Vacation rentals with a kayak in Westerly

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Popular amenities for Westerly kayak rentals

House rentals with a kayak

Guest favorite
An aerial view captures the home situated near the coast, surrounded by greenery and a winding road. The ocean is visible in the distance, featuring rocky shores and gentle waves. Nearby houses are positioned along the shore, creating a scenic coastal atmosphere.
Home in Narragansett
4.97 out of 5 average rating, 117 reviews

The Surf Shack - Ocean Views From Every Room

LoriRating, 5 stars1 month ago
Absolutely beautiful! Looks exactly like pics. Hosts were responsive and helpful. I loved how the home was decorated. One of the most beautiful places I have stayed. Amazing views. We can’t wait to return! Highly recommend! Five stars in every category.
Guest favorite
A spacious deck offering unobstructed views of the Westport River features comfortable outdoor seating and a storage bench. The light-colored wooden flooring complements the soft hues of the house’s exterior, while nearby trees provide a natural backdrop.
Home in Westport
4.96 out of 5 average rating, 27 reviews

Riverhouse

WendyRating, 5 stars3 months ago
This was the perfect place for three friends who write and workshop together online to gather in person. The main room of the house is filled with light and what I didn't realize from the listing is the beautiful view from the living/dining room down to the river. The kitchen is well supplied and every room was very clean and uncluttered. The three bedrooms on the first floor are all very nice, with good beds and pillows (one is slightly larger with a king-sized bed), so we were able to decide on our rooms painlessly and none of us had to settle for an inferior room. The large dining table was perfect for spreading out our work as well as for dining, and one of us enjoyed having the furnished basement as her private work space. When we had a problem with hearing a beeping noise, which we initially thought might be a smoke detector battery that needed replacing, Bob was very responsive and helpful in figuring out the cause of the beeping from a motion detector. We plan to come again.
Guest favorite
Home in Coventry
4.98 out of 5 average rating, 102 reviews

Cozy cottage 5 minutes from UConn

AmyRating, 5 starstoday
Jennifer and her partner were very empathetic to our families traveling situation. Their kindness was noted. Thank you! I can't wait to come back. Nothing but peaceful afternoons and awestruck views of the sunrise over the most beautiful lake. My husband actually saw the swan on her nest. 🦢💙
Guest favorite
Home in East Greenwich
4.83 out of 5 average rating, 42 reviews

East Greenwich Waterfront Gem

AnnRating, 5 stars3 weeks ago
Ashley’s place was beautiful. Clean, well decorated and the views were incredible. We rented this for my sister who had a wedding in EG and it’s very close to town and the airport. I would highly recommend.
Guest favorite
A scenic view from a wooden deck showcasing a serene river, with a dock extending into the water. A boat is anchored at the dock, surrounded by lush greenery and clear blue skies, creating a peaceful outdoor atmosphere.
Home in Montville
4.9 out of 5 average rating, 122 reviews

Thames River Cottage · Near Casinos + USCGA

KarenRating, 5 stars4 days ago
Thank you for this little gem! It’s really close by the casinos, lots of restaurants, and fun things to do. Due to the weather didn’t get to use the kayaks/canoes but still had an absolute blast. we hope to come back another time. Thank you for everything!
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.
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 stars5 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!
Superhost
An open door reveals a view of a serene lake beyond a green yard. A wooden walkway leads to the water, framed by lush bushes and trees. Sunlight illuminates the scene, enhancing the peaceful atmosphere of the outdoor space.
Home in Ashford
4.84 out of 5 average rating, 89 reviews

Amazing lake home w/ amenities.

YselssaRating, 5 stars1 week ago
It's beautiful home have beautiful lake views what I Love the most was the lake view and decor of the home felt very homey and it has everything you need and Also coloring books wich I love did coloring of the food too has A pac man video game with me and my parents had lots of fun ...TV programming was good great movies to relax with A popcorn and coke also has very nice big backyard downside is we didn't get to enjoy the backyard because of the weather but next time we will what I love the most very peaceful too wish there was A bigger garbage can but the rest everything was fun and amazing loved the kitchen had beautiful stay and highly recommend this home it's so cute cabin style home thank you for having us God bless....

Cottage rentals with a kayak

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
Cottage in Groton
4.96 out of 5 average rating, 314 reviews

Charming Historic Schoolhouse on Mystic River

ThomasRating, 5 stars1 week 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 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 stars3 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.
Top guest favorite
Cottage in Vernon
4.97 out of 5 average rating, 108 reviews

Vintage Bolton Lake

JeffRating, 5 stars6 months ago
If you are looking for simplicity (which we were) this is the perfect place to. I’ve always wanted to stay at a lake house. We couldn’t have asked for more. Serene, tranquil, beautiful are the proper descriptions of the house and the area. We came to Connecticut to visit my daughter and family and they ended up coming to our place instead. Jason was extremely helpful when needed. We would definitely stay there again!
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, 148 reviews

Go Jump in the Lake!

KellyRating, 5 stars4 months ago
We loved our stay at the cabin! It was clean, the kitchen was well stocked for cooking, and the location was beautiful. We stayed for a few days and celebrated our early family Christmas here. It ended up snowing, which made the surrounding Connecticut forest even more beautiful. We found the cabin cozy and peaceful, with the town just 10 minutes away for anything we’d need. I definitely plan to keep this listing in mind for next time I’m visiting family in Connecticut.

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 stars6 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 image captures a charming cabin nestled among lush trees, located at the edge of a serene lake. The clear blue sky reflects on the sparkling water, enhancing the peaceful surroundings. The cabin features a light exterior, with windows offering inviting glimpses inside.
Cabin in Lebanon
4.86 out of 5 average rating, 14 reviews

Casa Lago

JillianRating, 5 stars7 months ago
I didnt want to leave this little cabin in the woods. It felt rustic but had all the modern amenities you would expect in a home. From the rocking chairs on the porch to the comfy beds, there is nothing I could complain about, even if I tried. Marilyn gave excellent suggestions of places to eat and local current events. We left with fall apples, bellies full of clam chowder, and gigantic smiles!!! We have already started planning our return!
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
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, 38 reviews

Secluded Lake House

AlexandraRating, 5 stars6 months ago
Great find! Hidden cottage away from the road, with lots of space to sit indoors and outdoors. Master bedroom spacious but missing blinds, make sure to bring an eye mask if you want to sleep in! Enjoyed our stay!
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
4.85 out of 5 average rating, 78 reviews

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

AnaRating, 5 stars1 week ago
We enjoyed staying at this cabin very much! We didn’t want to travel far this time. Sometimes it’s hard to find places like this, in the early spring, without having to hike half way down south. Where we can enjoy the peace and quiet yet have a lake/beach etc, with decent weather. Joe’s cabin is very cool. If you enjoy traveling back in time, there are plenty of antiques all over the cabin!
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, 130 reviews

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

EmilyRating, 5 stars6 days ago
This little cabin was exactly what we were looking for! We made a last minute decision to get away from “it all” and couldn’t be happier. We kayaked, we fished, we went hiking, danced to records I haven’t heard in years and played lots and lots of board games! The space was clean, cozy and had everything we needed for our stay. The beds (and couch!) were super comfortable and I loved the antiques/decor!! 5 Stars! 10/10! Highly Recommended! Thanks Joe!
Top guest favorite
Cabin in Voluntown
4.95 out of 5 average rating, 736 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

FrederiqueRating, 5 stars1 week ago
We had an amazing stay at this cabin. Tucked away in the woods right on the lake, it was incredibly peaceful and the perfect place to relax. The cabin itself was adorable, clean, cozy, and had everything we needed. We only spoke to the host (Angela) briefly, but she was so kind and welcoming, and let us know she was available if we needed anything. It truly felt like a hidden gem, and we can’t wait to come 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!

Quick stats about vacation rentals with a kayak in Westerly

  • Total rentals

    20 properties

  • Nightly prices starting at

    $140 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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