Vacation rentals with a kayak in Long Island

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Popular amenities for Long Island kayak rentals

House rentals with a kayak

Guest favorite
Home in Putnam Valley
4.92 out of 5 average rating, 12 reviews

Lakehouse Woodland Retreat

MildredRating, 5 stars6 months ago
My family and I really enjoyed Elizabeth property very comfortable and quiet, we definitely thinking about coming back soon.
Top guest favorite
A covered deck offers a scenic view of the lake and surrounding autumn foliage. A table with four chairs and two lounge chairs provide options for relaxation. Bright blue skies reflect on the water, creating a serene atmosphere for outdoor gatherings.
Home in West Milford
4.97 out of 5 average rating, 69 reviews

🛶 Lakefront Paradise with Your Own Private Beach🏖

StephanieRating, 5 stars5 months ago
Everything was perfect ! My family and I had a great time. Looking forward to staying here again in the summer.
Top guest favorite
Home in Mystic
5 out of 5 average rating, 98 reviews

Waterfront Retreat on the Mystic River

MikeRating, 5 stars1 week ago
This place is beyond beautiful! The view is so tranquil. I will definitely be coming back !
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 stars1 week 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 shoreline view features soft sand bordered by water, with a green kayak resting beside a blue kayak. A tall tree stands nearby, and an American flag is seen waving in the breeze. The serene lake reflects the surrounding landscape.
Home in Greenwood Lake
4.85 out of 5 average rating, 144 reviews

Aster Place

AzielRating, 5 stars3 weeks ago
Beautiful home! My boyfriend and I had a great time. It’s super clean and the beds were so cozy. Would definitely go back :)
Guest favorite
Home in Freeport
4.97 out of 5 average rating, 38 reviews

Waterfront Getaway Just 20 Min from Bethpage Park!

ToddRating, 5 stars6 months ago
What can you say that hasn't been already said by previous reviewers. John's house in Freeport is a gem. Perfect getway for weekend for our family. We were greeted by a nice bottle of wine and a generous basket of snacks (always a nice touch). The house was spacious and super clean. The beds were extremely comfy and the kitchen was well equipped for anything you may need. So many fun things we really didn't get to take advantage of (Tiki Room, fire pit etc..). But the crowning jewel is the location on the water. If you just want a place to sit and relax as the sun rises or sets (yes you get to see both from the back deck) this is your place. John was a gracious and responsive host. We hope to be back next year.
Top guest favorite
A waterfront home with a modern design is set against a lush green lawn. The property features large windows reflecting the colorful surroundings and includes a dock leading to the water. Two kayaks are visible on the grass, complementing the serene outdoor atmosphere.
Home in South Kingstown
5 out of 5 average rating, 135 reviews

Waterfront Secluded Home with Dock

MireyaRating, 5 stars4 days ago
It is a beautiful, secluded home with a wonderful view of and access to the water on Potter's Pond. The house felt comfortable with a lot of thought for details - the kitchen was well-equipped, lots of pillows on the beds, high quality and a lot of towels in the closets, night-lights, puzzles and games. Made for a wonderful and comfortable stay. We definitely plan on trying to come back!
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
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, 10 reviews

Beachfront Cottage Serene Private Beach, Kayaks

BasilRating, 5 stars8 months ago
We loved it. Redefines “fully stocked” - David’s place had everything we could ask for. The water at high tide was magical. Kayaking, fishing and we found over 100 (literally) hermit crabs.
Guest favorite
A dining area offers a wooden table surrounded by black chairs, with large windows overlooking the lake. Slate flooring complements the bright, airy space, creating a seamless connection to the outdoor views. Natural light fills the room, enhancing the serene ambiance.
Cottage in Putnam Valley
4.96 out of 5 average rating, 156 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

AngeliqueRating, 5 stars1 week ago
Stayed here with some friends for my birthday and it was wonderful. Ben is very friendly, responsive and made sure to take care of us. The views of the backyard were beautiful and peaceful. We also had lots of privacy. Will definitely be booking again in the future!
Guest favorite
A charming cottage is set against a backdrop of lush greenery, with two decks extending toward the lake. Kayaks sit peacefully on the water's edge, inviting relaxation and adventure. Large blue doors and smooth wooden railings create a welcoming entrance to this tranquil retreat.
Cottage in Ledyard
4.89 out of 5 average rating, 195 reviews

Waterfront cottage overhanging the water!

RobertRating, 5 stars1 month ago
We had a beautiful stay at the cabin. The views are stunning and the hot tub was glorious. A lovely escape into nature.
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 stars6 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.
Guest favorite
A queen bed is dressed in a plaid comforter and topped with decorative pillows. A bedside table holds a lamp and a mug, while a wicker chair and a wooden coffee table, featuring magazines, complete the cozy sleeping area. Soft light filters through nearby curtains.
Cottage in Ledyard
4.91 out of 5 average rating, 110 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

KirstenRating, 5 stars2 weeks ago
The cottage was beautiful and the hospitality was just perfect. Will stay again and highly recommend. Our dogs loved the fenced in yard and trails.
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, 263 reviews

The Cottage at Indian Cove

RosalindRating, 5 stars2 days ago
My adult daughters and I thoroughly enjoyed our stay in this peaceful cottage! The cottage was cozy, comfortable, and just the right size for the three of us. The house and kitchen had all the essentials and we enjoyed the treats and complimentary food that Gail provided. We relaxed and strolled down to Indian Cove and Barbra Pine Memorial beaches. Overall, we had a fantastic stay and highly recommend!
Guest favorite
A backyard patio area is shown, featuring a seating arrangement of several chairs and a table. A fire pit is positioned on a stone surface, surrounded by grass and landscaping. The view overlooks the lake, with boats visible in the background and lush trees framing the scene.
Cottage in East Haddam
4.9 out of 5 average rating, 125 reviews

Direct Waterfront Cottage on Moodus Reservoir.

LisaRating, 5 stars3 weeks ago
Stephanie was fantastic at communication prior to our trip. Home was perfect for our stay.
Guest favorite
A spacious living area is featured, with large windows offering unobstructed views of the lake. Comfortable seating includes a sectional sofa and accent chairs, complemented by warm wood tones. The kitchen area is visible, showcasing a large island and wooden cabinetry.
Cottage in Montville
4.95 out of 5 average rating, 102 reviews

Beautiful lakefront retreat just 15 mins to casino

JohnRating, 5 stars3 weeks ago
We had to come to the area for a family funeral, so this was a last minute booking, and Nicole was just the best. She got us in quickly, with less than 24 hours' notice. The house is absolutely beautiful, and overlooks the equally beautiful Oxoboxo Lake. Would recommend this house to anyone needing to stay in the area. Thank you Nicole!

Cabin rentals with a kayak

Top guest favorite
A spacious wooden dock extends over calm lake waters, with a bright yellow kayak and paddles resting on its surface. Lush green hills are visible in the background, reflecting the serene environment.
Cabin in New Milford
5 out of 5 average rating, 8 reviews

Lakefront cabin with private dock on stunning cove

AlekseyRating, 5 stars8 months ago
We stayed here for 7 days with 2 small kids (2 and 4 years old) and wow was it amazing. The home is spacious and has everything we needed inside and outside the house. I could not have asked for anything else from the home and the dock was just so awesome to have, even caught 10+ fish right off the side. We rented a boat for a day from a marina and were able to come in and out of the backyard/house with no problems. I wish we could stay here for a whole month, but have to go back to real life!
Guest favorite
Cabin in Greenwood Lake
4.99 out of 5 average rating, 79 reviews

Modern Nordic Designed Cabin

AlexandraRating, 5 stars2 weeks ago
We had a great stay at this cabin! The location was on a dead end street which made it very quiet, serene, and private. The lake was visible from the back porch of the house & a very close walk away. The house comes with access to a semi-private beach/dock area which is the perfect place to spend the day in the summer. The house was decorated beautifully while being extremely comfortable at the same time. Our host, Kamil, was very responsive. If I had a question or concern he was extremely helpful within a short period of time. All around, really enjoyed this stay & would definitely return when in this area again!
Guest favorite
A spacious deck features two lounging chairs oriented towards the serene lake view. Lush green grass is visible nearby, with trees lining the water's edge. A private dock can be seen in the background, enhancing the outdoor relaxation space.
Cabin in North Stonington
4.94 out of 5 average rating, 35 reviews

Lakeside Landing

KatarinaRating, 5 stars2 weeks ago
Great lakeside retreat! Perfect for our small family!
Guest favorite
A solitary kayak gently glides across the calm waters of a lake surrounded by lush green hills and scattered islands. The serene sky features soft, fluffy clouds, reflecting a tranquil atmosphere perfect for a day of outdoor exploration.
Cabin in New Fairfield
4.96 out of 5 average rating, 324 reviews

The Little Lake Cabin— hot tub, fire pit, & kayaks

AnaRating, 5 stars1 week ago
Super cute interior. Just like the photos. Absolutely pristine, and phenomenal mattresses. Slept incredibly well. GREAT hot tub and fire pit. Very close to the boat launch. So appreciated access to the kayaks and all the hiking recommendations.
Superhost
An aerial view captures the ECHO cabin nestled among lush greenery, with private access to serene waterfront. The structure is framed by trees, highlighting the expansive lawn leading to the lake's edge, providing a tranquil retreat surrounded by nature.
Cabin in Wantage
4.87 out of 5 average rating, 134 reviews

ECHO cabin - lakefront peaceful modern house

VictoriaRating, 5 stars5 months ago
Very cozy, private, clean and feellikehome spot. Beautiful house on the lake with everything you need. Definitely would stay there again and recommend to everyone who is looking forward for a little getaway from busy life. Great host, responds quickly if any questions, clear instructions and info made my stay super comfortable and memorable. Great experience.
Top guest favorite
The outdoor space showcases a vibrant lake view framed by tall trees. A colorful chair sits on the stone patio, providing a focal point as the sun sets over the water, casting soft hues in the sky. Nearby, a hammock is visible among the foliage.
Cabin in Greenwood Lake
5 out of 5 average rating, 5 reviews

Luxury Lakefront Log Cabin

AbeRating, 5 stars4 weeks ago
We had an amazing stay at this lakefront log cabin on Greenwood Lake. The house is huge yet is still extremely warm and cozy with that classic wooden cabin charm. The heating and cooling system are superb and the house includes heated floors in all bathrooms! The views of the lake are absolutely beautiful, rain or shine, of which we experienced both during our stay. It is the perfect spot to unwind and just enjoy the quiet. The house is furnished for indoor all day and outdoor in and out days! The log cabin was truly spotless and had everything we needed, from kitchen amenities to comfy beds. Rameez and Sadaf were incredibly kind and easy to communicate with, which made the whole experience even better. A peaceful, charming, much needed getaway only an hour and a half out from the business of NYC. We will be coming back!
Top guest favorite
A calm pond reflects the surrounding woods, with two kayaks resting on the shore. The lush greenery is complemented by a rustic cabin in the background, partially obscured by trees. A serene atmosphere is created by the harmonious blend of nature and the cozy setting.
Cabin in North Stonington
4.97 out of 5 average rating, 201 reviews

Spring is here at the Cabin! Come check it out.

TaraRating, 5 stars1 week ago
The cottage was perfect. Rocking chairs by the window for when it was chilly, chairs on the deck, chairs by the pond for when it wasn’t. Terrific recommendations from Tim, particularly the Dog Watch Cafe in Stonington Borough. Our stay was exactly the peaceful respite we needed, we just should have booked three nights!
The exterior of a stone cottage is surrounded by lush greenery, with a prominent stone chimney rising from the roof. A gravel pathway leads up to the entrance, framed by shrubs and small trees. The setting offers a natural feel, nestled among the trees.
Cabin in Stratford
4.81 out of 5 average rating, 44 reviews

Beautiful lakeside summer home

SondraRating, 5 stars8 months ago
We had a lovely 5-day stay at the cabin on the lake! It was just what we needed. When the weather was nice, we hung out on the dock - there was a hammock to relax in, chairs in the shed, boats to explore with (I went out in a kayak a few times). Lake was peaceful and pretty. The cabin itself was quirky and nice. Yes, hot inside during the days, but with the fully surrounding screened in porch, there was no need to stay inside! Even when it rained, we could be "outside" without being in the elements. The kitchen was well stocked, coffee at the ready, there were plenty of towels and sheets and bed (though we only needed one!), shampoo/ conditioner in the shower, wood ready for the fireplace, board games and more. Honestly, it had everything you'd want for a little getaway. The spot felt secluded while only 5 minutes away from a supermarket. [Okay, you could hear Rte 8 traffic a bit, but it served as calming white noise!] I'd definitely return again...

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