Vacation rentals with a kayak in New Haven

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Top-rated kayak rentals in New Haven

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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

A two-story home features a light-colored exterior with traditional shutters and a welcoming front porch. The yard is neatly landscaped with greenery and flowers. A wooden deck is visible at the back, providing an inviting outdoor space.

Home in Old Saybrook

4.97 out of 5 average rating, 121 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Guest favorite

A lakeside cabin is framed by vibrant autumn foliage, showcasing a rich red exterior. The structure is positioned on a grassy area with steps leading to the water. The serene lake can be seen in the background, reflecting the clear blue sky.

Home in East Haddam

4.95 out of 5 average rating, 207 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

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.

Top guest favorite

An aerial view captures the cabin situated along the shoreline, surrounded by lush greenery. The property features a private dock and several boats tied up. Nearby houses exhibit a charming lakeside setting, with a mix of greenery and water visible.

Cabin in East Haddam

5 out of 5 average rating, 16 reviews

Lakeshore Cabin with boat dock

Experience family bliss at our Moodus Reservoir home. Enjoy breathtaking lake views, private dock, and kayaks for adventure. Fish, swim, or unwind on the deck. A fully equipped kitchen, grill, and firepit make for perfect family gatherings. Kids will love exploring nature and roasting marshmallows. Close to attractions, yet a serene escape. Just two hours from NYC or Boston, our cozy retreat offers the ideal mix of fun and relaxation. Create unforgettable family memories on Moodus Reservoir.

Guest favorite

A patio area features a circular wooden table surrounded by several chairs, shaded by a large umbrella. Lush green grass leads to a tranquil water view, framed by trees under a clear blue sky, creating a welcoming outdoor space.

Home in North Fork

4.91 out of 5 average rating, 23 reviews

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to October 31st.

Guest favorite

Two kayaks are secured to a light yellow shed, displaying their sleek, curved designs and vibrant yellow edges. Lush greenery surrounds the base, suggesting a natural setting. The kayaks are positioned one above the other, with the top kayak partially overlapping the lower one.

Cabin in Bethlehem

4.93 out of 5 average rating, 27 reviews

Swim, fish, kayak & RELAX!

Non- smoking cottage sleeps six (6). 1st floor queen bedroom, 2nd floor two lofts with two twin beds in each. Linens, towels, dishes, bathroom essentials, Keurig, & full kitchen. 4 kayaks, small row boat, life-jackets, fire pit, gas grill, games, corn hole, badminton. WiFi, streaming TV. Heat, AC and ceiling fans. Access to the lake and private beach. Local wineries, antique shops, and farms nearby. Bethlehem Fair, Garlic Fest, Woodhall school. Great fall color and amazing Stars

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, 128 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

A serene view of a calm lake is framed by lush green trees in the background. Two black Adirondack chairs are positioned on the grassy shore, facing the water. A wooden dock extends into the lake, providing a peaceful spot for reflection.

Cottage in Plymouth

4.94 out of 5 average rating, 113 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!

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.

Top guest favorite

An American flag hangs from a tree, gently waving in the evening breeze. The tranquil waterfront scene is illuminated by soft pink and blue hues from the sunset reflection on the water, framed by lush greenery and outdoor seating nearby.

Cottage in Old Saybrook

5 out of 5 average rating, 98 reviews

Cozy Waterfront Retreat

Serene waterfront retreat! Direct waterfront property on Oyster River perfect for kayaking, fishing, paddle boarding or just soaking up the sun. This cozy cottage with views of stunning sunsets allows guests to relax and unwind. Minutes to local restaurants and shopping, walking/bicycling distance to the towns best beaches; close to outlets and casinos. Quaint, charming cottage with beach decor throughout.