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Vacation rentals with a kayak in Messalonskee Lake

Find and book unique kayak rentals on Airbnb

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Popular amenities for Messalonskee Lake kayak rentals

House rentals with a kayak

Guest favorite
Home in Newport
4.93 out of 5 average rating, 122 reviews

Sugarmaple Lakehouse - Sebasticook Lake Newport ME

SoniaRating, 5 stars3 months ago
We walked in and the Christmas tree lights were on and Christmas music was playing. It was lovely. It's a beautiful home and very cozy. Having a bedroom and full bath downstairs makes a difference for many of us (young and older) who may have trouble navigating the stairs to the second floor. This location is nice and quiet yet close to all the essentials. I spoke with Dottie before our stay and she was very nice, helpful, and informative. Thank you again Dottie! We look forward to staying again in the summer. Highly recommended!! Thank you Dave and Dottie!
Top guest favorite
A vibrant blue kayak is positioned in the foreground, with a wide view of Pleasant Pond stretching into the distance. Calm water reflects the sky above, while lush greenery lines the shores. Cloudy skies create a serene atmosphere perfect for relaxation and exploration.
Home in Gardiner
4.98 out of 5 average rating, 45 reviews

2 Acre Waterfront w/Canoes & Kayaks, Game Room

LivRating, 5 stars1 month ago
I love coming to Maine, and this was my first time staying at Rob's place—it was beautiful! Rob was more than accommodating and incredibly hospitable. The home is gorgeous, super clean, cozy, and very private. The game room was such a fun bonus! It was the perfect little getaway. Thank you so much, Rob, for everything! I will definitely be keeping this place in mind for future visits!
Guest favorite
Home in Fayette
4.9 out of 5 average rating, 21 reviews

Lakehouse with 100ft of private waterfront

GeorgeRating, 5 stars6 months ago
My wife and I spent our first year anniversary in this wonderful home. We had a great time enjoying the fall colors and over looking the beautiful pond, especially in the morning as the fog broke. Within 15 minutes there were several grocery shopping options, restaurants, and breweries. Perfect balance of being in a quiet setting but having amenities nearby. Would recommend and hope to go back next autumn!
Guest favorite
The exterior of a brown wooden house is showcased, with a constructed ramp leading up to a spacious deck. Surrounding trees display hints of autumn foliage, and a clear sky is visible in the background. The scene indicates a peaceful, natural setting near the lake.
Home in Newport
4.9 out of 5 average rating, 52 reviews

Our "CampUpta" on Lake Sebasticook

EphraimRating, 5 stars3 days ago
Nice lake front property. We would stay here again.
Top guest favorite
A calm river reflects the surrounding greenery, bordered by a well-maintained lawn. A wooden wharf extends towards the water, providing a peaceful place to sit and enjoy the view. A hint of colorful buildings can be seen in the distance, framed by trees.
Home in Pittston
4.99 out of 5 average rating, 144 reviews

Riverside

BradleyRating, 5 stars2 months ago
We had an amazing time over valentines day weekend. There was a snow storm and Kent snow blowed around our vehicle to make sure we could get out. The house is very comfortable and peaceful, amazing view of the river and just off the road enough to not be bothered by passing traffic. Definitely recommend!!!!
Guest favorite
Home in Palermo
5 out of 5 average rating, 9 reviews

Serenity on Sheepscot Lake

AshleyRating, 5 stars2 months ago
Our group of friends and family really enjoyed staying at this peaceful winter getaway house! We are already talking about coming back up in the summertime. The toys and games made my kids so happy and kept them well-entertained. Perfect amount of space for our big group! Lori was flexible and responsive, a wonderful host! Thank you again 🛷
Guest favorite
A serene waterfront scene showcases a calm lake surrounded by lush greenery. A small boat rests on a grassy area, inviting relaxation and exploration. The cloudy sky reflects over the water, creating a peaceful atmosphere.
Home in West Gardiner
4.96 out of 5 average rating, 26 reviews

2 BR Waterfront house with stunning view.

KristenRating, 5 stars6 months ago
This was a really nice house on a beautiful lake. The beds were comfortable and there were enough to accommodate us. It was very clean and easy to enjoy your stay. We really enjoyed our stay.
Superhost
A quaint wooden home is nestled among tall trees, surrounded by a mix of greenery, creating a natural setting. Sunlight filters through the branches, illuminating portions of the rustic exterior, which features a sloped roof and inviting porch.
Home in Liberty
4.8 out of 5 average rating, 5 reviews

Waterfront Home fully equipped

Mattie RoseRating, 5 stars7 months ago
Leslie’s home is exactly that, cozy, spacious, beautiful, peaceful, but above all it feels like a real home. Leslie was welcoming and gracious, she went above and beyond, I would certainly consider her a friend after staying there. I highly recommend this spot!

Cottage rentals with a kayak

Guest favorite
The view of the cottage is surrounded by lush greenery and mature trees, providing a serene outdoor space. The lake is visible in the background, with a fire pit and picnic table defined among the trees, creating an inviting area for relaxation.
Cottage in Manchester
4.89 out of 5 average rating, 27 reviews

Lakefront cozy cottages w/ dock, canoe & fire-pit!

JosephRating, 5 stars8 months ago
We absolutely love staying here! We come back year after year and love the cozy Maine cottage feel to this place. The perfect relaxing vacation and will definitely return for more!!
Guest favorite
A cozy cabin is nestled among towering trees, surrounded by a natural landscape. A gravel path leads to the entrance, where wooden steps are visible. The warm exterior contrasts gently with the cool tones of the forest.
Cottage in St. George
4.96 out of 5 average rating, 227 reviews

Hidden Haven A Rustic Retreat In St. George, Maine

LydiaRating, 5 stars2 weeks ago
Beautiful cabin in quiet and peaceful surroundings. Closes to attractions and multiple small towns with things to see and discover. Michelle and Dan were great hosts, everything we needed was in the cabin! They had a book of area things to do. They answered right away when we texted. I would definitely recommend their place!
Guest favorite
A serene lakeside setting features three green adirondack chairs arranged around a stone fire pit. The clear waters of Great Pond reflect the blue sky, while a wooden dock extends into the lake, bordered by lush green trees in the background.
Cottage in Belgrade
4.93 out of 5 average rating, 134 reviews

Near Waterville | Lake Great Pond | Dog Friendly

JennyRating, 5 stars1 month ago
We had a wonderful stay with our family and we were happy our dogs were welcome to come with us.
Guest favorite
A quaint cottage is nestled among vibrant gardens filled with colorful flowers, overlooking Snow Pond. A picnic table is shaded by a large umbrella near the water's edge, while trees provide dappled sunlight on the cottage's exterior.
Cottage in Sidney
4.91 out of 5 average rating, 130 reviews

Waterfront Cottage

AaronRating, 5 stars6 months ago
Amazing place, it was exactly what we needed.
Superhost
A wooden dock extends over calm water, leading to a small boat tethered at the side. Lush greenery borders the opposite shore, with a clear sky overhead, dotted with soft clouds.
Cottage in Livermore
4.94 out of 5 average rating, 53 reviews

Loons Rest- Maine Quintessential Cottage

CraigRating, 5 stars7 months ago
Loons Rest was the perfect get away spot for our 40th anniversary. We were lucky to enjoy the swimming dock in mid September as the daytime temperatures were in the upper 70's to low 80's. The lake was pristine and was warm enough for swimming still. We enjoyed watching and hearing the loons as well as the eagles and kingfishers. We loved the outdoor fire pit when the evenings turned cool as well as the indoor fireplace which is a work of art! Also the was plenty of well seasoned firewood. Everything about this place is very well thought out. If they don't have it you don't need it! The kitchen was well equipped and we were happy to find that there was everything we needed to prepare pizzas to cook on our solo stove pizza oven that we had brought along! John is a great host and responded quickly to any questions we had. Would highly recommend Loons Rest to anyone who is looking for a peaceful and relaxing spot to vacation.
Guest favorite
A serene view of a calm lake reflects the surrounding greenery and a rustic cottage nestled among the trees. A kayak paddle is partially visible in the foreground, indicating a peaceful outing on the water.
Cottage in Sumner
4.95 out of 5 average rating, 19 reviews

Peace at the Pond with Hot Tub & Sauna

JimRating, 5 stars6 months ago
Wonderful,private, well equipped cottage on pretty pond. Owners quick to respond to our texts. Relaxing hot tub and fantastic sauna! Many restaurants and breweries within a 30 minute drive. Book it ..... you won't wanna leave!
Guest favorite
The cottage is situated among trees on the water's edge, showcasing a modern design with large windows. A sloped bank leads down to the lake, where the reflection of the building and surrounding greenery can be seen on the water's surface.
Cottage in Livermore
4.95 out of 5 average rating, 149 reviews

Bass Point Lakeside Cottage: Livermore, Maine

BiancaRating, 5 stars6 months ago
I had a wonderful 4 night stay at the lake house and couldn't have asked for a better place to spend the little getaway. It is beautifully located on the lake and has this huge window in the living room from which you have an amazing view. The house has everything you need, even washing machine and dryer in the basement. I would 100% recommend this unique place! Christine has been super helpful throughout my stay.
Top guest favorite
The cottage features a screened-in porch that provides a comfortable outdoor sitting area. The front is accented by large windows, allowing natural light to fill the space. Surrounding vegetation creates a serene setting, with autumn leaves visible in the background.
Cottage in Rome
5 out of 5 average rating, 38 reviews

Cottage on Long Pond in Belgrade Lakes, Maine.

CatherineRating, 5 stars2 months ago
Our second time staying. Beautiful location, close access to the water. Thoughtful features inside. For wintertime stay the driveway was clear and we were able to keep very warm in the cabin, even on the coldest of days!! Tara is a responsive, kind and helpful host. Would definitely visit again!

Cabin rentals with a kayak

Top guest favorite
A kayak is stored on a wooden rack, positioned under a canopy of trees. Sunlight filters through the leaves, casting dappled shadows on the ground. The view of the river, partially obscured by vegetation, can be seen in the background.
Cabin in Dresden
4.95 out of 5 average rating, 184 reviews

McKeen's Riverside Retreat

BettyRating, 5 stars2 months ago
The cabin was just as advertised. A quiet clean space!!
Top guest favorite
Three individuals kayak along a calm river surrounded by dense woods. Canoes are gently paddled, while a motorboat is visible in the background. The atmosphere reflects a peaceful day on the water, with clear skies and greenery lining the shore.
Cabin in Dresden
4.98 out of 5 average rating, 240 reviews

Merrymeeting Midcoast Cabin

LenaRating, 5 stars4 months ago
Terrill and Charlie‘s cabin is lovely! Great communication, the cabin is well equipped (including lots of board games) and super cozy. We had a really relaxing time and might come back in spring :)
Guest favorite
The rustic cabin is nestled among towering trees, featuring a stone chimney and a wooden deck adorned with green chairs. A covered porch offers protection from the elements, while the natural surroundings create a serene atmosphere.
Cabin in China
4.89 out of 5 average rating, 171 reviews

Rustic Family Cabin on China Lake

JackieRating, 5 stars7 months ago
I loved this place! Enjoying coffee and meals outside on the deck overlooking the lake and beautiful surroundings of nature. I felt safe there and was a charming neighborhood. I loved that there were boats to use and a dock to watch sunset an autumn harvest moon over lake! Jess was the perfect host and made sure everything was great when I arrived. She was very helpful when I had any questions and I am looking so forward to going back there again! Thank you Jess for sharing this wonderful place!!!
Guest favorite
Cabin in Hope
4.97 out of 5 average rating, 101 reviews

Hobb’s House - Year Round Log Cabin on the Water

MelissaRating, 5 stars3 days ago
Connor was an AMAZING host! From the very beginning, he was always very responsive, and was consistently available to answer my questions promptly. His cabin on the lake was so cozy, it truly felt like our home away from home. It was beautifully decorated, peaceful, serene, well-stocked with anything that one could need. His recommendations were extensive and were very much appreciated. We were celebrating our 30th wedding anniversary and really loved being able to stay there with friends for a few days before departing for another excursion. It gave us time to celebrate and make some great memories with them - something that we will always treasure! The worst thing about this cabin? - Having to leave it in the rearview mirror! Connor, thanks so much for sharing your beautiful cabin with us. You can count on us to be back in the future! Thank you!
Top guest favorite
A private dock extends over calm waters, surrounded by vibrant autumn foliage. A flag is displayed proudly atop the dock, which features a ladder for easy access to the lake. Reflections of trees are visible on the water's surface.
Cabin in Oxford
4.94 out of 5 average rating, 130 reviews

Thompson Lake, No Cleaning Fee Pine Point Cottage,

ShelbyRating, 5 stars1 month ago
The cabin was very quaint and cozy for a snowy day. A quick walk to the lake and not too far from some cute shops and restaurants in Norway. Very responsive and friendly hosts. Incredibly clean and well maintained. Would stay again!
Superhost
A blue kayak is positioned alongside the cabin's exterior, with paddles resting above it. Various life jackets are hung nearby, showcasing bright colors. The surroundings are shaded by tall trees, creating a natural setting for outdoor activities.
Cabin in Raymond
4.93 out of 5 average rating, 154 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

WaltRating, 5 stars6 months ago
Came for the Fall colors; left in love with the place! Small but delightful. Cluttered in the most fantastical way. Nestled in paradise. Bonnie is so nice and friendly! Pay attention to the fact that the toilet is not attached to house. Short walk to privet and very clean!
Guest favorite
Cabin in New Vineyard
4.91 out of 5 average rating, 111 reviews

Mill Pond Waterfront Cabin On The Way To Sugarloaf

AdamRating, 5 stars3 weeks ago
4 of us stayed at this cute little cabin. Exactly as depicted and many helpful amenities were left for us to use such as seasonings, ice, and some wood. Pretty and quiet place to get away.
Top guest favorite
A handcrafted log cabin is set among tall trees, featuring a bright orange exterior and green trim. A screened porch offers a view of the nearby water. A sandy area in front of the cabin provides outdoor space for leisure, blending naturally with the surrounding landscape.
Cabin in Weld
4.94 out of 5 average rating, 108 reviews

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

RonniRating, 5 stars6 months ago
We celebrated our 25th wedding anniversary at this charming camp on Webb Lake, and it was everything we hoped for and more. The serene setting was perfect for enjoying the outdoors together. We spent our time fishing on the beautiful lake, where we caught a handful of fish. Kayaking was a highlight as well; the combination of being on the lake, mountain views and beautiful weather was simply magical. The camp itself was cozy and well-equipped, providing a wonderful weekend getaway. If you're looking for a peaceful getaway filled with outdoor fall activities, this is the place to be. We left already planning out next trip back. Thank you for sharing your home.

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