Vacation rentals with a kayak in Westerly

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Popular amenities for Westerly kayak rentals

House rentals with a kayak

Guest favorite
Home in North Stonington
4.95 out of 5 average rating, 73 reviews

Lakeview

VeronicaRating, 5 stars4 days ago
From the moment we walked in, we felt at home. The home was very clean and well stocked. The outside patio furniture on the deck with the view of the lake was a huge bonus for eating meals, and playing games with our family. The location for us was great, not a long drive to the aquarium, many museums and other fun things to do.
Top guest favorite
A spacious covered deck is highlighted by comfortable seating, including wicker chairs and a red sectional sofa. The deck overlooks a serene lake, with clear skies and distant hills visible in the background. A dining table is present, perfect for outdoor meals.
Home in Preston
5 out of 5 average rating, 51 reviews

New Lake House w/Game Room&Views

YotamRating, 5 stars6 days ago
Our stay here was amazing! So much attention to detail was put into every aspect of this home. It was spotless and very well maintained. We enjoyed being able to use the kayaks, paddleboards, and canoe. We never felt like something was missing and never had a hard time finding what we needed. It is such a quiet and peaceful area and we spent a lot of time just sitting by the water relaxing. We loved being able to have a fire right by the water as well. The downstairs game room/theatre was a blast as well. Overall I would 100% book a stay here in the future and highly recommend it.
Guest favorite
A lakefront home is showcased against a clear blue sky, with a spacious deck extending over the water. Adirondack chairs are arranged on the green lawn, offering views of the lake and surrounding trees. The exterior features large windows and a neutral-colored finish.
Home in Voluntown
5 out of 5 average rating, 5 reviews

Lakeside, A New Waterfront Home on Beach Pond

DebbieRating, 5 stars3 months ago
The house was beautiful and scenery breathtaking. We loved watching the ice fishing, skating and go carting on the lake! We even went out on the frozen lake! It was close to my daughter’s home in Voluntown…. Only 4 minutes away! The kitchen was well stocked and we had everything we needed. They went above and beyond as we were there to celebrate my granddaughters’ first birthday! They left a gift for her and some welcome gifts for us too! Amazing!! They brought a table and chairs for extra seating!! Phil and Staci were amazing hosts and always responsive. We would definitely consider staying here again.
Guest favorite
A spacious living area features a white sectional sofa and leather armchairs, arranged to face large glass doors that provide views of the beach. Natural light fills the room, highlighting warm wood paneling and a cozy, inviting atmosphere. A dining table is visible in the background.
Home in North Fork
5 out of 5 average rating, 12 reviews

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

TimothyRating, 5 stars1 month ago
We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!
Top guest favorite
The exterior of a three-story house is depicted, featuring light blue siding and white trim. A two-car garage is visible beneath the elevated main level. Multiple balconies provide outdoor space, while flowerbeds with greenery are located in front of the home.
Home in Galilee
5 out of 5 average rating, 23 reviews

Monthly Kayak & Paddle Board Retreat

RobertRating, 5 stars4 days ago
For 3 couples, this was the perfect place to stay. It was comfortable,relaxing and close to everything we were interested in.
Top guest favorite
Home in Charlestown
5 out of 5 average rating, 70 reviews

2 Acre Lakefront Getaway (Kayak/Firepit/Fishing)

RobertRating, 5 stars2 weeks ago
Staying at Daniela’s place was great! Super easy to find and get into the peaceful house on the pond. Even though it was pet friendly, the house was spotless and had no wear or tear from previous visitors. It was great that they had child gates at stairs too! The dog loved going out in the canoe and swimming in the pond! Great place overall!
Top guest favorite
A spacious three-story home is set on a lush green hillside, surrounded by colorful fall foliage. The structure includes a combination of stone and wood features, with large windows and a screened-in porch offering views of the landscape. A well-kept garden area is visible in the foreground.
Home in Stonington
4.96 out of 5 average rating, 24 reviews

Stonington Home w/ Spectacular Views.

MarkRating, 5 stars2 weeks ago
All I can say is WOW ! The house was huge, very well maintained, property was amazing and lots of room for the dogs. I Have been going to either lake or waterfront houses on Airbnb for 5 years within the State of Ct and this place blows all of them out of the water, starting with Natalie. What you see on the website is what you get and more. I used to run hotels, and I am very aware how hard it is to WOW someone, and this place exceeded my expectations. Thank you so much Natalie and your family.
Guest favorite
A dining area is set with a light wooden table and white chairs, positioned beneath a modern chandelier. Large windows frame scenic views of Ninigret Pond, with a private dock visible outside, surrounded by greenery and blue skies.
Home in Charlestown
4.96 out of 5 average rating, 48 reviews

Waterfront home with dock, kayaks & paddleboard

Chris And CorinaRating, 5 stars6 months ago
Perfect stay! The location was private, beautiful and safe and also close by to Oceanside restaurants. The house was perfect for my husband, toddler and infant with lots of room to run around outside. Waking up every morning to coffee with a sunrise over the pond and the fireplace on was heaven. Thank you for the magic memories!

Cottage rentals with a kayak

Guest favorite
Two colorful kayaks are positioned on a concrete dock, with the calm waters of the bay extending into the distance. The sky above is clear with some soft clouds, reflecting a tranquil outdoor setting.
Cottage in Westport
4.9 out of 5 average rating, 105 reviews

Kayaks and Glimpses of Westport Bay

DeborahRating, 5 stars9 months ago
Linlin was a wonderful host and we loved this adorable cottage. It was incredibly clean, while still being warm and welcoming for us (and our pup). It's a little farther from the water than we had anticipated, but it's a relatively short and private walk to a dock with kayaks and beautiful views. Highly recommend!
Top guest favorite
A vibrant yellow kayak rests atop a wooden rack, accompanied by a red and blue paddleboard below it. The grassy area is bordered by a wooden fence and a beige house can be seen in the background.
Cottage in Narragansett
5 out of 5 average rating, 223 reviews

♥CozyGetaway-Narragansett-15min to Newport-HotTub♛

JudelieRating, 5 stars2 weeks ago
We had a wonderful stay at Leann’s! The home was absolutely lovely—clean, cozy, and beautifully decorated. The amenities were just what I needed for a relaxing getaway. Leann was a great host, and we truly can’t wait to come back. Highly recommend!
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
4.96 out of 5 average rating, 107 reviews

3 Bedroom Cottage Gem

MontagueRating, 5 stars3 days ago
Loved our stay! This is a gem of a house—it’s gorgeously decorated and equipped with everything you need to feel immediately at home. Shelter Island is one of my favorite places and this home made it feel all the more special. Thank you, Christopher!
Top 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, 112 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

OliviaRating, 5 stars1 month ago
My sister, dog and I stayed at the cottage for the weekend and had a great experience! Erika is a wonderful host and the property is beautiful. The cottage itself was exactly as pictured. Breakfast in the inn, cooked with natural and organic ingredients, is an absolute must. The location of the inn is great as well, with direct access to the Lantern Hill trail (which our dog loved) and only a short drive from downtown. Would definitely recommend staying here!
Top guest favorite
Cottage in Vernon
4.97 out of 5 average rating, 112 reviews

Vintage Bolton Lake

AmberRating, 5 stars2 weeks ago
We enjoyed our time at Vintage Bolton Lake Cottage. The place is cute, peaceful and quiet. Not having a TV was perfection! Kayaking was fun. Nice bass too! Top notch experience. Jason checked in to make sure we didn’t need anything or have any concerns mid stay, which I appreciate. Phenomenal host. Would love to go back!
Guest favorite
The exterior of the cottage is shown, featuring a sloped roof and grey shingles. A front porch is visible, with a flag displayed on one side. Lush green grass and landscaping surround the home, while trees provide a natural backdrop.
Cottage in Lebanon
4.87 out of 5 average rating, 150 reviews

Go Jump in the Lake!

KirstenRating, 5 stars1 month ago
Easy to find and access. Clean and neat. Looked just like the pictures! It was what I looking for when booking! Yeah!! Host responsive and friendly.
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, 106 reviews

Beautiful lakefront retreat just 15 mins to casino

NicoleRating, 5 stars2 weeks ago
Fantastic! The cottage is cozy and clean, had everything we needed and the views are gorgeous! We loved our stay and highly recommend this beautiful cottage!
Top guest favorite
The newly renovated house is set against a backdrop of trees, featuring a charming exterior with grey siding and a brick chimney. A small porch is visible, and colorful autumn leaves are scattered across the front yard, enhancing the welcoming appearance.
Cottage in Colchester
4.97 out of 5 average rating, 174 reviews

Lakefront peaceful getaway cottage

JamesRating, 5 stars2 weeks ago
What a wonderful and peaceful location! Doreen was very responsive and exceptionally helpful. The pictures are spot with a very clean and well stocked home. Amazing views from the bedroom and second floor deck. Amazing place to fish, kayak, and just enjoy the scenery! Enjoyed hiking nearby, great food in the area and a very scenic location to relax.

Cabin rentals with a kayak

Guest favorite
A small marina cabin in a tranquil setting is visible, with colorful kayaks neatly stacked on a rack. A red kayak rests on the water's edge, ready for use. The cabin features large windows and is surrounded by natural greenery, creating a serene atmosphere.
Cabin in Stonington
5 out of 5 average rating, 13 reviews

Mystic Area Waterfront Cabin #3

JoyRating, 5 stars7 months ago
Clean and cozy cabin. Close to Mystic without being right in the thick of it. We enjoyed a night by the fire with a friendly local fisherman. It worked nicely for our short trip to the area.
Superhost
The exterior of a rustic cabin is presented, featuring a red wooden façade with a welcoming porch. A ramp leads to the front door adorned with a decorative window. Lush greenery surrounds the cabin, enhancing its natural setting.
Cabin in Lebanon
4.88 out of 5 average rating, 17 reviews

Casa Lago

NafisRating, 5 stars4 weeks ago
Marilyn’s place was great! Very peaceful. Lake access was awesome. Warm neighborhood. The kitchen was a bit tricky to navigate, but Marilyn had detailed instructions. We enjoyed our stay. I would recommend Marilyn’s place.
Guest favorite
A collection of colorful kayaks is neatly arranged on a rack by the water, adjacent to a light blue cabin. A red kayak is positioned at the water's edge, ready for use. The area features a peaceful marina setting with boats visible in the background.
Cabin in Stonington
4.95 out of 5 average rating, 21 reviews

Mystic Area Waterfront Cabin #1

KatelynRating, 5 stars2 weeks ago
Paul was a wonderful host! He was great with communication, proactive, and accommodating. The cabin was beautiful and awesome location right on the marina. We would highly recommend to our family and friends!
Guest favorite
A well-maintained grassy area leads to a serene lake with clear blue water. Two chairs and a fire pit are arranged on the lawn, providing a space to relax. Lush green trees surround the scene, enhancing the natural beauty.
Cabin in North Stonington
4.95 out of 5 average rating, 40 reviews

Lakeside Landing

SusanaRating, 5 stars2 weeks ago
This was a weekend getaway for our anniversary. We were pleasantly surprised with the quiet and peaceful surroundings. Everything is exactly like the pictures. The neighbors had a large party and we did not hear a thing inside the cabin! It rained most of the days but we were very comfortable. If you love nature, you will love this place. Bring your hiking boots and your binoculars for bird watching. There are several ponds nearby for fishing and you may consider visiting the local wineries. Hope to come back again!
Guest favorite
Several colorful canoes and kayaks are neatly arranged near the edge of a tranquil pond, surrounded by lush greenery. A wooden dock extends towards the water, with a comfortable seating area visible in the background, adding to the serene outdoor setting.
Cabin in Foster
4.95 out of 5 average rating, 40 reviews

Secluded Lake House

JulieRating, 5 stars3 weeks ago
Had a great time in this peaceful wonderful setting. Saw and heard maybe 40 bird species. (Using Merlin app). Frogs and turtles too!everything we needed! Beds are very comfortable!
Superhost
The cabin is positioned near Lake Chaffee, featuring a deck area with seating for outdoor relaxation. Surrounding trees add a natural backdrop, while the sunset casts warm light over the landscape. The tranquil lake reflects the colors of the evening sky.
Cabin in Ashford
4.86 out of 5 average rating, 84 reviews

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

MattRating, 5 stars2 weeks ago
Loved staying at Joe’s lake house. It was quaint and cozy, perfect for a weekend out of the city. Had all the accommodations for us to cook groceries, allowed for a fun time kayaking around the lake and making s’mores by the fire. Great stay!!
Top guest favorite
Cabin in Voluntown
4.95 out of 5 average rating, 741 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

ParamRating, 5 stars2 weeks ago
This cabin was a wonderfully cozy stay for my group. One thing to note is the cabin is on a shared property with other buildings, including the sauna. The lake was beautiful and the Finnish Sauna next to the lake was a very unique touch that I'm glad we got to experience. Angela was a great host and provided clear communication on how to get to the cabin and check in/out. The cabin was compact but had all the bedding fit into it and even a bench inside. The fridge, microwave, and stovetop were all welcome additions to the cabin as well and we never had an issue with electricity. Definitely check this place out if the amenities interest you and you are passing through Connecticut.
Guest favorite
The blue exterior of the cottage is complemented by a row of colorful paddles displayed against the wall. Lush greenery and flowers frame the base of the house, with a view of the lake visible to the side through the trees.
Cabin in Coventry
4.88 out of 5 average rating, 135 reviews

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

MariaRating, 5 stars2 days ago
Joe's Cabin was exactly as described in the listing. Beautiful, peaceful neighborhood, and right next to the lake. Our family came into town for an event and the cabin was the perfect place to relax and unwind. Every part of the home was clean, beds were very comfortable, and every amenity was available if needed. Host was very responsive and communicated well. We will definitely be back.

Quick stats about vacation rentals with a kayak in Westerly

  • Total rentals

    20 properties

  • Nightly prices starting at

    G$29,290 GYD before taxes and fees

  • Total number of reviews

    760 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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