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Vacation rentals with a kayak in New Haven

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Top-rated kayak rentals in New Haven

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

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Top guest favorite

A well-maintained exterior of a home is framed by lush greenery, showcasing a garden with colorful flowering bushes. A winding gravel path leads through the manicured lawn, inviting exploration of the outdoor space among the trees.

Guest suite in Clinton

5 out of 5 average rating, 13 reviews

Private 2-room suite + bath in beach town

Enjoy 2 rooms + bath. The second floor of my home will be your own private oasis. Large dog (+ cat) on premises (no access to suite). Please be dog-friendly! Spacious bedroom, cozy sitting area, queen bed, TV w/ premium channels. Separate dining/kitchenette with Keurig, microwave & fridge. Brand new private bath with tub/shower. 3 wooded acres by Menunketesuck River. 2-level deck with fire table, patio, propane grill and hot tub. Near premium outlets, beaches, state park, Chamard Vineyard.

Top guest favorite

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

Home in Milford

4.98 out of 5 average rating, 122 reviews

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

A charming waterfront home is seen surrounded by lush trees, with a white balcony and American flag visible. The structure reflects in the tranquil water below, and a dock with a covered area is present in the foreground, alongside various outdoor seating arrangements.

Guest suite in Newtown

4.93 out of 5 average rating, 101 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

A tranquil view of a private beach stretches along the coastline, where gentle waves lap against the smooth sand. Soft clouds dot the blue sky, while beach houses stand in the background, providing a serene coastal ambiance.

Home in Morgan Point

4.95 out of 5 average rating, 44 reviews

Direct Beachfront Modern Cottage on Private Beach

A Modern Beachfront 3-Bedroom House RIGHT ON WATER! AT A GLANCE: ➤ 10 seconds to water ➤ Private beach to enjoy swimming, kayaking, and strolls along the Long Island Sound ➤ Fully updated well stocked kitchen ➤ Grill for outdoor BBQ's ➤ Large deck to catch some rays ➤ Outdoor shower to rinse off ➤ New AC units & ceiling fans throughout ➤ Large TV w/ AppleTV connectivity & WIFI ➤ Only 90 min to NYC, close to Yale in New Haven ➤ Hosted by an experienced Superhost ➤ Sorry, No pets allowed.

Top guest favorite

A scenic waterfront terrace is framed by natural rock formations and lush greenery. An umbrella provides shade over a seating area featuring two Adirondack chairs and a small table, all offering unobstructed views of the water and boats in the distance.

Home in Guilford

5 out of 5 average rating, 12 reviews

Mulberry Seaside Cottage

Enjoy direct water views any time of year in this cozy cottage. Relax on the generous porch swing, eat dinner overlooking the water, watch the sunset on the secret waterfront terrace, and stay active kayaking, biking, and swimming. The large backyard is great for yard games. In the cooler months, cozy up to the outdoor gas fire or inside with a book while watching a stunning winter sunset over the water. Minutes to the charming Guilford green, restaurants, Yale University and train station.

A serene view of the marina at dusk, featuring multiple boats docked in the foreground. The calm water reflects the surrounding landscape and a rising moon, while hillside homes are visible in the background, framed by lush trees.

Loft in Fair Haven

4.88 out of 5 average rating, 94 reviews

Summer Waterside Loft Retreat

Escape to this charming loft on the Quinnipiac River this summer! With a smart TV, full kitchen, bath, and pull-out sofa, it’s a perfect waterfront retreat. Relax on your private balcony or explore the marina. Just off I-91, minutes from New Haven’s pizza scene and Lighthouse Point Beach. On-site, enjoy oysters and cocktails at Fair Haven Oyster Company. Rent a kayak or e-boat, or book a charter to explore the river and Long Island Sound. Rest, relax, adventure, dine and ENJOY ☀️ 🛶 🐟 🍕

A bright living area features large glass doors that open to a beautiful view of the ocean. Comfortable seating includes a sectional sofa and accent chairs, with a modern TV and light wood flooring adding to the ambiance. An umbrella provides shade for outdoor seating on the deck.

Home in Milford

4.92 out of 5 average rating, 38 reviews

Charming 3 bedroom Beach Front Cottage

there is still time to enjoy the fall, the solitude of the beach 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 a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.

Cottage in Guilford

4.99 out of 5 average rating, 106 reviews

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

Top guest favorite

Two kayaks are secured to a wooden fence in the backyard. The kayaks, one orange and one blue, stand out against the greenery of the grass and the fence. The area is well-maintained, creating a welcoming space for outdoor activities.

Home in Milford

5 out of 5 average rating, 110 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, 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!

Aerial view of a tranquil waterfront landscape featuring numerous small islands and rocky shorelines. The serene blue waters reflect sunlight, and a few scattered trees dot the land, enhancing the natural beauty of the coastal environment.

Cottage in Guilford

4.86 out of 5 average rating, 42 reviews

Your own Thimble Islands private cottage!

Escape to your own piece of private paradise! This unforgettable property encompasses 1+ acres of Narrows Island (Thimble Islands/Old Quarry Peninsula) - accessible by car via permanent land-bridge to island. Spectacular one-bedroom cottage with jaw-dropping surround oceanfront and accompanying views; modern and well-appointed. Approx 20 min to Yale, 5-10 min to town green and shops/restaurants. Indulge in sanctuary on an exclusive piece of Connecticut's most coveted shoreline.

A bright dining area is highlighted by large windows that allow natural light to fill the space. A rustic wooden table is adorned with a floral centerpiece consisting of small vases, each housing a single flower. The room features light-colored walls and attractive white chairs.

Cottage in Fairfield Beach

4.98 out of 5 average rating, 123 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 favorite

An oceanfront space features a kayak positioned on the floor, with sunlight illuminating the area. The backdrop showcases expansive views of the water and sky, complemented by picnic tables set outside, visible through large windows. Stairs lead to an upper level, enhancing accessibility.

Home in Milford

4.96 out of 5 average rating, 102 reviews

Oceanfront Retreat: Modern Beach House

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Vacation rentals for every style

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Popular amenities for New Haven kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Fairfield

4.97 out of 5 average rating, 29 reviews

Once a Pond - time and stress slow down.

Top guest favorite

Home in New Milford

4.97 out of 5 average rating, 35 reviews

OWL's PERCH Candlewood Lakefront Rustic Cottage!

The exterior of a newly constructed home features a combination of blue and white siding. Large windows are present on multiple levels, allowing for ample natural light. A staircase leads to the entrance, while parking is available beneath the house.

Home in Milford

4.85 out of 5 average rating, 60 reviews

Newly Built Beach House Getaway

A calm water view is captured from a kayak, revealing gentle ripples reflecting a clear blue sky. Lush green trees line the shore in the background, with a hint of a cottage nestled among them. Sunlight bathes the landscape, emphasizing the tranquil setting.

Home in Short Beach

4.86 out of 5 average rating, 14 reviews

Summer Paradise | Private Beach and Hot Tub Fun

The three-story house features a light grey exterior with multiple balconies on the front. A double garage is located on the ground floor, with large windows above offering a view of the spacious balconies. The welcoming entrance is framed by well-maintained landscaping.

Home in Milford

5 out of 5 average rating, 9 reviews

New build! 1 house from beach

The lake house features a spacious deck overlooking the water, with a private dock extending into the lake. Surrounded by lush greenery, the home has multiple outdoor seating areas and provides easy access to kayaks and boats, enhancing the scenic lakeside environment.

Home in Clinton

4.9 out of 5 average rating, 21 reviews

Boulder Lake House Retreat

Top guest favorite

The kitchen features modern appliances set against white cabinetry, complemented by black bar stools. An outdoor gathering area showcases a circular fire pit surrounded by black Adirondack chairs, with waterfront views in the background. A cozy bedroom displays a large bed with decorative pillows and natural light filtering through the window.

Home in Stratford

5 out of 5 average rating, 7 reviews

Charming Riverview Home *Near Train & I-95

A blue kayak rests on a wooden dock overlooking calm waters. Lush greenery surrounds the inlet, with trees reflected in the water. Soft clouds dot the sky, hinting at a serene evening ambiance.

Home in Fairfield Beach

4.92 out of 5 average rating, 26 reviews

Seaside Home - Walk to Beach & Marina

Cottage rentals with a kayak

A charming waterfront cottage is seen from the water, surrounded by lush trees. A spacious deck with a canopy extends outward, while two individuals enjoy the water on a paddleboard. The shoreline features a rocky edge and a grassy area leading up to the cottage.

Cottage in Branford

5 out of 5 average rating, 11 reviews

Beachfront Cottage Serene Private Beach, Kayaks

Top guest favorite

A two-story cottage features horizontal siding and a distinctive light blue front door. A large window is positioned above the entrance, allowing natural light to enter. The garage is on the ground level, with a small staircase leading to the entryway.

Cottage in Milford

4.92 out of 5 average rating, 52 reviews

Salty Kisses Beach Cottage Milford CT

A beach cottage is presented with a wooden walkway leading from the sandy beach to the entrance. A deck with seating and a kayak is visible, with a backdrop of a clear blue sky and greenery completing the scene.

Cottage in Morgan Point

5 out of 5 average rating, 4 reviews

Caroline Beach Escape

A view of a lake is framed by a wooden deck railing, featuring lush green trees that border the water. Sunlight sparkles on the lake's surface, while a boat can be seen in the distance, contributing to a serene atmosphere.

Cottage in Danbury

4.86 out of 5 average rating, 21 reviews

Lakefront cottage on Candlewood Lake

A serene wooded area is shown, featuring tall trees with lush green leaves. Sunlight filters through the foliage, casting gentle shadows on the forest floor. A glimpse of Candlewood Lake is visible in the background, enhancing the natural beauty of the surroundings.

Cottage in New Milford

4.97 out of 5 average rating, 69 reviews

Waterfront, Wooded Cottage on Candlewood Lake

A serene view of an inlet bay beach is presented, featuring soft sandy shores leading to calm waters. A swan stands gracefully in the water, with the shoreline visible in the background, framed by trees and houses on the opposite side.

Cottage in Short Beach

4.96 out of 5 average rating, 51 reviews

Ret's Coastal Cottage w/Private Association beach

Rugged rocks line the shoreline, leading down to calm water. A wooden dock extends into the bay, providing access to the serene setting. Lush trees frame the scene, showcasing the natural beauty and tranquility of the coastal environment.

Cottage in Short Beach

5 out of 5 average rating, 8 reviews

Shore home in private community, away from it all

The exterior of the house showcases a modern design with a combination of shingles and siding. Large windows provide ample natural light, while a well-maintained lawn is complemented by landscaped shrubs. The house features a charming pathway leading to the entrance.

Cottage in Branford

4.94 out of 5 average rating, 49 reviews

Branford 4 Bedroom Renovated Home With Water Views

Other vacation rentals with a kayak

Home in New Milford

4.92 out of 5 average rating, 100 reviews

The Getaway: Beautiful Waterfront - New Milford CT

The upper deck provides a serene view of the Quinnipiac River, with lush green hills in the background. A small table is set with two glasses and a bottle, creating a relaxed atmosphere on the covered deck.

Boat in Fair Haven

4.89 out of 5 average rating, 56 reviews

Beautiful Quinnipiac River 2-berth Yacht

The exterior of a two-story waterfront home features a charming shingle facade, complemented by a pale blue door. Flower planters with pink blooms adorn the entrance, framed by manicured greenery and a sunlit lawn, inviting guests to explore the property.

Home in North Fork

5 out of 5 average rating, 20 reviews

Waterfront with private dock & bocce court

A two-story house with a light blue exterior features a wraparound porch supported by white railings. Rows of stacked firewood and large windows enhance the welcoming atmosphere, surrounded by tall trees and well-maintained landscaping.

Apartment in Guilford

5 out of 5 average rating, 6 reviews

Lakefront Country Oasis

A three-story beach house features a light-colored exterior with multiple large windows and a covered balcony on the top floor. The architectural design showcases clean lines and a welcoming entrance with a front porch. Nearby trees add a touch of greenery to the setting.

Home in Milford

4.9 out of 5 average rating, 20 reviews

Tranquil beach retreat

A waterfront view captures a colonial home with multiple levels, alongside a charming cabana. Lush greenery and a landscaped yard frame the property, while a dock with boats enhances the lakeside setting. The structure showcases large windows reflecting the natural surroundings.

Home in Danbury

5 out of 5 average rating, 27 reviews

Lakefront 4BR/4BA house, <65 miles from NYC

Top guest favorite

An outdoor patio area features comfortable seating with wicker chairs and a glass-top table, shaded by an awning. Lush greenery and the serene water of Candlewood Lake are visible in the background, completing the tranquil setting.

Home in Danbury

5 out of 5 average rating, 43 reviews

Candlewood Lake - Lakefront Family Getaway 3775sqf

The kitchen features modern cabinetry and high-quality appliances, with a spacious island in the center. Ample natural light streams through multiple windows, highlighting the serene views outside. A cozy dining area is visible in the background, creating an inviting space for gatherings.

Home in Washington

4.9 out of 5 average rating, 20 reviews

A newly renovated country house in Washington

Quick stats about vacation rentals with a kayak in New Haven

Total rentals
20 properties
Nightly prices starting at
G$10,461 GYD before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore