
Vacation rentals with a kayak in Portland
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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!

New Waterfront |Near the White Mountains |Firepit
Just got back from our weekend stay . Beautiful space that looked just like the photos. House was spotless. The house is located in a very peaceful and private area. Our family enjoyed the kayaks on the pond during the day and the fire pit on the deck at night . Very relaxing weekend .

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.

Luxury 6 bedroom Beach House 50 ft from beach
The house was beautiful and worked perfectly for our group! Check in was very easy, and the house was spotless when we arrived. My favorite part it was the yard - perfect for a big barbecue with a large group.

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.

Luxury Lakefront Paradise w/ Private Beach
An absolute gem! Incredible house in a gorgeous location… an ideal retreat!! Enjoyed a 5 day family reunion here and it was perfect…. Could spend time catching up, laughing with each other in common areas or while at other times, each could enjoy time in their own space. So many areas to use together or separately and so much to do on the property, or just a short drive to sights, amenities and shopping. Could easily have stayed longer and this would be fantastic for a couples getaway or a family vacation! Jason and Yvonne were so helpful and easy to communicate with, and we felt right at home from the time we made the booking. Truly a 5 star experience!! Thank you!

Secluded Lakehouse/2 private docks/Hottub/big yard
What a beautiful place. Chris and Erica have done a great job. Everything we needed and more. There was a problem with the hot tub and they where able to fix the problem and had it hot and ready for us when we where ready to use it. Amazing weekend catching up with the ladies. We will definitely come again.
Cottage rentals with a kayak

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug
My husband and I spent 6 days here for our anniversary. I wanted a location on the water and close to visit all the major coastal towns in Maine. This was perfect! The home, felt like home, and everything was clean and beautiful. Adam was very helpful whenever I had any questions. Sipping coffee every morning on the back porch and watching the sunrise over the lake was so peaceful. Grocery store close by and great hiking/walking areas right out the front door. Can’t wait to come back and bring the family.

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!

Coastal Waterfront Tiny home in West Bath
Had an amazing stay again at Jon’s place on the ocean. Beautiful area and host is very responsive. We will be back. Highly recommend!

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.

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

Private oceanfront cottage, great views, and float
the stay was nice, the place was clean, match the description, pretty easy to find, and Christine had great communication. very beautiful views, right on the water, kayaking was nice.

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.

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!!

Cozy Camp Round Pond - Kayak, Swim, Bonfire, Games
We had a great stay at Leah's cabin. The place was warm and cozy, and we enjoyed the lookout onto the beautiful frozen lake. Leah was very proactive and responsive. A great stay!

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

Lakeside Cabin Nestled in the Pines
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.

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.

Modern Cabin: View, Hot Tub, 10min Walk to Lake
Absoultely love the cabin. Truly a gem, with quite a bit of thought and time put into making it a great experience for all. I would highly recommend. Kris is also a great host - very responsive and he clearly cares a lot about the place and our enjoyment.
Quick stats about vacation rentals with a kayak in Portland
Total rentals
20 properties
Nightly prices starting at
G$20,982 GYD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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