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 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 stars3 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 Old Lyme
5 out of 5 average rating, 21 reviews

Sky of Blue, Sea of Green

KaylaRating, 5 stars2 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!
Top guest favorite
Home in Old Saybrook
4.97 out of 5 average rating, 124 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

MaryRating, 5 stars3 weeks ago
Laurie was an amazing host, very responsive! We wanted to bring our dog with us for the weekend and the fenced in yard added to the great experience! The place is much larger than the photos with plenty of living room space for the family. The kitchen was well equipped, with everything needed! We appreciated her hospitality and friendliness and would definitely stay again!
Top guest favorite
Home in East Hampton
4.99 out of 5 average rating, 72 reviews

Lake Fun: PingPong, Pool Table, Slide, EV Charger

KylieRating, 5 stars1 week ago
We had a wonderful stay at this gorgeous lakehouse! Honestly, the pictures don't do the place justice. The lake was lovely, and the house was well-equipped and spotlessly clean. The furnishings and decorations were far nicer than you often find in an airbnb; it felt like a true home. Everything we could have possibly needed to enjoy the lake was provided, from canoes and kayaks to inner tubes, and the kitchen was well-equipped with all manner of cooking utensils and basic spices/condiments. Linda and Dick were great--very communicative and easy to get ahold of, but left us to our privacy otherwise. Would absolutely go back again!
Guest favorite
Home in Exeter
4.97 out of 5 average rating, 125 reviews

Come relax at Lakeside Landing

JamesRating, 5 stars1 day ago
This stay was for a family gathering as my daughter graduated from North Kingstown on Thrusday. Tonya was an amazing hostess and the home was more than what we anticipated. we will most definitely utilize her home every time we visit! LOVE YOUR JOURNEY!
Top guest favorite
Home in Old Saybrook
5 out of 5 average rating, 52 reviews

Great Hammock Getaway | Beaches, Views & Hot Tub

Carl And AnneRating, 5 starstoday
This was our second stay at this lovely home. It was the perfect place to spend a week celebrating our 51st anniversary! The house itself is beautifully decorated, impeccably clean, and offers everything we could need for cooking, comfort, and leisure. We especially enjoyed the gas fireplace and the hot tub! We made good use of the local beach pass that was furnished for us. The two very close by beaches were well-maintained and very enjoyable. We would highly recommend this location and plan to make this our go to Airbnb when we are in this area. Irina is the perfect host! She is extremely responsive and reliable.
Guest favorite
Home in Wading River
5 out of 5 average rating, 17 reviews

Hang by the (Chel)SEA

JillRating, 5 stars2 weeks ago
Spent to my birthday here with my husband, dogs and toddler. Had my gender reveal birthday cake, outback under the sunset. Truly magical.✨ The backyard was ideal. Was able to tie the dogs to the deck with a 20 foot leash. It kept them contained to the backyard & away from beach goers on foot and other dogs. The dunes kept the backyard private you’re not staring at your neighbors. Felt so secluded. I also have some mobility issues and you couldn’t ask for an easier way to enjoy the beach & get your toes in the sand. The house & deck are spacious and easy to navigate with a walker. Was able to add extra days to our stay. Would 100% stay here again.

Cottage rentals with a kayak

Guest favorite
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

JenRating, 5 stars2 weeks ago
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!
Top guest favorite
Cottage in Groton
4.96 out of 5 average rating, 317 reviews

Charming Historic Schoolhouse on Mystic River

KarenRating, 5 stars1 day 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 stars1 day 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 Bethlehem
4.98 out of 5 average rating, 106 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AmyRating, 5 stars1 day 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!
Top guest favorite
Cottage in Thompson
4.99 out of 5 average rating, 140 reviews

Waterfront Cottage in Thompson CT • Dogs Welcome

JoeRating, 5 stars4 weeks ago
5 stars ⭐⭐⭐⭐⭐ We absolutely loved our stay at the Cottage on the Lake in Thompson, Connecticut! The home is charming, beautiful, and immaculately kept—the perfect peaceful getaway. Jan, the host, went above and beyond to make sure we were comfortable from start to finish. She checked in with us multiple times during our stay to ensure we had everything we needed, and her kindness and attentiveness made us feel genuinely cared for. We felt so at home here. The neighborhood was just as welcoming—we even got to know the friendly neighbors and their adorable dog, Gigi, next door! This cottage has quickly become a favorite of ours, and we’re already looking forward to making it one of our regular Airbnb stays for years to come. Thank you, Jan, for such a wonderful experience!

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 North Stonington
4.93 out of 5 average rating, 42 reviews

Lakeside Landing

TabithaRating, 5 stars1 day 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 Foster
4.95 out of 5 average rating, 40 reviews

Secluded Lake House

JulieRating, 5 stars4 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 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, 80 reviews

Cabin by the lake I Private Beach I Paddle Board

SusanRating, 5 stars3 days 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 stars4 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.
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

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