Vacation rentals with a kayak in Middlesex County

Find and book unique kayak rentals on Airbnb

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Popular amenities for Middlesex County kayak rentals

House rentals with a kayak

Guest favorite
Home in Fairfield
4.96 out of 5 average rating, 26 reviews

Once a Pond - time and stress slow down.

ShivaRating, 5 stars1 month ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Top guest favorite
Home in Rocky Hill
4.96 out of 5 average rating, 28 reviews

Cozy Waterfront Home, With Hot Tub~Rocky Hill, CT

BrentRating, 5 stars1 day ago
I highly recommend staying at the Riverside Blues House. It is in a charming location and a really well thought out property to stay. Liza really put a lot of thought into making the home not only comfortable but also very welcoming. From the moment I walked in the door you can feel the love in every room. The house is extremely clean with plenty of extras that made my stay very enjoyable. Thank you Liza!
Superhost
Home in East Haven
4.96 out of 5 average rating, 100 reviews

Cozy Beach - Direct Waterfront!

SarahRating, 5 stars6 months ago
This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!
Guest favorite
Home in Old Saybrook
5 out of 5 average rating, 40 reviews

Romantic Couples Retreat with Private Sandy Beach

RajRating, 5 stars2 weeks ago
Fantastic cute spot in Old Saybrook. Key things for future guests to know - there is no A/C in the winter months so the air can get a bit stale / stuffy in the house. Plus there is no washing machine / dryer in the house, so defo bring enough clothes!
Top guest favorite
Home in Preston
5 out of 5 average rating, 52 reviews

New Lake House w/Game Room&Views

YotamRating, 5 stars1 week 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.
Superhost
Home in Newtown
4.86 out of 5 average rating, 7 reviews

Serenity by Lakefront Cottage!

LuisRating, 5 stars3 weeks ago
Definitely recommend will be there another time thanks
Top guest favorite
Home in Milford
5 out of 5 average rating, 96 reviews

Oceanfront Retreat: Modern Beach House

ShannonRating, 5 stars1 week ago
We had a relaxing overnight with our two pups! The bay/sound area is so peaceful. Our dogs enjoyed swimming before the tide came in and we kayaked along the shoreline. The inside was stunning and had everything you needed and more! We door dashed lobster rolls from the Bonfire Grille nearby (10/10) and ended the night in the hot tub! Coffee on the sunny patio was a great perk, too! Thanks again!!
Top guest favorite
Home in Old Lyme
5 out of 5 average rating, 22 reviews

Sky of Blue, Sea of Green

KaylaRating, 5 stars4 days ago
This house had so many amenities and was exactly as described! We enjoyed having access to grills, a hot tub, game room, and all of the household/beach necessities! The house and game decor were super cute and the adults loved the competitive scrabble game on the wall. There was a small ant problem in the kitchen (which the owner was aware of) that was there despite attempts to keep the dishes and garbage can clean, but that was our only minor complaint. Overall, loved the place and would consider staying here again!

Cottage rentals with a kayak

Top guest favorite
Cottage in Shelter Island
4.97 out of 5 average rating, 108 reviews

Shelter Island Waterfront Getaway

CindyRating, 5 stars6 months ago
Great stay, Maureen is very communicative and super helpful. Beautiful views
Top guest favorite
Cottage in Groton
4.96 out of 5 average rating, 317 reviews

Charming Historic Schoolhouse on Mystic River

KarenRating, 5 stars3 days ago
We had such a fantastic stay at this special home right on the river in lovely Mystic! It came stocked with everything we needed for a fun couple’s getaway. Gerard was so friendly and accommodating - we felt right at home. Can’t wait to return!
Top guest favorite
Cottage in Shelter Island
4.96 out of 5 average rating, 107 reviews

3 Bedroom Cottage Gem

MontagueRating, 5 stars1 week 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
Cottage in Guilford
4.99 out of 5 average rating, 103 reviews

Waterfront Joshua Cove Cottage with private beach.

KitRating, 5 stars3 days ago
A truly lovely spot! Quiet, relaxing and comfortable. We enjoyed the view of the water, reading on the patio in the lounge chairs and sitting on the bench overlooking the beach. We would love to come back again.
Top guest favorite
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!
Guest favorite
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
Cottage in Bethlehem
4.98 out of 5 average rating, 106 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AmyRating, 5 stars3 days ago
I wanted a weekend getaway for my son’s 13th birthday that landed on Friday the 13th, I came across this cabin airbnb and decided to book and give it a try. this location is an hour away from our home and gave us that peace of paradise we were looking for. the cabin felt like home and had everything you can possibly need. I honestly wish I can give higher than a 5 star because this cabin was perfect. I’ll be booking again for a winter weekend getaway. thank you for hosting my family and I.
Guest favorite
Cottage in Montville
4.95 out of 5 average rating, 106 reviews

Beautiful lakefront retreat just 15 mins to casino

NicoleRating, 5 stars3 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!

Cabin rentals with a kayak

Superhost
Cabin in Lebanon
4.88 out of 5 average rating, 17 reviews

Casa Lago

JasonRating, 5 stars3 weeks ago
A wonderful cozy little place to stay! We will definitely look you up again when we are back in the area!
Guest favorite
Cabin in North Stonington
4.93 out of 5 average rating, 42 reviews

Lakeside Landing

TabithaRating, 5 stars3 days ago
We stayed at Lakeside Landing with our 1 year old to enjoy Father’s Day weekend in the Mystic area. This place was perfect to enjoy a fire by the lake, watch the deer and other wildlife, and spend a few cozy evenings snuggled up in the living room. Everything was perfect!
Guest favorite
Cabin in Bethlehem
4.9 out of 5 average rating, 30 reviews

Swim, fish, kayak & RELAX!

GeraldRating, 5 stars3 weeks ago
We stayed for a graduation near by, it was perfect for we were looking for. I wish the weather would have been a bit warmer to enjoy the water.
Top guest favorite
Cabin in Bethlehem
4.95 out of 5 average rating, 82 reviews

Cabin by the lake I Private Beach I Paddle Board

AmyRating, 5 stars2 days ago
We loved our stay at Mariana’s cozy and comfortable cabin by the lake. The surroundings are beautiful, and the cabin is tastefully decorated and equipped with everything guests might need. Mariana was quick to respond to our questions, and made us feel very welcomed. The only disappointment was that it rained during our whole stay and we couldn’t enjoy the adorable deck off the side of the house - next time! We’re definitely happy we stayed here!
Guest favorite
Cabin in Coventry
4.88 out of 5 average rating, 136 reviews

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

MariaRating, 5 stars1 week 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.
Guest favorite
Cabin in Harwinton
4.85 out of 5 average rating, 13 reviews

Waterfront Cabin: Love Lake Life

JadeRating, 5 stars1 week ago
I would recommend this stay to anyone who needs getaway escape right on the lake as pictured!! It was a great family bonding trip We enjoyed it all Very close (10 min drive) to Torrington for groceries restaurants or any necessities or activities outside of cabin
Guest favorite
Cabin in New Hartford
4.98 out of 5 average rating, 50 reviews

West Hill Cabin

ChrisRating, 5 stars1 month ago
Great location near West Hill Lake and Brodie Park; walking distance to public beach, playground, and more. The house is very clean and well provisioned. A great stay!
Cabin in Stratford
4.81 out of 5 average rating, 44 reviews

Beautiful lakeside summer home

SondraRating, 5 stars10 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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