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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, 149 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

A private dock extends into the calm lake, featuring a sliding board and a set of stairs leading into the water. A rustic playhouse sits nearby, complemented by a wooden bench. Colorful Adirondack chairs surround the area, offering serene views of the surrounding nature.

Cottage in Becket

4.94 out of 5 average rating, 215 reviews

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Sunlight emerges over a tranquil lake, casting golden hues across the water. Tall trees frame the scene, with dense greenery surrounding a wooden deck. The sky displays a blend of soft blues and whites, creating a peaceful natural ambiance.

Cottage in Putnam Valley

4.89 out of 5 average rating, 274 reviews

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

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, 152 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, 110 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, 108 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, 121 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, 393 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..

Top guest favorite

A spacious room features a comfortable bed with a light blue quilt, complemented by decorative pillows. A desk and chair are positioned by a window, with bookshelves in the background. Natural light filters through the windows, creating a welcoming atmosphere.

Guest suite in Morris

4.99 out of 5 average rating, 404 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own lounging/dining area. Guests have their own separate entrance & parking space(s). Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing & just 10 minutes to Washington Depot. We've recently made some updates in response to guests' feedback!

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, 174 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, 172 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, 126 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.

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

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Convenient locations with everyday essentials

Popular amenities for Litchfield County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in New Milford

4.92 out of 5 average rating, 95 reviews

The Getaway: Beautiful Waterfront - New Milford CT

4.99 out of 5 average rating, 182 reviews

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

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, 150 reviews

Lake front retreat - Stylish Berkshire home

A wooden dock extends over the calm waters of Lake Garfield, featuring two rustic chairs and a small table. Lush trees surround the lake, with a blue sky above dotted with clouds, creating a serene outdoor space for relaxation.

Home in Monterey

4.83 out of 5 average rating, 82 reviews

Rustic 3bd Lake Front Country Cottage

Top guest favorite

A spacious outdoor seating area is highlighted with a large yellow umbrella, providing shade over comfortable seating arranged on a stone patio. A serene waterfront view is visible in the background, framed by lush greenery and trees.

Home in Sandisfield

5 out of 5 average rating, 33 reviews

Waterfront oasis in heart of Berkshires

Top guest favorite

The historic home is nestled in a verdant landscape, featuring a charming white exterior with green shutters. A sunroom extends from one side, and trees frame the property, enhancing the serene and rustic setting. The sunlit yard showcases well-maintained greenery.

Home in Pine Plains

5 out of 5 average rating, 7 reviews

Stunningly Designed Historical Icon w/ Hot Tub

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

4.91 out of 5 average rating, 82 reviews

Modern and Stylish Country Lakeside Cottage

A covered porch features comfortable seating with soft cushions, offering expansive views of the lake and surrounding trees during sunset. The warm light casts a golden hue, enhancing the serene outdoor space, while a small table sits in the center, inviting relaxation.

Home in Pine Plains

4.98 out of 5 average rating, 124 reviews

Twin Island Lake House • Hot Tub

Cottage rentals with a kayak

The sunroom features large windows that provide expansive views of the lake, allowing natural light to fill the space. A comfortable seating area includes a cozy chair and decorative pillows, complemented by a small table with plants. The wood-paneled walls add warmth to the environment.

Cottage in Livingston

4.99 out of 5 average rating, 86 reviews

Waterlily Lakehouse - Modern+Waterfront+Retreat

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, 38 reviews

Longview Lakehouse - 5 min walk to private beach

A bright living room features large windows displaying a colorful sunset. A plush sectional sofa, dressed with several cushions, surrounds a round coffee table. A textured area rug adds warmth to the space, enhancing the inviting and comfortable atmosphere.

Cottage in New Fairfield

4.97 out of 5 average rating, 38 reviews

Sunset Cabin Modern Home Kayak FirePit Lake Access

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

4.74 out of 5 average rating, 46 reviews

Lake Cottage in Goshen, CT

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, 104 reviews

Waterfront Joshua Cove Cottage with private beach.

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, 271 reviews

The Cottage at Indian Cove

Cottage in Otis

5 out of 5 average rating, 18 reviews

Lake Escape: Lakefront Cottage in the Berkshires

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

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.

4.81 out of 5 average rating, 21 reviews

Simple, rustic, cozy get away

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

4.91 out of 5 average rating, 32 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, 84 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, 96 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, 89 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

Top guest favorite

An open-floor-plan great room features a large dining table surrounded by natural wooden beams and modern furnishings. Skylights illuminate the space, highlighting a cozy seating area with a blue couch and fireplace. The kitchen area is visible in the background, enhancing the communal feel.

Cabin in Catskill

4.91 out of 5 average rating, 237 reviews

Modern secluded Log Cabin in woods-great location!

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