Vacation rentals with a kayak in Greenport West

Find and book unique kayak rentals on Airbnb

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Popular amenities for Greenport West kayak rentals

House rentals with a kayak

Guest favorite
A spacious front porch is furnished with two wicker chairs and an ottoman, all featuring blue cushions. A ceiling fan is mounted overhead, contributing to the airy feel. Greenery is visible beyond the white railing, enhancing a connection with the outdoors.
Home in Port Jefferson
4.94 out of 5 average rating, 128 reviews

Harborfront Star

MichaelRating, 5 stars1 day ago
Charming home very well maintained and super clean! This was the perfect location to experience all the local charm of Port Jeff! The house had everything we needed - my family felt right at home the second we walked through the doors. Jennifer was proactive with clear instructions - we would 1000% stay again.
Guest favorite
A charming house exterior is shown, featuring a spacious deck with an umbrella for shade. Kayaks are stored on a trailer beside the house, and a well-maintained lawn surrounds the property. Light filters through the trees against a clear blue sky.
Home in Branford
5 out of 5 average rating, 51 reviews

Beach House in Private Community on LI Sound

DanRating, 5 stars4 months ago
Bill’s place provided a wonderful location for our family of seven to spend our Thanksgiving holiday. The house was clean, uncluttered, and comfortable in every way. The kitchen had everything we could hope to find for meal preparation. The two sitting rooms provided delightful spots for reading, conversation or catching up on the television news. The upstairs bathroom was especially room and well-appointed. While it was winter when we visited, we could tell that this house would be a truly marvelous spot during the summer months as it had a great back deck and was truly only a hundred yards or so from a beach on the Long Island Sound. While it may not be the first choice of those who are on a tight budget, we recommend this home highly.
Guest favorite
An orange two-person kayak is resting on a sandy area near Napeague Harbor. A white stand-up paddleboard lies nearby. The calm water reflects the clear blue sky, bordered by green grass, creating a serene waterfront scene.
Home in Amagansett
4.93 out of 5 average rating, 14 reviews

Amagansett, Waterfront retreat

DanielleRating, 5 stars7 months ago
My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!
Guest favorite
Home in North Fork
5 out of 5 average rating, 17 reviews

Waterfront with private dock & bocce court

AlisonRating, 5 stars5 months ago
We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️
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, 9 reviews

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

KristinaRating, 5 stars3 days ago
Had a wonderful time over Easter with my family and dog. The view was exquisite and the house very comfortable. Eileen was very responsive and even had hair dryers sent over. The house was very well equipped with lots of kitchen staple goods. Just be aware there is no microwave, but there is a very nice Breville toaster oven. Also, there is a large table outside for a group, but only a small table and counter seating in kitchen inside. We didn't have any issue since the weather was perfect for us to enjoy our Easter dinner outside. Overall, a beautiful home and only minutes from Greenport and wineries.
Top guest favorite
The exterior of a charming two-story house is presented, featuring light siding and dark shutters. Window boxes adorned with blue flowers are visible. A small porch with a door leads into the home, accompanied by a stone pathway and neatly landscaped shrubs.
Home in Old Saybrook
4.97 out of 5 average rating, 121 reviews

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

SueRating, 5 stars4 days ago
Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.
Superhost
A sandy area is visible through an open space framed by wooden beams. The calm water of Long Island Sound extends into the distance, with a flag gently waving in the breeze. Rocks and a grassy patch are also seen nearby.
Home in Madison
4.89 out of 5 average rating, 44 reviews

Coastal getaway with water views in every room

KathyRating, 5 stars8 months ago
Meaghan’s place was everything we needed and more! Loved the views, the waves, the sea breeze, the bird observing, the walks to Grass Island, the together time with family in a quiet, secure & well appointed setting. Meaghan equipped us with everything! She was very responsive to answer questions. This is one of those treasured memories. Can’t wait until we get back again to this special location! Thank you!
Guest favorite
A bright and airy living area features high ceilings with exposed rafters and reclaimed wood beams. A red front door adds a pop of color. Comfortable seating options are provided with a white sofa and armchairs, while a wooden coffee table and a dining table accent the space.
Home in Montauk
4.88 out of 5 average rating, 146 reviews

Waterfront House on Fort Pond, MTK

MeganRating, 5 stars6 months ago
Noah was amazingly helpful for a long weekend we took with our two kids. He had a full size folding crib which made sleeping our 3 year old, easy. He keeps a beautiful, well-stocked home, which made it so convenient to cook some meals at home. The location is amazing, only a short drive to town and a priceless view of Fort Pond only steps away. Would love to stay here again.

Cottage rentals with a kayak

Guest favorite
Cottage in North Fork
5 out of 5 average rating, 13 reviews

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

ChristinaRating, 5 stars1 week ago
Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!
Top guest favorite
Cottage in Groton
4.96 out of 5 average rating, 314 reviews

Charming Historic Schoolhouse on Mystic River

ThomasRating, 5 stars3 days ago
This was our second stay here and it was just as nice as the first. Really responsive host and we love sitting outside at night with a drink enjoying the beautiful view. Nice spot where you don't even need to drive anywhere if you want to experience Mystic and even the seaport if you are up for a 20 minute walk. A+ again, thanks so much!
Top guest favorite
A traditional New England house is set in the central village of the island, surrounded by lush green lawn. Tall trees provide shade, and the late afternoon sun creates elongated shadows across the grass, highlighting the inviting outdoor space.
Cottage in Shelter Island
4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Lisagitelson@Gmail.ComRating, 5 stars5 months ago
This is the absolute perfect home for a get away. Everything you need and more is provided. The home is gorgeous, well decorated, and extremely clean. It is even better than the pictures. It feels like a real home, with luxury and artistic touches, not a generically decorated place. Location is perfect, close to it all and still very private. Christopher is an excellent host, responsive, helpful, and gives you your privacy. I can't recommend staying here enough.
Top guest favorite
An aerial view captures the cottage's proximity to the beach, with sandy shores and gentle waves visible. The surrounding area features a blend of trees and homes, enhancing the scenic coastal environment.
Cottage in Guilford
4.94 out of 5 average rating, 262 reviews

The Cottage at Indian Cove

NicoleRating, 5 stars4 days ago
I thoroughly enjoyed my stay at this peaceful cottage. I enjoyed sipping my coffee looking at the view of the cove from the deck and the bird watching from the screen porch was a delight. The bed was comfortable and Gail stocked the kitchen with drinks and snacks! Gail's house is next door but the layout of the deck and screen porch offers great privacy. A perfect place to get away from it all and relax in nature.
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, 44 reviews

Stunning waterfront modern farmhouse with dock.

PatriciaRating, 5 stars3 weeks ago
Returning guest, we had a wonderful weekend at Michelle's idyllic home. Plenty of space for our two families and 3 kids. The kids love having their own space in the "she shed" while the adults enjoy the lakeside views from both the yard and inside the spacious living area. The house is always immaculately clean. Beds and other furnishings are comfortable, and the house is an easy drive to everything the North Fork has to offer. We look forward to returning (again!) soon.
Guest favorite
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, 37 reviews

Your own Thimble Islands private cottage!

LilianRating, 5 stars4 days ago
We had an amazing stay with Sean and Jenny. The property is perfect for a peaceful getaway from the stresses of daily life- unique location, impeccable views, spotless and well furnished house, we were able to unplug and enjoy some nice quality time. Sean is a gracious host, offered lots of local recommendations as well as details of the house that were very helpful. Was responsive for questions and easy to communicate with. Hope to be back one day!
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, 24 reviews

The Bay Breeze

AmandaRating, 5 stars7 months ago
We had a wonderful stay at Daniel’s home in Cutchogue. It was our second stay at one of his properties, and it did not disappoint. The house is just as described, clean and well stocked, and makes for a wonderful landing spot when exploring the North Fork.
Guest favorite
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 Branford
4.95 out of 5 average rating, 44 reviews

Ret's Coastal Cottage w/Private Association beach

KhelenRating, 5 stars6 months ago
This is a lovely house in a lovely location. We enjoyed walking just steps to the little beach. We also liked how it felt removed from the hustle and bustle yet we easily drove into New Haven and surround towns everyday.

Quick stats about vacation rentals with a kayak in Greenport West

  • Total rentals

    20 properties

  • Nightly prices starting at

    $260 before taxes and fees

  • Total number of reviews

    490 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

Destinations to explore