
Holiday rentals with a kayak in Portland
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Top-rated rentals with kayak in Portland
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House rentals with a kayak

Sebago Lake, ME *Lakeside*Hot Tub* just renovated
Our stay at Smith Cottage was quiet and peaceful. The home was bright and clean. We loved having the options of board games, foosball, cornhole and the hot tub to keep us entertained. The deck was a great gathering space with umbrellas for shade but plenty of sun hitting it for warmth! The gazebo was another favorite for night time gatherings. Colleen and Leo were responsive to our needs and all was as described in the listing. Everything was explained in the house guide, and if we had questions, they never made us feel like we were bothering them. They even recommended local attractions ahead of time so I could book a fishing tour. Definitely happy with our experience on the water using Burnt Meadow Guide Service. Also, being just down the road, Jordan's store made it easy if we forgot anything or needed fishing licenses. We look forward to booking again!

Open concept 4 bedroom Lakehouse
Great winter weekend stay in Maine, the house was very cozy and perfect for our group. The location is perfect for access to the ski mountains and the town as well. Overall highly recommend Roman’s place, I’m sure it is just as beautiful in the summer!

In the Trees - NH w/ Lake Access
We had a wonderful stay at this cozy, comfortable, and peaceful home—perfect for our family of five! The space was quiet, private, and truly felt like a home away from home. It's in a beautiful location right by Lake Province, and we had almost everything we needed for our 3-night Easter weekend stay. Our older children attend UNH, and this was the perfect spot for us all to be together, relax, play games, and enjoy quality family time. We love to cook, and the brand new kitchen was gorgeous and a joy to use—we prepared three amazing meals together! Just a heads-up for fellow cooks: the kitchen is stocked with the basics, so if you're planning more elaborate meals, you might want to bring a few extra tools. The outdoor space was also a highlight! With beautiful weather all three days, we spent a lot of time outside enjoying the fire pit, string lights, grilling, eating al fresco, and just being together. We truly loved our stay and are already looking forward to coming back.

Peaceful 4 bedroom lakehouse retreat
We had a fantastic time staying at Justin’s home!

2 BR Waterfront house with stunning view.
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.

Waterfront Condo- Maine village retreat
We had a great stay! Loved the views and hot tub. It was so close to town but felt private with the privacy fence. Owners were very responsive! Thanks for a great stay

Peaceful River House - 20 minutes from Portland!
We loved our stay at Wendy's place. The location is perfect on the river & close to Portland so it was the best of both worlds. Wendy couldn't have been any more accommodating, offering us early check in and a late check out. She was easy to communicate with & ensured we had a seamless experience. The house was exactly what we were looking for. We hope to visit again in the summertime!!!

Lakefront Retreat! Dog Friendly!
This lake house was beautiful and the view is stunning! Every room is well appointed and perfect for setting a lake vacation vibe. The house has everything you could need. The description and pics on Airbnb are thorough and completely accurate. Jenna was an awesome host - very responsive and helpful and flexible. We will definitely be back!
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.

RK North : All season Waterfront cottage with dock
It was overall a tremendous experience. I would definitely recommend it!

Private oceanfront cottage, great views, and float
Such a beautiful spot--Christine's house has gorgeous views, a dock and many kayaks. We enjoyed our stay--sitting on the deck, seeing the Northern Lights (!!)--thank you Christine for the heads up! Harpswell is a special place and this beach cottage is special as well. Loved the view from the spacious bedroom. Great hiking and local seafood.

Peaceful Lakeside Maine Retreat
The home was in a beautiful location and it was so peaceful to wake up and look out over the water. The beds were comfortable and there was lots of space for our group to hang out. The host was very accommodating and answered all our questions quickly. Highly recommend!

Covered Bridge Cottage - Maine woods and river
From arriving to the hospitality throughout the stay to check out everything was just amazing!! Hidden gem for sure! Very relaxing cottage with a beautiful view. Very cozy, felt right at home. I used to live in Maine so returning for NYE and my daughter’s birthday and experiencing this after the fast pace living in Miami was an amazing experience, just what I needed!

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.

Peaceful Cottage on Maine Flower Farm
Perfect fall cottage so close to Portland! The cottage is so peaceful and quiet. But so close to Portland but you wouldn’t even know it. The farm is lovely and we took a walk down to the river on the property, it was so peaceful and so much land! If you are looking for a get away from a city, but want to be able to explore Portland and Kennybunks, this was the perfect spot. I don’t know if I’ve slept that good all year. Would definitely come back again. And we love Trooper the dog!

Charming Cottage on pristine lake - Smoke Free
An absolutely wonderful cottage on a beautiful lake. West facing so lovely sunsets. The water is clear, clean and warm with a convenient pontoon to swim out to and back. The facilities were wonderful we used the kayaks and paddle boards. There is a well equipped games room (pool, table tennis and foosball). It’s perfect to keep kids entertained or just to relax. Also an outside pickle ball court. Dave and MB are very generous and welcoming hosts. One of the best accommodations we have ever stayed out. Highly recommend. Dave and Caroline
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!!

McKeen's Riverside Retreat
I would recommend this place to anyone looking for a comfortable place to stay. It was my son’s wedding and I loved being able to come back from the activities to rest and relax . It was very homey.

Merrymeeting Midcoast Cabin
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 :)

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!

Private cabin w hot tub,skiing,firepit & mountains
This is a beautiful home that is very well maintained and cared for. Alexa's cabin was a great place for 5 of us to gather, relax, and enjoy. Kitchen has everything you need, the hot tub is fantastic during a spring snowstorm, the beds were very comfortable, and it provided ample space for us.

Riverfront cabin between Portland & White Mtns.
As advertised, but perhaps a bit smaller than it appears. Great location, and the host was responsive.

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.
Quick stats about holiday rentals with a kayak in Portland
Total rentals
20 properties
Nightly prices starting at
£75 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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- Ogunquit Beach
- Wells Beach
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