Vacation rentals with a kayak in Dutchess County

Find and book unique kayak rentals on Airbnb

Top-rated accommodations with a kayak in Dutchess County

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

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A living area features a ceiling fan above a cozy seating arrangement with a black sofa and bean bags. A round glass dining table is surrounded by four light-colored chairs. Stairs lead to the upper floor, while a glimpse of the kitchen is seen through a nearby window.
Apartment in Saugerties
4.88 out of 5 average rating, 133 reviews

Huge 2 Floor Apartment Available, Est.2020

Spacious newly renovated apartment located in Saugerties NY. My home is near Lake Katrine, Kingston, Catskills, Rhinebeck and Woodstock. 12+, NO PETS, NO EXCEPTIONS!. A portion of what you pay goes to Airbnb. One big bedroom upstairs (Q bed), kitchen, living room, bathroom and gym downstairs. A few minutes away from town(s), shopping centers and Mall. Very close to hike trails and lakes. My home is newly renovated with almost everything new. Please treat my home/things with respect. Creek View.

Guest favourite
A view from a set of wooden stairs reveals a serene landscape by the water. Lush green trees frame the scene, which includes a dock along the water's edge. A vehicle is visible on the gravel driveway, offering a glimpse of the property’s outdoor space.
Apartment in Saugerties
4.89 out of 5 average rating, 199 reviews

Esopus Bend Getaway - 4 min to HITS

2nd floor apartment. Separate entrance, private bath (shower). Comfortably accommodates two people. Charming eat-in kitchen opens onto small deck with Esopus Creek view. Both can be used as work spaces. Short walk to village center. NEW OPTION! “The Sun Studio” with futon sofa/sleeper for 2. Add this beautiful room to your accommodations just across the hall. Best views! Full of light! A desk for your laptop. Space for your yoga mat. $45/night extra, with discounts for longer stays.

Top 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
4.97 out of 5 average rating, 112 reviews

Secluded luxury: modern riverfront fishing cabin

Far from the road, this tranquil and unique modern cabin overlooking state stocked fly fishing and tubing river is under 2 hours from NYC. Sited on a 120 acre property, the towns of Red Hook, Rhinebeck, Hudson and Kingston are all between 10 and 30 mins away. On property hiking and tubing for fun. Our chickens mean you'll have fresh eggs on arrival. Radiant floors, swedish compost toilet, a tesla powerwall and 500 mbps internet make it easy to get away from it all while staying in touch.

Top guest favourite
A spacious living room is highlighted by a comfortable green couch adorned with decorative pillows. A sleek coffee table is centered within the space, while a relaxed dog lies on the soft, natural fiber rug, contributing to the inviting atmosphere.
Home in Saugerties
4.97 out of 5 average rating, 115 reviews

Waterfront, Dog & Family Friendly, Cozy Cottage

El Girasol, "The Sunflower," a sunny, family and pet friendly cottage on the Esopus Creek in the Catskill Mountains. Our home is fully furnished with global & vintage finds. This charming cottage has 2 beds, spacious living room with a big, comfy sleeper sofa and cozy electric fireplace & fully equipped kitchen combined with a dining room. Creek access, BBQ, fire pit, fenced in backyard, & 2 decks makes our home a great destination for a relaxing getaway with family, friends and pets.

Top guest favourite
A wooden dock extends into the calm waters of the Esopus Creek, surrounded by lush greenery. The tranquil surface of the water reflects the surrounding trees, creating a serene atmosphere. Smooth stone steps lead down to the water's edge, enhancing accessibility.
Home in Saugerties
4.96 out of 5 average rating, 311 reviews

Creekside Cottage

Set on the beautiful Esopus Creek, this lovely 2 BR, 2 bath home is perfect for a get-away w/family, friends or a romantic or creative retreat. It's just a 15-20 minute drive to the quaint Village of Saugerties, Kingston, Woodstock & Rhinebeck. Sit & watch the river run by on the screened porch or on the deck down by the river's edge, bbq (4 burner gas stove), play board games, take a kayak or swim in the river. Kitchen w/full amenities. Pets are not allowed unless pre-approved.

Top guest favourite
A waterfront home is shown from an elevated view, featuring an expansive deck with outdoor seating and a gazebo. Colorful kayaks are positioned along the water's edge, with lush trees showcasing autumn foliage in the background, contributing to the serene atmosphere.
Home in Saugerties
4.94 out of 5 average rating, 181 reviews

Waterfront Three bedroom in Saugerties w/ Hot Tub

Welcome to a waterside haven! So peaceful, yet only a mile from the center of Saugerties. You will love this open concept, three bedroom, two full bath, waterfront home with year round outdoor Hot Tub! Swim, kayak, paddle board, fish, relax, BBQ all from your huge front deck. Private, peaceful, quiet on a dead end street. Near hiking, fall foliage, skiing, shops and all the Catskills has to offer. The house is family and dog friendly. See our social media Insta @esopuscreekhouse

Top guest favourite
A spacious living area features a futon decorated with patterned cushions and a striking red pool table. A light fixture with multiple bulbs hangs overhead, while a wall-mounted TV is visible in the background. Large pocket doors separate the living space from the bedroom.
Apartment in Kingston
4.98 out of 5 average rating, 184 reviews

Lovely 1 bedroom apt. with free parking in Rondout

Large 1 bedroom apartment with 10 foot ceilings, located in Kingston Historic Rondout District. Queen size bed and one large futon conversation, there are large pocket doors that separate the bedroom from the living room, pool table, lots of natural light, blackout curtains , air conditioning, claw foot tub, small private patio, 60 inch wall tv, walk to the historic Rondout water front, restaurants, boat rides, trolly, art galleries, Kingston Point Beach and Hudson Brickyards.

Top guest favourite
A serene lakeside view is captured at sunset, with vibrant pink and purple hues reflecting over the calm water. Silhouetted trees frame the scene, and distant hills provide a tranquil backdrop to the picturesque landscape.
Home in Pine Plains
4.98 out of 5 average rating, 133 reviews

Twin Island Lake House • Hot Tub

Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great area for hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.

Guest favourite
A tranquil riverside setting showcases a wooden deck with several chairs facing the water. Soft lights hang from trees, adding a gentle ambiance. A hot tub is positioned nearby, with lush green trees lining the water's edge, completing the serene outdoor atmosphere.
Home in Lake Katrine
4.95 out of 5 average rating, 114 reviews

Peaceful Riverfront Cottage with Private Hot tub

Escape the hustle and bustle of everyday life and unwind in this charming, retreat nestled in the serene beauty of the Catskills. Located in a quiet neighborhood, this cozy home offers a peaceful ambiance with picturesque views of the tranquil Esopus creek. This spacious home is perfect for families or small groups seeking a rejuvenating getaway. Private Hot Tub: Relax and unwind as you soak in the sunset views over the river from your very own hot tub.

Top guest favourite
An aerial view showcases a lakefront cottage with a warm-toned roof, surrounded by lush greenery. Two blue kayaks sit on the water, while a stone patio features a dining area. A fire pit adds to the outdoor space, blending with a wooden boat dock.
Cottage in Livingston
4.98 out of 5 average rating, 107 reviews

Waterlily Lakehouse - Modern+Waterfront+Retreat

The Waterlily House is a Lakefront cottage at the North Twin Lakes in Livingston, NY, located just 2 hours from NYC. The lakefront cottage has been designed and decorated in a Frandinavian Style (Parisian chic and Scandinavian minimalism ). This chic 4 bedroom, 3 bath home, which can sleep up to 8 people, has been designed with an eye for detail, style, and relaxation. Follow us on IG @waterlilylakehouse for any last-minute cancellations/openings

Guest favourite
A winding stone path leads to a rustic stone chimney of the cabin, surrounded by autumn foliage. Small lanterns line the path, casting soft light against the backdrop of trees and textured wooden siding.
Cabin in New Milford
4.94 out of 5 average rating, 192 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!

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, 150 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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