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 stars4 weeks 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, 26 reviews

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

TanyiaRating, 5 stars3 days ago
I would like to stay Lisa’s property looked just like the pictures, but it was honestly even better! We have been to many nice Airbnbs but this was the nicest. It was the special touches that were so thoughtful….beautiful fresh roses in the kitchen and bathroom, battery candles that came on in the evening, muffins, snacks, dog treats, shower steamers. So very welcoming. We had such a relaxing few days. The home is extremely clean with very comfortable decor and bedding and lovely thick bath towels. The master bath is spa like. We enjoyed sitting out on the huge deck while my son was fishing right across the street. If we get back to the area, we would stay here again in a heartbeat. Thanks so much Lisa for having us.
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 Brookfield
4.98 out of 5 average rating, 148 reviews

Stay at Old Dorset Farm & create lifelong memories

KarenRating, 5 stars2 weeks ago
We had a wonderful stay. The home is beautiful, and the hosts were very thoughtful. The crib we requested for our 1-year-old was already set up when we arrived, complete with a soft blanket and pillow. There was plenty of firewood for cozy fires in both indoor fireplaces, and our kids loved making s’mores outside. Ninka was warm, responsive, and helpful throughout our stay.
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.
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, 20 reviews

Sky of Blue, Sea of Green

KaylaRating, 5 starstoday
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!
Top guest favorite
Home in Old Saybrook
5 out of 5 average rating, 52 reviews

Great Hammock Getaway | Beaches, Views & Hot Tub

JoanaRating, 5 stars4 weeks ago
We spent a few days at this amazing place and absolutely loved it! The house is cozy, very clean, well-organized, and beautifully decorated – great taste in every detail. We especially enjoyed the hot tub and the fireplace – perfect spots to relax. The location is also excellent. The host provides bikes, and we used them to explore the nearby beaches and ride around the town. It was exactly the peaceful and relaxing break we needed from our busy routine. We would definitely come back! ♥️

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, 316 reviews

Charming Historic Schoolhouse on Mystic River

DanRating, 5 stars2 weeks ago
We really enjoyed our stay in Mystic! The School House was cozy, charming, well-ventilated with great A/C, clean, and very welcoming. The kitchen was well-equipped and easy to cook in, which made meals at home a breeze. Gerard was an exceptional host — proactive, thoughtful, and always made sure we had everything we needed. We also lucked out with friendly neighbors in the Captain’s House next door. The outdoor space was a real highlight, with beautiful views of the Mystic River right from the doorstep. If you don’t mind a bit of limited headroom in the attic bedroom, this BnB is an easy recommendation!
Top guest favorite
Cottage in Shelter Island
4.96 out of 5 average rating, 107 reviews

3 Bedroom Cottage Gem

MontagueRating, 5 stars6 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
Cottage in Guilford
4.99 out of 5 average rating, 102 reviews

Waterfront Joshua Cove Cottage with private beach.

ConnorRating, 5 stars2 weeks ago
Our 2 day stay at the cottage was just what we’d hoped for our wedding weekend! Annalisa was so responsive and accommodating. A wonderful host, such wonderful hospitality and an amazingly stunning private retreat! Would definitely return!
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 East Haddam
4.9 out of 5 average rating, 131 reviews

Direct Waterfront Cottage on Moodus Reservoir.

WendyRating, 5 stars2 weeks ago
Nice little spot with boats on the pond. Went there for my son’s Wesleyan graduation and could take family out on the kayaks.
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, 105 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AlexRating, 5 stars2 weeks ago
great time as always!

Cabin rentals with a kayak

Top guest favorite
Cabin in New Milford
5 out of 5 average rating, 8 reviews

Lakefront cabin with private dock on stunning cove

AlekseyRating, 5 stars9 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!
Superhost
Cabin in Lebanon
4.88 out of 5 average rating, 17 reviews

Casa Lago

NafisRating, 5 stars1 month 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
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
Cabin in North Stonington
4.93 out of 5 average rating, 41 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
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!
Guest favorite
Cabin in Bethlehem
4.9 out of 5 average rating, 30 reviews

Swim, fish, kayak & RELAX!

GeraldRating, 5 stars2 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, 80 reviews

Cabin by the lake I Private Beach I Paddle Board

SusanRating, 5 stars1 day ago
Thank you Mariana for allowing me to stay in your beautiful cottage. I needed to step away from my life for a few days and this was the perfect place. Quiet, private, just lovely interior. Decor is incredibly soothing, I’ve never stayed in an Airbnb or any rental that had thought of so many details. Anything you needed, anything you forgot to bring it was here. One of my favorite places I’ve ever stayed, actually teared up in gratitude as I left which I’ve never done!! Thank you so much
Top guest favorite
Cabin in Voluntown
4.95 out of 5 average rating, 743 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

ChristineRating, 5 stars2 days ago
Great camp and peaceful area. Angela is a great host and very accommodating. I have stayed twice and would definitely come back again.

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