Holiday rentals with a kayak in New Milford

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in New Milford

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

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Guest favourite

Home in New Paltz

4.95 out of 5 average rating, 273 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.

Guest favourite

Home in East Haven

4.97 out of 5 average rating, 147 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Top Guest favourite

Home in Ancram

4.99 out of 5 average rating, 179 reviews

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

All size Dogs & Cats Welcome *Outside backyard is large and surrounded by trees with Firepit, Hammock & Volleyball Net +Watercraft available - Kayaks/Rowboat Swim Platform Indoor Wood Burning Fireplace Fully stocked kitchen and toiletries 10-15 minutes to Bash Bish Falls/Catamount Aerial Park/Ski/Snowboard/Tubing 25-30 minutes to Berkshires Shoe shoeing +November-April: watercraft not available, also weather dependent *Only one neighbor, is to the left, separated by trees and bushes

Top Guest favourite

Cottage in Southwick

4.98 out of 5 average rating, 105 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

Guest favourite

Cottage in Putnam Valley

4.89 out of 5 average rating, 269 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

Home in Morris

4.87 out of 5 average rating, 150 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 favourite

Cottage in South Salem

5 out of 5 average rating, 103 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.

Guest favourite

Cottage in Plymouth

4.94 out of 5 average rating, 114 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

Superhost

Home in Ulster Park

4.88 out of 5 average rating, 228 reviews

Entire lake house to yourself. Great for groups

Lake house is great for family vacations, friend groups. it’s entirely to yourself! It’s early Feb, lake is frozen , there is a bundle of wood supplied, get cozy by the fireplace. Relax enjoy view Screened in porch, pergola fire pit, or deck with gas bbq. Family games in Basement Rec room with pooltable, ping pong, darts. Great for Family, reunions and Work crews love it here. stay a while and remote work in style! Close to Kingston, new paltz, Rosendale,

Guest favourite

Home in Otis

4.96 out of 5 average rating, 108 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

Guest favourite

Home in Danbury

4.88 out of 5 average rating, 143 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.

Guest favourite

Campsite in Lake Katrine

4.96 out of 5 average rating, 171 reviews

Private Waterfront Spring Camping Experience

**WATER IS NOW ON FOR THE 2025 SEASON! Owner operated private single campsite! This quaint little tent and private deck are nestled among the trees on the banks of the Esopus Creek in a great little neighborhood! A way to get back to nature without truly leaving it all behind. A one of a kind private waterfront escape with a fire pit & electric! WATER ACCESS AND KAYAKS NOW AVAILABLE! Enjoy a 2.5 mile stretch of the Esopus creek!