
Holiday rentals with a kayak in Cumberland County
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Top-rated Accommodation with a Kayak in Cumberland County
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Holiday House Rentals with a Kayak

The Sunrise House
Such a beautiful and peaceful place!! my kids didn’t want to leave! Lovely cottage feel with a beautiful view to the lake. We had such a great time taking the kayaks and paddleboard out on the water and enjoying our coffee overlooking the water from the sunroom,. Thank you for the great family memories!

Stunning Bridgton Lake House with EV charger
Beautiful and comfortable house in a lovely natural setting, five minutes from Pleasant Mountain, which we think is a wonderful family ski area. Marty was very kind and extremely helpful with all our questions and requests. We would love to return and experience other seasons here as well.

Lakehouse on Highland Lake
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.

Trickey Moose Family Retreat | Firepit Kayaks
We booked Trickey Moose to spend quality time with our two Maine teen grandchildren while they were on spring break. The place was perfect for our needs. The home is quite spacious yet offered each of us an element of privacy. We found the home in immaculate condition and stocked with every essential needed. The “community pantry” was a pleasant surprise and was stocked with the few incidental items we hadn’t brought along. The ping pong and air hockey tables created a friendly competition between the grandkids and grandparents. Great memories were made…. only wish we could have stayed longer.

Cottage on Pickerel Pond
We had a great time. Got to kayak around the pond several times. The jet skis and other motor boats and the gravel place were a little loud at times. That was my only complaint.

Modern Maine Lake House near Portland
Had a small bachelorette party here for one of my closest friends. It was the perfect place for a more relaxed girls trip but close enough to get to downtown Portland for any shops, sightseeing, and food! Highly recommended.

Secluded Lakehouse/2 private docks/Hottub/big yard
We enjoyed our stay at this beautiful home. Lots of amenities and the hosts are very friendly and quick to respond to any questions. It was roomy for our family of 5 and the beds were really comfortable. I’d say it easily accommodates 6-7 people. If you are adventurous and don’t mind sleeping in a small loft or a basement setting you could fit 10-11.

Charming 4 bedroom lake front, with private beach
We loved this home! It was apparent that the house had been updated indoors with a fresh look, refreshed paint, new floors, new appliances . The outdoor canoes, paddle boats, paddle boards were enjoyed by all. If I could rate this location with a 10, I would. Kudos to this location and to Patricia as a host for an immensely enjoyable experience. This is a definite return location!
Cottages with a kayak

Tranquil waterfront cottage
This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug
Great cottage right on the lake! Kayaks were great to take out and explore the lake and see wildlife as well. The cottage is spacious and comfortable. The kitchen is large and well appointed for any cooking you may want to do. Grill and plenty of beach chair/ towels available as well. Adam is extremely responsive and I highly recommend. The place is quite peaceful though the lake gets pretty busy on the weekends with boats but not in an obnoxious way. Loved sipping coffee and reading on the dock each morning. Will definitely book again!

Lake Front Cabin on Desirable Highland Lake
My wife and I stayed at John's place for a quick weekend trip but the house is large enough for several more with 5 additional beds plus some space in the living room for sleeping. Great location on the lake with amazing views and only about a mile and a half from downtown Bridgton with some shops and nice restaurants. The house was immaculate and had everything you need from kitchen accessories to towels to plenty of games and books. John was extremely responsive and I don't think I waited more than 30 minutes for the few back and forth messages we had. Definitely recommend!

Romantic waterfront cottage for two in Maine
Perfect place to get away and relax. We enjoyed fishing in the morning and evening and sight seeing during the day. Quick trips into Portland, Kennebunkport, Freeport, and the Maine Botanical Gardens (highly recommended ). Locally we enjoyed the Maine Wildlife Park and u-pick strawberries. Picked up some wonderful seafood at Bob’s in Windham to cook in the well supplied kitchen. Mary Ellen and Brian have thought of the many little things that make the cottage a hospitable place. They answered our questions promptly leading up to our trip.

RK North : All season Waterfront cottage with dock
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

Waterfront Getaway w/ Private Sandy Beach
Perfect for what we needed for a weekend getaway. So peaceful and a lot of interesting wildlife. We saw so many different types of birds! The hot tub is spacious and easy to use.

Peaceful Lakeside Maine Retreat
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.

Quintessential Maine Lakefront Cottage
We were looking for a quiet place near the water to relax and unwind. Marina's place was perfect! We enjoyed kayaking, and great views of the lake whether reading on the deck or playing boardgames in the dining room on a rainy day. We'd definitely stay here again.
Cabin rentals with a kayak

Private Hilltop Cabin, Lakes and Trails Abound..
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!!

Summah Getaway Lakefront Cabin w/Private Beach!
Beautiful and tranquil lake. Clean and comfortable cabin. Very welcoming host! Would absolutely recommend!

Lakeside Cabin Nestled in the Pines
We had a wonderful stay at Ricky’s cabin on Bear Pond! It was peaceful, with beautiful views of the water, and we loved having campfires in the evenings. The cabin was clean, cozy, and had everything we needed for a relaxing getaway in the Maine woods! Ricky was a great host—friendly, responsive, and made sure we felt right at home. We would highly recommend staying here!

Get away at Crystal Lake
Had an amazing stay here, so wondering could go fishing at the dock, the basement was so fun to play pong and just hang out, loved being able to watch disney+, just overall a wonderful stay and amazing and friendly people.

Private cabin w hot tub,skiing,firepit & mountains
We absolutely loved our stay at Alexa’s cabin. We enjoyed the hot tub, fully stocked kitchen, and truly felt like we could disconnect from the world to connect with those around us. Alexa was a great communicator, provided detailed instructions and local recommendations that were spot on. Don’t hesitate to book this Bridgton escape!

Charming log cabin on Crooked River in Maine
We loved our stay, the cabin was exactly what we were looking for: private, quiet and an escape from work demands. We especially enjoyed the outdoor space and close proximity to the river, and the screened in porch was simply wonderful to relax and read in. We would love to visit the area again.

Maine Lakes-Pleasant Mt-Private Trails
Third visit in three years for a weekend fishing getaway. Great location, beautiful property. Excellent hosts. Looking forward to a return visit.

Lake Front with Private Dock - BRAND NEW Furniture
This is an absolute beautiful place to stay. There is no question, I would 100% stay here again. My family had an amazing time here. Darryl was very easy to communicate with and made the stay very easy. If you’re looking for a clean and quiet place to stay, look no further.
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Story Land
- Popham Beach State Park
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- Surfside Beach
- Long Sands Beach
- Attitash Mountain Resort
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- Fox Ridge Golf Club
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- Brunswick Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
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- Purity Spring Resort
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