Vacation rentals with a kayak in Milford

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Top-rated kayak rentals in Milford

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Guest favorite

A modern kitchen features white cabinetry and a marble-like backsplash. Stainless steel appliances are present, alongside a spacious island with seating. Natural light fills the room through large windows, illuminating the light wood flooring that flows into a living area in the background.

Home in East Haven

4.97 out of 5 average rating, 146 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 favorite

Home in New Fairfield

5 out of 5 average rating, 27 reviews

Direct Lake Access - Priv Dock, Kayaks, EV Charger

Welcome to "Anchors Away", nestled directly on a main artery of Candlewood Lake, CT. 90 min from NYC. Feet from lake edge. Kayaks & EV charger. W/car arrival, stand on your perch, observe the views & cascade down the STAIRS to the private grounds. Drop your bags, grab a towel & cartwheel into the lake. W/ boat arrival, drop your anchor at our private dock. Enjoy 3 BDR 3 full BTH home, with lake access year-round. Walkable community. Sleeps up to 8 maximum. No gatherings. No daytime visitors.

Guest favorite

A spacious deck features a white dining table surrounded by six chairs. A large umbrella provides shade while the ocean is visible in the background, showcasing bright blue waters and a sandy beach under a clear sky.

Home in Woodmont

4.86 out of 5 average rating, 28 reviews

Charming 3 bedroom Beach Front Cottage

The Spring is a great time to enjoy the solitude of the beach and watch as the tide ebbs and flows on warm days and cool nights. Have fun with the whole family, friends or loved ones at our beach front escape. Perfect for some fun in the sun. An amazing Sandbar at low-tide, a deck to relax on and a cozy inside are just a few of our great amenities. There is also a Kayak, Paddle-board and raft to enjoy. Feel free to use the fire-pit or fish off the beach. The opportunities are endless.

Superhost

A contemporary living area features a spacious, dark sectional sofa paired with a wooden coffee table. A textured area rug lies on the floor, while large windows allow natural light to illuminate the space. Artwork is displayed on the walls, enhancing the modern decor.

Apartment in Westbrook

4.86 out of 5 average rating, 29 reviews

Shoreline postmodern apartment

Brand New Construction- Everything shiny and new! Located in the heart of the marine district. This 2 bedroom apartment with pull out couch for a third bed offers postmodern styling, and a wide open floor plan. Just steps from all of the major restaurants, bars, breweries, and beaches in Westbrook ct. Brand new and high end finishes, offers easy access to 1-95, all of the local marinas, and famous gathering places such as Lenny and Joes Fish Tales, Bill's Seafood, and Westbrook Lobster co.

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, 102 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 favorite

The exterior features a charming facade with wooden shingles and a welcoming front porch. Two vibrant blue doors highlight the entrance, surrounded by blooming flower pots and neatly arranged greenery. White columns support the porch roof, enhancing the spacious feel of the entryway.

Home in Port Jefferson

4.94 out of 5 average rating, 129 reviews

Harborfront Star

Hang up your car keys and your worries and come visit this beautiful, stylish, coastal gem. Everything that Port Jefferson Village has to offer -- the marina, Harborfront Park, restaurants, clubs, shops, galleries, skating rink, green market, Danfords -- is all within easy walking distance. So come enjoy being in the middle of the action -- and the cool breezes off Long Island Sound -- at the Harborfront Star. We are dog friendly and have a pet fee of $65 per dog (max of 3 dogs).

Top guest favorite

An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Guest favorite

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, 377 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..

Guest favorite

The exterior of a newly renovated cottage features a sloped roof with skylights. A front porch welcomes visitors, and a driveway leads to a garage. Outdoor seating is provided with a picnic table and an umbrella visible in the background amid a landscaped area.

Guesthouse in East Hampton

4.93 out of 5 average rating, 42 reviews

Family-Friendly Lakeside Cottage

Newly renovated lakeside cottage with stunning views. 2 bedrooms with king beds and a pull-out couch, 1.5 bathrooms - 30 second walk to the lake - Fully furnished and equipped - Private rock patio with picnic table and grill - Washer and dryer in unit - Desk for working from home - 2 Kayaks and 2 paddle boards are available for use - Short walk or drive to restaurants, and shops Perfect for romantic getaways, family vacations, or visiting family locally.

Guest favorite

Home in Danbury

4.88 out of 5 average rating, 141 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 favorite

An outdoor deck features a dining table surrounded by six chairs, positioned over the water. The scene includes a marina with boats and lush greenery. A tranquil sunset casts soft hues across the landscape, enhancing the serene environment.

Cottage in Flanders

4.9 out of 5 average rating, 39 reviews

Bayside bliss - Charming 2bdrm on the water w dock

Lovely 2 bedroom cottage located on the water with your own private dock. 2 queen beds, 1 bathroom, and full kitchen. Enjoy a swim and outdoor shower after a blissful kayak along the shores of the Peconic Bay. Easy access to the North and South Forks of Long Island, famous wine trails, Ocean Beaches, and amazing farms. 2 kayaks included in the rental. Experience the food, drink, and beautiful scenery with a short drive to all of the Hamptons.

Guest favorite

A view of Long Island Sound is presented, showcasing calm waters under a clear blue sky. The shoreline is lined with rocky outcrops and greenery, while a bench is positioned along the road for leisure. Gentle waves create a serene atmosphere.

Apartment in Branford

4.95 out of 5 average rating, 22 reviews

Ocean front 1 bedroom apartment

This charming apartment is across the street from LI sound and has an outdoor shower for your use. It has been completely remodeled, including appliances and is large at 1300 sq ft. This is the ideal location for 2 people to unwind and get away from it all and enjoy the beach, put your kayaks in 50’ from property or enjoy excellent restaurants and attractions along the Connecticut shore line.