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Vacation rentals with a kayak in Greenport West

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Top-rated kayak rentals in Greenport West

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A beachfront house with a wooden exterior is depicted, featuring multiple windows adorned with green planters. Soft sand covers the area in front, leading to the water, which reflects the clear blue sky. A small chair is visible on the sand, emphasizing the serene beach setting.

Home in North Fork

4.89 out of 5 average rating, 27 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

A spacious living room is highlighted by a unique whale wall art piece and a cozy seating arrangement. A comfortable gray sofa is paired with a nautical-themed chair. Large windows allow natural light to fill the room, creating a welcoming atmosphere.

Home in New London

4.87 out of 5 average rating, 143 reviews

Beauty and the Beach!

Welcome to Beauty and the Beach, where you can come and relax with the whole family or come alone to get away from the busynesses of life! The property is located within an 8 minute walk to Ocean Beach Park and a block away from Alwife cove. With all year recreation. we are located within a short distance to: - Coast Guard Academy -Navy Sub Base -Mohegan Sun -Historic Mystic -Shopping and Great Dining Experiences! -Scenic hiking trails Come and embrace the New England Salty Life!

An aerial view provides insight into the waterfront cottage's layout, showcasing the grassy yard surrounding the home. A patio area with seating is visible, alongside a garden shed and trees offering shade. The peaceful lake borders the property, enhancing the serene environment.

Home in North Fork

4.89 out of 5 average rating, 37 reviews

Waterfront NoFo Cottage w/ public beach access

Enjoy this waterfront cottage overlooking Marion Lake surrounded by lush landscape and wildlife. Experience the local Vineyards, take a leisurely stroll in downtown Greenport, ferry to Shelter Island, drive to Orient, or discover local hiking trails. Savor the culinary delights at the area's great restaurants, with fresh seafood and farm-to-table dining. Nestled between Greenport and Orient Point, East Marion provides access to all the North Fork has to offer. Rental Permit #1060

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, 107 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

A waterfront home is seen with a spacious deck overlooking the calm water. Lush trees frame the property, and a boat is docked nearby. The house features large windows and multiple outdoor seating areas, blending into the natural surroundings.

Home in The Hamptons

4.98 out of 5 average rating, 103 reviews

Breezy Waterfront Home With private Dock

This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

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, 105 reviews

Cozy Riverside Loft Getaway | New Haven

Escape to this charming Fall Foliage Loft on the Quinnipiac River! With a smart TV, full kitchen, bath, and pull-out sofa, it’s a perfect waterfront retreat. Enjoy autumn sunsets from your private balcony or stroll the colorful marina. Just off I-91, minutes from New Haven’s pizza scene and Lighthouse Point Park. On-site, savor oysters & cocktails at Fair Haven Oyster Co. Rent a kayak or e-boat, or book a charter to explore the river & Sound. Rest, relax, adventure & ENJOY 🍁🔥🍕

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in The Hamptons

4.85 out of 5 average rating, 112 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

Top guest favorite

The beachfront home features a wrap-around balcony and large windows that provide views of the shore. The exterior is surrounded by a stone wall and sandy beach, with a staircase leading down to the water from the deck.

Home in North Fork

5 out of 5 average rating, 14 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

Top guest favorite

The exterior of a two-story, grey-shingled building is showcased, featuring multiple windows aligned symmetrically. A well-maintained garden with colorful flowers and greenery surrounds the entrance, which includes a modest front door. A gravel path leads to the property, set against a cloudy sky.

Cottage in Clinton

4.98 out of 5 average rating, 106 reviews

Guest House at the Marina

Traveling nurses, academic rentals happily considered! A beautiful, modern one bedroom apartment on the second floor with a gorgeous view of the Indian River and tidal marsh. It is 600 sq feet, completely renovated, with a queen size bed, a well-appointed kitchen & bathroom. Walking distance to the Clinton train station. Stays in-season include use of 2 kayaks or SUPs per day (2 hours) provided by Indian River Kayak from Memorial Day to Labor Day.

A spacious lawn is surrounded by mature trees, providing shade and greenery. A vintage home is visible, with outdoor seating and a grill setup nearby. Gravel paths lead through the property, inviting exploration of the shared outdoor space.

Home in Rocky Point

4.88 out of 5 average rating, 250 reviews

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

Top guest favorite

A sunlit porch area features a spacious bed adorned with a white quilt and colorful accent pillows. A striped rug lies on the floor, while wicker furniture and large windows create an airy atmosphere. Natural light fills the space, offering views of the outdoors.

Cottage in Guilford

4.94 out of 5 average rating, 275 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.

Top guest favorite

A traditional New England-style house features a front porch supported by white columns. Two white chairs and a small table are arranged on the porch, complemented by a dark front door. Large windows allow natural light to fill the space, surrounded by green landscaped areas.

Cottage in Shelter Island

4.97 out of 5 average rating, 115 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

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Popular amenities for Greenport West kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Top guest favorite

A sunset view over Jordan Cove is captured, showcasing vibrant pink and orange hues blending into the evening sky. The American flag gently flutters in the foreground, while the calm water reflects the colorful display, creating a serene atmosphere.

Home in Waterford

4.95 out of 5 average rating, 119 reviews

Coastal New England Waterfront Home-The Reed House

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 Saybrook Manor

4.96 out of 5 average rating, 131 reviews

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

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

4.96 out of 5 average rating, 51 reviews

Direct Beachfront Modern Cottage on Private Beach

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, 19 reviews

Mulberry Seaside Cottage

A serene backyard is depicted, featuring a soft green lawn bordered by flourishing plants and flowers. Stone pathways meander gently through the garden, leading towards a view of the water. Trees provide shade, enhancing the natural, peaceful setting.

Home in South End

4.89 out of 5 average rating, 27 reviews

Coastal Cottage on the Water

Top guest favorite

A pair of bicycles, one blue with a wicker basket and one red, are positioned on sandy terrain. Dark, dramatic clouds loom overhead, while a kite soars against a backdrop of sunset hues. The scene captures the coastal atmosphere, with the beach visible in the distance.

Home in Old Saybrook

5 out of 5 average rating, 62 reviews

Great Hammock Getaway | Beaches, Views & Hot Tub

A spacious living room is featured with a dark sectional sofa, accent pillows, and a wooden coffee table. Light wood flooring complements the exposed beams above. Natural light is provided by a nearby window, enhancing the inviting atmosphere.

Home in Old Lyme

4.9 out of 5 average rating, 51 reviews

Rogers Lake House (87) · CT College+Beach+USCGA

Top guest favorite

The exterior of the Secret Stone Cottage is presented, featuring a charming stone facade and a multi-pitched roof. Lush greenery surrounds the property, complemented by a well-maintained lawn and a paved driveway leading to an adjacent garage.

Home in Westbrook

5 out of 5 average rating, 35 reviews

Secret Seaside Stone Cottage

Cottage rentals with a kayak

Cottage in North Fork

5 out of 5 average rating, 22 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

A bright living room area features two light blue sofas, complemented by decorative pillows with coastal themes. A white coffee table sits in the center, showcasing a decorative bowl and a remote. Wooden flooring adds warmth to the inviting space.

Cottage in Niantic

4.99 out of 5 average rating, 77 reviews

Little Gem Waterfront beach home/ cottage

A light-colored boat is anchored in calm water, surrounded by lush greenery. Reflections of the boat can be seen on the still surface, while distant homes are visible along the shoreline under a clear blue sky.

Cottage in The Hamptons

4.87 out of 5 average rating, 91 reviews

Waterfront Beach Home & Garden —AC, BBQ, Kayaks!

Top guest favorite

The image features a serene waterfront scene, highlighting a private dock that extends over the calm water. A cozy seating area is visible on the deck, surrounded by lush greenery. In the background, a spacious cottage is framed by tall trees, providing a peaceful retreat.

Cottage in North Fork

4.98 out of 5 average rating, 50 reviews

Stunning waterfront modern farmhouse with dock.

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, 44 reviews

Your own Thimble Islands private cottage!

Top guest favorite

A wooden dock extends into calm waters, featuring an orange kayak secured alongside. Lush greenery surrounds the area, with a bright sun shining overhead and a charming cottage visible in the background, framed by trees.

Cottage in North Fork

5 out of 5 average rating, 26 reviews

The Bay Breeze

Top guest favorite

Two kayaks are positioned near a red shed, featuring distinct colors of yellow, black, and green. The grassy area surrounding them is well-maintained, highlighting the inviting outdoor space of the cottage.

Cottage in Old Lyme

4.98 out of 5 average rating, 50 reviews

Cottage with Roger’s Lake Views

An orange kayak is resting against a wooden fence, with sunlight illuminating the setup. The area features a paved surface and green grass, suggesting space for outdoor activities. Nearby, a table with chairs is visible, indicating a spot for relaxation.

Cottage in East Haven

4.94 out of 5 average rating, 33 reviews

Cozy Cottage with Water Views Steps to the Sand

Other vacation rentals with a kayak

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

4.88 out of 5 average rating, 25 reviews

Boulder Lake House Retreat

A spacious studio apartment is presented, featuring a large circular mirror and light-colored furnishings. Two separate sleeping areas are visible, with one prominent bed framed by bamboo-style headboards. Natural light filters in through sliding glass doors, enhancing the welcoming ambiance of the room.

Apartment in The Hamptons

5 out of 5 average rating, 57 reviews

Spacious apartment in Sag Harbor

A comfortable living area is showcased, featuring two sofas adorned with orange and blue cushions. Natural light fills the space through multiple windows, while a flat-screen TV is mounted on a wooden accent wall. A rug complements the neutral tones of the room.

Home in Old Lyme

5 out of 5 average rating, 32 reviews

Sky of Blue, Sea of Green

A charming two-story home is shown with a light-colored exterior and a sloped roof. A well-maintained yard features a paved driveway leading to a garage. Trees surround the property, providing a natural backdrop, while a small porch with seating is visible on the side.

Apartment in Waterford

4.67 out of 5 average rating, 15 reviews

On Jordan's Cove!

Top guest favorite

A wooden dock extends over tranquil waters, with a bright blue kayak gently floating beside it. The horizon showcases a blend of soft clouds and clear blue skies, offering a serene atmosphere ideal for relaxation and nature appreciation.

Guest suite in The Hamptons

5 out of 5 average rating, 31 reviews

Hamptons Waterfront Romantic King Suite

A spacious wood deck surrounds a heated pool, featuring comfortable lounge chairs. Potted plants add greenery, while lush trees create a natural setting. Two umbrellas provide shade, enhancing the inviting outdoor space ideal for relaxation.

Home in The Hamptons

4.87 out of 5 average rating, 23 reviews

East Hampton 3 bedroom with pool

Top guest favorite

An outdoor deck features a large dining table surrounded by multiple chairs, shaded by a sun umbrella. In the background, beach chairs and an umbrella are set on the sand, with calm waters extending toward the horizon.

Home in North Fork

5 out of 5 average rating, 29 reviews

Hang by the (Chel)SEA

Top guest favorite

An outdoor pool area features a rectangular swimming pool surrounded by a stone patio. Two lounge chairs with cushions are positioned beside a small glass-top table under a large umbrella. Lush greenery and trees provide a natural backdrop in the distance.

Guesthouse in The Hamptons

4.98 out of 5 average rating, 50 reviews

The “Birdy” Guest house

Quick stats about vacation rentals with a kayak in Greenport West

Total rentals
20 properties
Nightly prices starting at
€ 254 before taxes and fees
Total number of reviews
530 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool

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