Holiday rentals with a kayak in Cumberland

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House rentals with a kayak

Superhost
Home in Harpswell
4.9 out of 5 average rating, 115 reviews

Rising Tide Times - quintessential Maine cottage

AnthonyRating, 5 stars8 months ago
Stayed at Bethany's place for a long weekend at the end of the season. The location is unbeatable, the house is situated on its own little peninsula in a stunning cove; it feels very private and has amazing views of the water. There's tons of outdoor space and seating, along with several kayaks. The house itself is clean, quiet, and peaceful, although it's definitely small--probably best for one or two people, or a couple with a small child. Access is down an unpaved road but Bethany's very clear instructions made it easy to find, and she was responsive to any questions we had. Harpswell abounds with areas to hike and explore, lots of good places to eat (though you will definitely need a car) and is less than an hour from Portland and only half an hour from Freeport.
Guest favourite
Home in Gray
4.97 out of 5 average rating, 33 reviews

Little Sebago Lakefront Getaway

DanielRating, 5 stars8 months ago
Violeta and her space were amazing. The house was exactly as advertised and we felt right at home for our long weekend. We are looking forward to making this a yearly visit!
Superhost
Home in Greenwood
4.96 out of 5 average rating, 111 reviews

Lakefront summer getaway cabin for 6

LezlieRating, 5 stars2 weeks ago
We had a great week at the cabin! The view is amazing and it was so relaxing. Courtney was very responsive and attentive. Highly recommend for a cozy getaway in a beautiful setting.
Guest favourite
Home in Windham
5 out of 5 average rating, 5 reviews

Windham Wind Down-Lakefront, Dock, Kayaks, & SUPs

CheriRating, 5 stars1 day ago
Our group was two small families with kids ages 6 and 8. Everyone had a great time. If you’re looking for a home to get out into nature, this is it. The private dock and lake gave us hours of time to play outside. Kayaks, paddle boards, and fishing off the dock was fun and all part of the house. Kids had a blast and so did the adults. Perfect for family summer vacation. We had a few rainy days but either played board games inside or went into Portland which is only 20-30 minutes away. Visited Mackworth Island in Casco Bay. Must do if you want to have a day excursion. The house well kept and easy to navigate. We spent more time outside on the lake than inside.
Guest favourite
Home in Wakefield
4.98 out of 5 average rating, 170 reviews

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

BinayRating, 5 starstoday
We had an absolutely wonderful time at Julie's lakeside home for Father’s Day weekend. The setting was serene, with beautiful views of the water, making it the perfect spot to relax and enjoy quality time together. The home was well-equipped and comfortable, offering everything we needed for a memorable stay. Julie was a fantastic host, ensuring that our experience was seamless and enjoyable. We truly appreciated the peaceful ambiance and thoughtful touches throughout the space. Highly recommend for anyone looking for a lakeside retreat!"
Guest favourite
Home in Naples
4.98 out of 5 average rating, 163 reviews

Kayak to the Causeway-50s cottage with modern vibe

SharonRating, 5 stars1 month ago
This has been by far the nicest place we have stayed. Super clean and nicely decorated. Wonderful communication by the hosts. Perfect weekend getaway.
Guest favourite
Home in Windham
4.96 out of 5 average rating, 45 reviews

Lakehouse on Highland Lake

SusanRating, 5 stars1 day ago
The house was prefect for our family, plenty of space. The house provided a number of great amenities from linens and towels to canoe and kayaks .We enjoyed sitting out on the deck overlooking the lake. If you enjoy fishing this lake is for you. Great location to restaurants, shopping and site seeing. Timissa was an attentive host, she answered all my questions and made my family feel very welcomed at her lake house. Thank you for all the wonderful memories.
Guest favourite
Home in Greene
4.89 out of 5 average rating, 79 reviews

Beautiful Maine Lakeside Cottage

KaeleeRating, 5 stars2 days ago
This was a wonderful stay! It was so cozy and peaceful. I wish I could have spent even more time in the cabin. Bethany was a wonderful host! Instructions were super clear and there were lots of activities and fun things to do!

Cottage rentals with a kayak

Guest favourite
Cottage in Conway
4.94 out of 5 average rating, 345 reviews

20ft from the Water with Mountain View!

AlisonRating, 5 stars1 week ago
Loved our stay at this peaceful lake. The house is perfect- cozy and has everything you need. We loved paddleboarding and the access to cute downtown North Conway is ideal!
Superhost
Cottage in Lyman
4.83 out of 5 average rating, 103 reviews

RK North : All season Waterfront cottage with dock

EricRating, 5 stars2 weeks ago
A Perfect Waterfront Escape – 5 Stars My wife and I had an unforgettable stay at RK North Waterfront Cottage. From the moment we arrived, we were welcomed by breathtaking views, fresh coastal air, and a sense of peaceful seclusion that made this trip truly special. The cottage itself was spotless, beautifully maintained, and tastefully decorated with cozy touches that made it feel like a true home away from home. We especially loved the spacious deck overlooking the water — perfect for morning coffee or evening wine while watching the sunset. The hosts were thoughtful and responsive, ensuring we had everything we needed without ever being intrusive. Whether it was relaxing by the fire pit, walking along the shore, or just enjoying the tranquility of the surroundings, every moment felt effortless and restorative. If you’re looking for a quiet getaway with charm, comfort, and stunning waterfront views, this is the place. We’re already planning our next visit. — Eric & Juliet DiNoto
Guest favourite
Cottage in Kennebunkport
4.98 out of 5 average rating, 109 reviews

Charming Designer Cottage on Marsh

RobinRating, 5 stars6 months ago
Tiny but beautiful cottage with walls of windows in the living room and bedroom overlooking the salt marsh. It was like staying on a boat! Great kitchen, comfortable bed and cozy fireplace. Beautiful in the winter.
Guest favourite
Cottage in Standish
4.92 out of 5 average rating, 119 reviews

Peaceful Lakeside Maine Retreat

TeaganRating, 5 stars2 weeks ago
Janet’s place in Standish was great and we could not have asked for a better host. Apart from the home itself, Janet was very friendly and responsive. She even proactively offered early check in / late check out, extremely unexpected and appreciated! Would absolutely recommend this BNB 10 times out of 10.
Guest favourite
Cottage in Livermore
4.95 out of 5 average rating, 150 reviews

Bass Point Lakeside Cottage: Livermore, Maine

BiancaRating, 5 stars7 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 favourite
Cottage in Middleton
4.97 out of 5 average rating, 152 reviews

Beautiful Lakeside Cottage

JonathanRating, 5 stars3 days ago
My wife and I wanted to have a lakeside getaway to kick off the summer! The weather was a bit colder than we had hoped, so we ended up enjoying the cottage to its fullest, which was a much needed and relaxing stay with everything we needed right there. It was very cozy and the lakeside view was wonderful, especially in the mornings. The owner was also very responsive to messages, making the experience seamless. We hope to visit again!
Superhost
Cottage in Freedom
4.79 out of 5 average rating, 483 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Leigh AnnRating, 5 stars3 weeks ago
Helen was actually wonderful. She returned calls and everything. It was a great place to stay beautiful and hope to stay there again someday.
Superhost
Cottage in Parsonsfield
4.87 out of 5 average rating, 158 reviews

Riverpine Retreat - clean&bright waterfront home

BellaRating, 5 stars1 month ago
This riverside retreat was the perfect weekend getaway! It was so peaceful and we felt right at home. It was a bit cozier than the pictures made it seem but it was perfect for two of us and a big dog. Everything was clean and it was easy to find things such as extra towels and plates. It was raining almost the whole weekend but there was still so much for us to do between games, the game shed, and the screened in portion of the shed where we could sit, watch the river, and listen to the rain. We hope to go back again someday!

Cabin rentals with a kayak

Guest favourite
Cabin in Woodstock
4.96 out of 5 average rating, 154 reviews

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub

JenavieveRating, 5 stars3 months ago
My friends and I had a great time relaxing at this beautiful place. Aqeel and Michelle were extremely responsive and helpful when necessary. We would stay again!
Top guest favourite
Cabin in Windham
4.92 out of 5 average rating, 205 reviews

Private Hilltop Cabin, Lakes and Trails Abound..

PeterRating, 5 stars8 months ago
We had the absolute best time at MJ’s place, highly recommend !! The house is spatious yet very cozy and quiet, with a nice back porch to sit and enjoy the surrounding woods! Home is also very close to town and to Poryland/coastline, and the cleanest lake to swim in that we’ve ever been to! MJ was very helpful and quick to respond. Stay here! We hope to return sometime soon!!
Guest favourite
Cabin in Waterford
4.94 out of 5 average rating, 159 reviews

Lakeside Cabin Nestled in the Pines

LindseyRating, 5 stars7 months ago
Beautiful place. Lovely decorated. I would say that it is probably a little expensive for staying there in the winter/ fall time. Only one of us could sit on the couch at a time due to its location by the tv. The shower is really small and there is no room for toiletries in the bathroom at all. There is a rack but I had to keep all my bathroom stuff in bags the entire time because it is just lacking in space. I would think The price is worth it if you’re staying there in the summer and get to use the lake.
Guest favourite
Cabin in Harrison
4.99 out of 5 average rating, 127 reviews

Get away at Crystal Lake

Natalia Wilkin Rating, 5 stars1 month ago
Wonderful Stay in a Great Location! Zak and Emily’s house was exactly as described. It has a fully equipped kitchen, a grill, and a fire pit outside, making it perfect for relaxing evenings. The house is stocked with towels and other essentials, so we had everything we needed. There’s also a ping pong table, which was a lot of fun, and a great collection of movies for entertainment. Check-in was super easy, and the house is conveniently located across from Crystal Lake, offering a peaceful and scenic setting. Communication with Zak and Emily was excellent—they responded quickly and were very accommodating. Overall, it was a fantastic experience, and I would highly recommend staying here for a peaceful getaway. Thanks again, Zak and Emily!
Guest favourite
Cabin in Madison
4.92 out of 5 average rating, 134 reviews

Bear Cabin

AllysiaRating, 5 stars6 days ago
This was the perfect location for my husband and in laws. It was so peaceful. Thank you for a beautiful place to vacation.
Guest favourite
Cabin in Georgetown
4.86 out of 5 average rating, 122 reviews

Cozy log cabin on private pond, near Reid St Park!

CindyRating, 5 stars1 week ago
When you are out exploring a new area, the perfect way to end each day is in a cozy, relaxing secluded cabin in the woods, and this is just what Destie and George provide at The Little River Retreat. Their cabin, with its wide, inviting front porch with a sunrise view of mist over the pond, is just the place for morning coffee. They have thought of everything in terms of stocking the cabin, including rainy day and evening entertainment for all ages. I definitely overpacked as so much was provided by them! It is so nice to go to a place where you can take a step back from daily life and it's stresses, and just relax. Thank you for 6 wonderful days.
Top guest favourite
Cabin in Whitefield
4.98 out of 5 average rating, 120 reviews

Roxie the Tiny Cabin on 100 acres

BriannaRating, 5 stars2 days ago
We stayed at the Roxie cabin. The cabin itself was wonderful. The cabin was well stocked with anything you may need from playing cards to bug spray. We threw axes then took one of the canoes out and enjoyed the peaceful pond. Pizza making was definitely a highlight of the evening. I’d definitely recommend staying.
Guest favourite
Cabin in Denmark
4.95 out of 5 average rating, 188 reviews

Maine Lakes-Pleasant Mt-Private Trails

BillRating, 5 starstoday
Third visit in three years for a weekend fishing getaway. Great location, beautiful property. Excellent hosts. Looking forward to a return visit.

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