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Holiday rentals with a kayak in New Fairfield

Find and book unique kayak rentals on Airbnb

Quick stats about holiday rentals with a kayak in New Fairfield

  • Total holiday rentals

    Explore 30 holiday rentals in New Fairfield

  • Nightly prices starting at

    New Fairfield holiday rentals start at $321 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,470 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of New Fairfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across New Fairfield rentals

  • 4.9 Average rating

    New Fairfield stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated Accommodation with a Kayak in New Fairfield

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Top Guest favourite
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

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

ValueLocationBackyard

4.98 out of 5 average rating, 179 reviews
Top Guest favourite
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

Cozy Scenic New England rural retreat hike & kayak

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. Family friendly beach on Lake nearby. Pets welcome. Inquire min stay requirements.

Outdoor spacesValueBeach

4.96 out of 5 average rating, 191 reviews
Top Guest favourite
A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.
Home in Putnam Valley

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

ValueLocationParks

4.99 out of 5 average rating, 190 reviews
Guest favourite
A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.
Cottage in Milford

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

ValueOutdoor spacesAir conditioning

4.88 out of 5 average rating, 109 reviews
Top Guest favourite
Cabin in Bethlehem

Lake Retreat, Paddle Board, Swim

Escape daily stress at Deer Ridge Cabin CT, a bright and airy retreat with all amenities. Enjoy the private community beach and paddleboarding at the lake, a 5-minute walk away. Or exploring nearby hiking trails. Only a 15-min drive to downtown Lichfield to indulge in great restaurants and shopping. Experience local wineries. Conveniently located 2 hrs from NYC, this peaceful cabin offers a quick escape to nature while being close to everything! Deer Ridge Cabin CT is your perfect getaway!

ValueOutdoor spacesSleep quality

4.95 out of 5 average rating, 122 reviews
Top Guest favourite
Cottage in South Salem

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.

ValueOutdoor spacesCheckout

5.0 out of 5 average rating, 139 reviews
Guest favourite
A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.
Home in Putnam Valley

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

ValueLocationBathroom

4.94 out of 5 average rating, 138 reviews
Superhost
Home in Stamford

5BR Beach House, Game Room + Huge Backyard

Escape to this spacious 5-bedroom Shippan beach home, designed for families and groups to relax, reconnect and have fun together. Just a short walk from West Beach, the home features a huge private fenced backyard, two large decks, fire pit, game room, pool table, ping pong, foosball and plenty of indoor and outdoor space for everyone to spread out Located just minutes from Downtown Stamford and Metro-North, it’s an ideal home base for family getaways, group stays and corporate retreats

Outdoor spacesLocationCheck-in

4.94 out of 5 average rating, 108 reviews
Top Guest favourite
An outdoor seating area is featured with two ornate egg chairs and a spacious sofa. The furniture is complemented by colorful cushions, and a geometric patterned rug is placed underneath. A stone fireplace is visible in the background, surrounded by trees.
Home in New Fairfield

Hilltop Retreat- Lakefront with Dock

Enjoy all that Candlewood Lake and Squantz Pond State Park have to offer in the comfort of our home. Come reconnect with love ones and relax in the serene surroundings. This waterfront property has a private dock, features 2 bedrooms, 2 full baths, and views from almost every room in the home, plenty of indoor and outdoor entertaining space and a wood burning fireplaces to keep toasty during chilly evenings. Toiletries, all linens are provided. Please read house rules before booking.

LocationOutdoor spacesCheckout

4.95 out of 5 average rating, 103 reviews
Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman

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 two-person kayaks are available for use from May 1 to November 1.

ValueOutdoor spacesSkiing

4.96 out of 5 average rating, 458 reviews
Guest favourite
A wooden dock extends towards a serene lake, surrounded by green hills. A kayak rests on the shore, inviting exploration. The scene is framed by the branches of a tree, adding a touch of nature to the peaceful waterfront view.
Home in Danbury

Candlewood Lakefront Retreat

This beautiful custom-built lakefront house is located only 90 min from NYC. Surrounded by nature, it is serene and peaceful. This spacious and cozy home has panoramic views from the living room, office, and master. The owners have tastefully updated throughout. If you are looking for a truly unique and peaceful retreat on the lake, come have an al fresco morning coffee, or sunset dinner while sitting outside on the deck gazing at the rippling lake.

LocationOutdoor spacesDecor

4.88 out of 5 average rating, 173 reviews
Top Guest favourite
The restored a-frame stone cottage is nestled among trees, featuring a wooden deck and stone steps leading to the entrance. A propane grill is positioned on the deck, with a tranquil wooded backdrop showcasing the colors of nature.
Cottage in Pawling

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.

Outdoor spacesValueKitchen

4.99 out of 5 average rating, 185 reviews

Popular amenities for New Fairfield kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Guest favourite
Home in Milford

Oceanfront Beach House w/ Private Hot Tub

LocationValueAccuracy

4.94 out of 5 average rating, 145 reviews
Guest favourite
The lakeside property features a well-manicured lawn leading to the water's edge, complemented by a dock and a single kayak. Lounge chairs are arranged near a shaded gazebo, with a stone pathway guiding guests towards the house, which is framed by lush greenery.
Home in Greenwood Lake

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC

Outdoor spacesLocationWi-Fi

4.97 out of 5 average rating, 114 reviews
Top Guest favourite
A sandy pathway illuminated by soft lights leads toward a tranquil beach at dusk. Tall grass borders the path, and the horizon showcases a gentle gradient of colors as the sun sets over the calm water.
Home in Miller Place

Ocean House

Outdoor spacesLocationAir conditioning

4.96 out of 5 average rating, 114 reviews
Top Guest favourite
The exterior of a stone cottage is presented, featuring a distinctive sloped roof with wooden shingles. Lush greenery surrounds the home, with vibrant flower beds flanking a stone pathway leading to the entrance. A mix of windows brightens the facade, enhancing the cottage's inviting appearance.
Home in Gardiner

Riverfront Stone Cottage Private/ hot tub/ boats

LocationOutdoor spacesHospitality

4.91 out of 5 average rating, 303 reviews
Top Guest favourite
Home in High Falls

Comfortable & Spacious Country Home - All Seasons

Outdoor spacesLocationRiver

4.98 out of 5 average rating, 121 reviews
Guest favourite
A fire pit is surrounded by four wooden Adirondack chairs on a gravel circle, positioned near a serene waterfront. Lush green trees frame the scene, providing a natural backdrop to this inviting outdoor gathering space.
Home in Lake Katrine

Waterfront Cottage - Hot Tub, Kayaks and Fire Pit

LocationOutdoor spacesView

4.95 out of 5 average rating, 106 reviews
Guest favourite
A serene view of Beaver Pond is presented, with calm water reflecting the blue sky and soft clouds above. Lush green grass frames the foreground, while trees and greenery outline the opposite bank, creating a peaceful natural setting.
Home in Meriden

Relax by the water in a 4 bedroom house

ValueOutdoor spacesWi-Fi

4.82 out of 5 average rating, 141 reviews
Top Guest favourite
A sunlit deck overlooks the serene lake, featuring a glass-top table and comfortable seating. Flower pots add color, while the gentle waves can be seen against the wooden dock. The expansive waterway and surrounding hills create a peaceful backdrop.
Home in Greenwood Lake

The Best Lake House! *Ask About Boat Use Promo*

Outdoor spacesValueAccuracy

4.98 out of 5 average rating, 208 reviews

Cottages with a kayak

Guest favourite
A light-filled living area features a gray sofa adorned with patterned cushions. A wooden coffee table rests on a colorful rug, with a sleek arc lamp illuminating a cozy reading chair nearby. Large windows provide views of the surrounding trees, enhancing the natural ambiance.
Cottage in Poughkeepsie

Be in Nature at this Gorgeous Riverfront Cabin

LocationValueParking

4.91 out of 5 average rating, 396 reviews
Guest favourite
A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.
Cottage in Putnam Valley

Lakefront Cottage near Hudson Valley

Outdoor spacesValueHospitality

4.88 out of 5 average rating, 329 reviews
Top Guest favourite
The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.
Cottage in Bethlehem

Cozy Cottage |Quintessential CT | Pet Friendly

Outdoor spacesLocationWi-Fi

4.99 out of 5 average rating, 170 reviews
Top Guest favourite
A jetted swim spa is positioned on a deck overlooking Lake Garda at sunset. The water's surface reflects soft hues of orange and pink, with serene trees framing the view. The spa displays an illuminated edge, enhancing the tranquil atmosphere of the lakeside setting.
Cottage in Burlington

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

ValueLocationDecor

4.98 out of 5 average rating, 192 reviews
Top Guest favourite
The lakehouse is nestled among tall trees, with a spacious deck overlooking the water. Colorful flowers enhance the natural landscape, while a rocky shoreline leads to tranquil waters. Sunlight filters through the trees, creating dappled patterns on the house and surroundings.
Cottage in Highland Lake

The Mountaintop Lakehouse that Time Forgot.

Outdoor spacesLocationCleanliness

4.97 out of 5 average rating, 390 reviews
Top Guest favourite
A wooden dock extends over calm lake waters, framed by vibrant hues of pink and purple in the sunset sky. Two adirondack chairs are positioned on the dock, inviting relaxation while enjoying the serene views, with softly glowing lanterns along the water's edge.
Cottage in Plymouth

Cozy Oasis, Lakefront with Stunning Sunset Views

ValueLocationCheck-in

4.94 out of 5 average rating, 151 reviews
Guest favourite
A serene view of Walton Lake captures a wooden dock extending into calm waters. The setting sun casts a warm glow over the landscape, reflected in the lake. Lush greenery frames the scene, enhancing the tranquil atmosphere.
Cottage in Monroe

Cozy Lake Cottage

Outdoor spacesValueEV charging

4.99 out of 5 average rating, 205 reviews
Guest favourite
A serene lakeside view is captured, featuring lush greenery and colorful plants in planters. A lounge chair is positioned on the grass, inviting relaxation while looking out over the calm waters of the lake, framed by a backdrop of tree-covered hills.
Cottage in Monroe

Hudson Valley Lakefront Cottage | Nature Escape

LocationOutdoor spacesParking

4.96 out of 5 average rating, 120 reviews

Cabin rentals with a kayak

Guest favourite
A serene pond reflects the surrounding greenery, with kayaks resting on the shore. A cozy cabin is visible in the background, framed by trees. The tranquil setting invites outdoor activities such as swimming or fishing, creating a peaceful natural atmosphere.
Cabin in Colebrook

Rustic Pond Cabin: Nature, Stars & Serenity

ValueOutdoor spacesLaundry

4.95 out of 5 average rating, 129 reviews
Top Guest favourite
Cabin in Kingston

Lakeside Cottage: Boulder's Bluff

Outdoor spacesValueKitchen

5.0 out of 5 average rating, 244 reviews
Guest favourite
The modern cabin is illuminated by string lights, creating a warm ambiance against the dark backdrop of surrounding trees at night. The deck extends outward, providing a welcoming entrance, while large windows hint at the interior’s cozy atmosphere.
Cabin in Red Hook

Design-Forward Riverfront Cabin on 120 Acres

LocationOutdoor spacesCheck-in

4.96 out of 5 average rating, 137 reviews
Top Guest favourite
An open concept living area features vaulted wooden ceilings and large windows offering natural light and forest views. A cozy sofa is positioned in front of a modern coffee table. An adjacent dining area and fully equipped kitchen complete the layout, promoting a spacious atmosphere.
Cabin in Greenwood Lake

Modern Nordic Designed Cabin

ValueOutdoor spacesParking

4.99 out of 5 average rating, 137 reviews
Guest favourite
A spacious living area features high wooden ceilings and large windows allowing natural light to fill the room. Comfortable seating is arranged around a circular coffee table, with a dining area visible in the background. Double doors lead to an outdoor deck surrounded by greenery.
Cabin in Kerhonkson

Scenic View Chalet, Firepit, BBQ, & 2hrs to NYC

LocationOutdoor spacesCheckout

4.97 out of 5 average rating, 207 reviews
Guest favourite
A rustic lakefront cabin is depicted, featuring a stone facade with green accents. Surrounding the home are trees showcasing autumn foliage. A stone staircase leads up to a welcoming entryway, with a white picket fence framing the well-maintained front yard.
Cabin in West Milford

Magical LAKEFRONT Cabin

ValueLocationHospitality

4.91 out of 5 average rating, 129 reviews
Top Guest favourite
Cabin in Red Hook

Luxury Scandi Lakeside Cabin with Woodfired Sauna

Outdoor spacesLocationDecor

5.0 out of 5 average rating, 17 reviews
Top Guest favourite
The exterior of a modern home is set against a vibrant sunset, showcasing a dark wooden facade and large front steps leading to the entrance. Large windows reflect the changing sky, while the surrounding grassy area is landscaped with stones and trees.
Cabin in Marlboro

Cascade-Cabin

Outdoor spacesLocationNearby

5.0 out of 5 average rating, 25 reviews

When is the best time to visit New Fairfield?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$399 NZD$356 NZD$329 NZD$439 NZD$507 NZD$579 NZD$822 NZD$843 NZD$552 NZD$613 NZD$591 NZD$534 NZD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

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