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Holiday rentals with a kayak in Middlesex County

Find and book unique kayak rentals on Airbnb

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Popular amenities for kayak rentals in Middlesex County

House rentals with a kayak

Top guest favourite
Home in Old Saybrook
5 out of 5 average rating, 35 reviews

Romantic Couples Retreat with Private Sandy Beach

JazminRating, 5 stars5 days ago
Had such a lovely stay at this house! It’s super cozy, beautifully kept, and you can’t beat waking up right by the water. Everything was clean, comfortable, and felt really welcoming. The views were breathtaking — made the whole stay even more special. I couldn’t have asked for a better spot to relax and recharge. Would definitely love to come back!
Guest favourite
Home in Madison
5 out of 5 average rating, 17 reviews

Beach Home & Garden Paradise

BethanyRating, 5 stars4 days ago
We loved our stay at this beach house. The house was gorgeous, and we especially loved gathering around the huge island in the kitchen. My 5 year old son loved the beach which was just a stones throw away. Would definitely stay again!
Superhost
Home in East Hampton
4.75 out of 5 average rating, 28 reviews

Charming River Home

CourtneyRating, 5 stars4 months ago
This was a great location for our family of 7. There were enough beds, good amenities, and it was a great location to get down to the Connecticut River. It was centrally located and we were able to explore many cities in CT due to the location. The hosts were extremely responsive and the home was well-maintained.
Top guest favourite
Home in Old Saybrook
5 out of 5 average rating, 49 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

DavidRating, 5 stars1 month ago
What a beautiful place and conveniently located. The house was wonderful decorated, was very comfortable and definitely was a relaxing place to get away. Irina was a wonderful host and the home had many wonderful amenities to offer.
Superhost
Home in Clinton
4.71 out of 5 average rating, 90 reviews

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens

MaryRating, 5 stars4 days ago
This house was very good for me and my friends and we would love to go back!
Guest favourite
Home in Guilford
4.96 out of 5 average rating, 23 reviews

The Osprey Nest w/views of Long Island Sound

AlexRating, 5 stars3 months ago
This is a great place! I just finished my fourth visit (approaching 50 nights in this home) and I didn’t want to leave. Book this place if you want to wake up and drink coffee while watching sunrise in a second floor sun room or if you want a 1 mile walk to town (all sidewalks) and 200 meter walk to beach or if you want a place that’s stocked with kitchen utensils! I could go on and on. If it matters, it’s also not a corporate type Airbnb. Recommended!
Superhost
Home in Madison
4.89 out of 5 average rating, 44 reviews

Coastal getaway with water views in every room

KathyRating, 5 stars8 months ago
Meaghan’s place was everything we needed and more! Loved the views, the waves, the sea breeze, the bird observing, the walks to Grass Island, the together time with family in a quiet, secure & well appointed setting. Meaghan equipped us with everything! She was very responsive to answer questions. This is one of those treasured memories. Can’t wait until we get back again to this special location! Thank you!
Guest favourite
Home in East Hampton
4.9 out of 5 average rating, 39 reviews

Waterfront Lake House

ShannonRating, 5 stars3 weeks ago
Absolutely loved this location! The kitchen was perfect to cook our own dinner, and the dining room table is absolutely awesome. Love the chairs & bench, along with the view of the tv. Everything that was needed, was there. It was an awesome staycation. Thankyou so much!

Cottage rentals with a kayak

Guest favourite
Cottage in Branford
5 out of 5 average rating, 10 reviews

Beachfront Cottage Serene Private Beach, Kayaks

BasilRating, 5 stars8 months ago
We loved it. Redefines “fully stocked” - David’s place had everything we could ask for. The water at high tide was magical. Kayaking, fishing and we found over 100 (literally) hermit crabs.
Top guest favourite
Cottage in Shelter Island
4.97 out of 5 average rating, 107 reviews

Shelter Island Waterfront Getaway

ClaudiaRating, 5 stars5 months ago
We thoroughly enjoyed our stay. The location was beautiful and very peaceful.
Top guest favourite
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 favourite
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.
Top guest favourite
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 favourite
Cottage in Montville
4.95 out of 5 average rating, 102 reviews

Beautiful lakefront retreat just 15 mins to casino

JohnRating, 5 stars3 weeks ago
We had to come to the area for a family funeral, so this was a last minute booking, and Nicole was just the best. She got us in quickly, with less than 24 hours' notice. The house is absolutely beautiful, and overlooks the equally beautiful Oxoboxo Lake. Would recommend this house to anyone needing to stay in the area. Thank you Nicole!
Guest favourite
Cottage in Cutchogue
4.98 out of 5 average rating, 44 reviews

Stunning waterfront modern farmhouse with dock.

PatriciaRating, 5 stars1 month ago
Returning guest, we had a wonderful weekend at Michelle's idyllic home. Plenty of space for our two families and 3 kids. The kids love having their own space in the "she shed" while the adults enjoy the lakeside views from both the yard and inside the spacious living area. The house is always immaculately clean. Beds and other furnishings are comfortable, and the house is an easy drive to everything the North Fork has to offer. We look forward to returning (again!) soon.
Top guest favourite
Cottage in Old Lyme
4.98 out of 5 average rating, 42 reviews

Cottage with Roger’s Lake Views

GwenRating, 5 stars1 week ago
My family and I had a great stay here! The place was exactly as described—clean, cute, and super comfortable. The host was incredibly responsive and thoughtful, providing clear check-in instructions and help that made our trip seamless. The location was perfect—close to the lake in a quiet neighborhood. We especially appreciated the little touches like fresh towels, coffee, snacks, Wi-Fi, everything you could possible need for a long weekend. I’d absolutely stay here again and highly recommend it to anyone visiting the area!

Cabin rentals with a kayak

Guest favourite
Cabin in Coventry
4.88 out of 5 average rating, 130 reviews

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

EmilyRating, 5 stars1 week 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!
Guest favourite
Cabin in Harwinton
4.8 out of 5 average rating, 10 reviews

Waterfront Cabin: Love Lake Life

MichelleRating, 5 stars1 week ago
Nice little getaway spot. beautiful little lake.
Superhost
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 favourite
Cabin in New Hartford
4.98 out of 5 average rating, 50 reviews

West Hill Cabin

ChrisRating, 5 stars1 week 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!
Superhost
Cabin in Coventry
4.78 out of 5 average rating, 107 reviews

Lake - PetsOK - Wi-Fi- W&D - Fire Pit - Kayaks

HunterRating, 5 stars1 week ago
Joe was fantastic, very good with communication. The place was very tidy, well kept and had many thoughtful touches. We really appreciated the location as it was 10 minutes from just about anything you could need (very convenient) but was peaceful. Would definitely recommend Joe as a host and this location for a rental.
Superhost
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 favourite
Cabin in Coventry
4.85 out of 5 average rating, 167 reviews

Lake - PetsOK - Wi-Fi- W&D - Fire Pit - Kayaks

KyleRating, 5 stars3 days ago
As someone who travels quite often for work, I can confidently say that this property was in a beautiful location, looks exactly like it does in the photos, and is a fantastic value for what we had paid. It’s walking distance to the lake, kayaks, life vests, and kayak dolly’s are provided, so you do not need a vehicle to get the to the lake! The local restaurants are amazing and provide great service. The attention to detail to ensure a comfortable stay is unmatched. From the interior decorations, to the supplies that are stocked, we were quite impressed. Joe has ensured that you will be covered for anything you may have forgotten to pack. The neighborhood is extremely quiet and there is minimal light pollution in the area, so you can star gaze while you enjoy your time by the beautiful fire pit. Joe was also extremely communicative and made us feel like we had everything we needed to have a wonderful stay. I would highly recommend this location!

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