Holiday rentals with a kayak in New Haven County

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Top-rated rentals with kayak in New Haven County

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

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Top guest favourite

Home in Milford

4.96 out of 5 average rating, 27 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.

Guest favourite

Guest suite in Newtown

4.94 out of 5 average rating, 95 reviews

waterfront on Lake Zoar[ SUITE]

Enjoy your private patio overlooking the lake, Or just walk 12 steps to water Edge and visit the cozy lower level and enjoy the swings . Use our kayaks, and don’t forget to bring your fishing pole, go swimming ,or just sit in the sun with a book and listen to the waterfall and you are welcome to sit by the firepit Optional boat dock space, parking Hosts live upstairs Two miles to quaint Sandy Hook center with grocery and restaurants All quests must be register Ninety minutes to Boston/nyc

Top guest favourite

Guest house in Madison

5 out of 5 average rating, 54 reviews

Coastal River Barn Retreat

Spend your days in this newly renovated Coastal Barn Retreat, (which is immediately adjacent to our house). With a modern design and large windows, enjoy views of Neck River. Kayak down river to the Sound at high tide or bike to nearby local beaches with bikes (2) and kayaks (4) provided by owner. Close to town beaches, Hammonasset, Vineyards, Hiking trails. Tons of natural light. Living area is under a cathedral ceiling with forced air heat, air conditioning, and wireless wifi.

Guest favourite

Flat in Guilford

5 out of 5 average rating, 6 reviews

Lakefront Country Oasis

Quintessential New England Getaway Welcome to the perfect escape in a classic New England shoreline town! Whether you're kicking back by the tanquil lake, exploring the area on two wheels or enjoying cozy evenings around the firepit, this peaceful retreat offers the ideal setting to relax and make lasting memories. Amenities for every adventure... your stay includes access to: --4 bikes for scenic rides --3 kayaks. a paddleboard and a rowboat w/ motor --Fishing rods --2 kid's scooters

Top guest favourite

Home in Branford

5 out of 5 average rating, 14 reviews

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with two small private beaches, boulders by the water, large pool, hot-tub, outdoor bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, sweeping staircase, 5 bedrooms plus loft, 3.5 bath plus half bath and outdoor shower by pool. A real oasis! (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed Jan-March)

Top guest favourite

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

Top guest favourite

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 favourite

Home in Branford

5 out of 5 average rating, 51 reviews

Beach House in Private Community on LI Sound

Looking for the perfect getaway for the whole family? Look no further than our charming house located just steps away from a private beach in a family-friendly community on Long Island Sound. Fully equipped with everything you need for an unforgettable vacation, our house includes kayaks and a paddle board for fun in the sun. After a day at the beach, rinse off in our outdoor shower and relax on the peaceful deck with views of the sound. Book your vacation now.

Top guest favourite

Cottage in Guilford

4.94 out of 5 average rating, 262 reviews

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Guest favourite

Tiny home in Milford

4.92 out of 5 average rating, 96 reviews

Beach Cabana

Location, location, location...This is a one of a kind tiny house! Quaint beach cabana - direct waterfront. Full galley kitchen, loft with queen bed, full bath, sitting area with tv etc. Take a walk on the beach or relax by the firepit. Downtown is a short drive with many culinary options to choose from and access to train. The loft has a relatively low ceiling and may be difficult for some to navigate.

Guest favourite

Flat 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.

Guest favourite

Cottage in Branford

5 out of 5 average rating, 10 reviews

Beachfront Cottage Serene Private Beach, Kayaks

Imagine waking up at a serene waterfront cottage overlooking the Branford River, Branford Marina, Branford Point, and a bay that opens up to Long Island Sound. Imagine breakfast or just sipping your coffee on an open deck at water’s edge. Imagine a day at the beach, two supplied kayaks, and beautiful sunsets to complete the day. And all this set in the picturesque neighborhood of Pawson Park.