
Vacation rentals with a kayak in Scarborough
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House rentals with a kayak

Rising Tide Times - quintessential Maine cottage
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.

Little Sebago Lakefront Getaway
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!

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!

Waterfront on Bonny Eagle June July August weeks
My family was looking for a place this year to just get away, and Michael’s place was the perfect spot to do so. Close enough to the ocean and Portland, but far enough away to for some much needed R& R. Michael is an excellent host, and is very responsive to all messages. Thanks for everything!

Windham Wind Down-Lakefront, Dock, Kayaks, & SUPs
What a wonderful house! It would be a perfect family vacation spot to spend quality time together, fishing, kayaking, making s'mores, playing board games, or relaxing with some reading or television.

Kayak to the Causeway-50s cottage with modern vibe
This has been by far the nicest place we have stayed. Super clean and nicely decorated. Wonderful communication by the hosts. Perfect weekend getaway.

Lakehouse on Highland Lake
Beautiful place in great location. Did a weekend trip that included Portland based activities and a lake day at Lake Sebago. This was right in between making both super easy! The house was beautiful, clean, and slept everyone very comfortably. The view on the water is amazing, and Timissa was very responsive, accommodating, and kind!

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.
Cottage rentals with a kayak

Romantic waterfront cottage for two in Maine
We stayed at the cottage for a little celebratory getaway. Although the weather only partially complied, we were amazed by the beautiful views that surrounded the cottage. We spent some time exploring the area and there are some spectacular little gems hidden throughout and around Windham. Maryellen and Bryan were so sweet and made sure to make this stay feel a little closer to home. Definitely a “don’t miss” property!

Cozy camp near highland lake
Super cute little camp house good for a nice quiet trip. Didn’t get to trying the kayaks but the lake is nice and easy to access.

Cozy waterfront home on Merrymeeting Bay.
Loved our time here! It’s about a 40 minute drive from Portland and then 5-10 from Brunswick. The neighborhood is quiet and perfect, exactly what we needed to relax! We loved coming back from Portland and grabbing dinner and gelato in Brunswick, such a nice way to unwind from a long day. Highly recommend and would love to stay here again :)

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

Charming Designer Cottage on Marsh
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.

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.
Marina’s little cottage is a gem which we highly recommend. It is situated high above the peaceful and quaint lake providing interesting views. The sunrise while sitting on the dock was a favorite. A great place to get some reading done without everyday distractions. Everything was clean, neat and organized! The new kitchen was a treat! For a small place it is very spacious inside, beds and sitting areas comfy and everything one needs for a pleasant stay. Marina gets an A+ for communication. We may be back next year and will recommend it to friends and family. Please don’t hesitate to book this place for a relaxing getaway.

Riverpine Retreat - clean&bright waterfront home
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

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!!

Thompson Lake, No Cleaning Fee Pine Point Cottage,
wonderful birthday weekend stay. very clean, quiet and peaceful! we had everything we needed to stay busy in the rain! very responsive host

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

Get away at Crystal Lake
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!

Private cabin w hot tub,skiing,firepit & mountains
Alexa’s place was comfortable, well furnished, and impeccably clean, and she was extremely easy to get ahold of and communicate with! We had a fantastic two days away from home at this place.

Maine Lakes-Pleasant Mt-Private Trails
Lovely cabin in a beautiful location. Check in was easy and Jeff is a very responsive host. Highly recommend this spot.

Beautiful Log Cabin on Belleau Lake -2900 sqft!
Great place for a group to stay and enjoy the lake!

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.
Quick stats about vacation rentals with a kayak in Scarborough
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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