Holiday rentals with a kayak in Fairfield

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Top-rated rentals with kayak in Fairfield

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Guest favourite
The living room features large windows offering views of the river and surrounding trees. A blue sofa and a beige tufted couch are positioned around a wooden coffee table, while a colorful area rug adds warmth to the space. Bright yellow walls enhance the inviting atmosphere.
Home in New Paltz
4.94 out of 5 average rating, 326 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Perched on the water’s edge, you’ll look down from this bright, modern post at an expanse of winding river and broad tree-lined meadows. Let the mellow current and enveloping natural setting satisfy and soothe your senses. This special place is close to everything, making it an ideal launchpad to all the Hudson Valley has to offer. Kingston, New Paltz and Rosendale are all ten minutes away, surrounding you with a plethora of hiking trails, climbing, dining, drinking, entertainment and shopping.

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
4.99 out of 5 average rating, 138 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

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
4.88 out of 5 average rating, 300 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.

Guest favourite
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, 133 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.

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
4.96 out of 5 average rating, 417 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 favourite
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, 430 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!

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
4.88 out of 5 average rating, 163 reviews

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.

Top guest favourite
The interior space features a high vaulted ceiling with skylights, allowing ample natural light. A stone fireplace serves as a focal point, complemented by a comfortable seating area. A wooden dining table and a kitchen island with a butcher block top are also present.
Cottage in Pawling
4.99 out of 5 average rating, 155 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.

Top guest favourite
A dining area features a long wooden table set for meals, with plates arranged on woven placemats. To one side, a bar area displays glassware and coffee equipment. Expansive windows frame scenic lake views, allowing natural light to brighten the space.
Cottage in Putnam Valley
4.96 out of 5 average rating, 197 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging

Guest favourite
The outdoor space features a hot tub surrounded by natural greenery, providing a serene environment. A cozy cabin with inviting lighting is visible in the background, while torches are placed nearby to enhance the ambiance. Gravel pathways lead to both the hot tub and cabin entrance.
Cabin in New Fairfield
4.96 out of 5 average rating, 361 reviews

The Little Lake Cabin w/ Hot Tub, Firepit & Kayaks

Named one of the Best Airbnbs in Connecticut by Business Insider, The Little Lake Cabin is a cozy Connecticut lake cabin perfect for relaxing, hiking, and reconnecting with nature. Just steps from Candlewood Lake and Squantz Pond State Park, enjoy kayaking, evenings by the fire pit, or a soak in the hot tub under the stars. Your peaceful New England getaway awaits, ideal for couples, friends, and nature lovers alike.

Guest favourite
A welcoming living area features a spacious sectional sofa adorned with accent pillows. A coffee table with a glass top, displaying a small vase of flowers, sits in the center. Light filters in through sliding glass doors, illuminating the wood-like flooring.
Flat in Carmel-by-the-Sea
4.87 out of 5 average rating, 311 reviews

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.

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
4.91 out of 5 average rating, 373 reviews

Be in Nature at this Gorgeous Riverfront Cabin

Wappinger Cottage is a Scandinavian-inspired home featuring landscaped gardens leading to the shimmering Wappinger Creek. Inside, contemporary furnishings accented by bold patterns and pops of color create a sophisticated and inviting space. Pets allowed. Air-conditioned as of 8/7/24.

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