars & Wildlife

The cabin is illuminated at dusk, situated on a hillside overlooking a gently flowing river. Leafless trees frame the scene, and scattered leaves cover the ground. The water reflects the soft glow from the cabin, creating a serene atmosphere amid nature.

Cabin in Red Hook

4.97 out of 5 average rating, 87 reviews

Secluded luxury: modern riverfront fishing cabin

A wooden dock extends into a calm lake, featuring two red Adirondack chairs facing the water. A large float is positioned nearby, with trees lining the opposite shore under a partly cloudy sky.

4.87 out of 5 average rating, 54 reviews

Enjoy 43 Acres on Two Ponds!

Cabin in New Hartford

4.98 out of 5 average rating, 50 reviews

West Hill Cabin

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