
Vacation rentals with a kayak in Portland
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House rentals with a kayak

The Cliff House
Extremely peaceful and relaxing! The rental is more like a home than a cottage/camp with its recent tasteful, pleasing, and very functional renovations (the flooring was well done and looked great; the mini-split system made it very comfortable even when it was in the 90’s; and, the new furnishings were attractive and comfortable). We thoroughly enjoyed ourselves!

Sebago Lake, ME *Lakeside*Hot Tub* just renovated
We thoroughly enjoyed our stay at Sebago Lake. The area is stunning, with nice access to the water, making it a perfect spot for exploring the surroundings. Colleen and Leo were incredibly responsive and welcoming, ensuring we felt right at home. We would absolutely choose to stay here again!

2 Acre Waterfront w/Canoes & Kayaks, Game Room
I love coming to Maine, and this was my first time staying at Rob's place—it was beautiful! Rob was more than accommodating and incredibly hospitable. The home is gorgeous, super clean, cozy, and very private. The game room was such a fun bonus! It was the perfect little getaway. Thank you so much, Rob, for everything! I will definitely be keeping this place in mind for future visits!

Waterfront Gem walkable to Restaurants!
Beautiful house on the pond! Perfect for our family of 4. It was comfortable and relaxing. Amy is a wonderful host! She checked in and made sure we had everything we needed. We really enjoyed our stay! Hoping to stay again sometime.

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!

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
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,
The cabin was very quaint and cozy for a snowy day. A quick walk to the lake and not too far from some cute shops and restaurants in Norway. Very responsive and friendly hosts. Incredibly clean and well maintained. Would stay again!

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.
What a beautiful thoughtful place! There were games to enjoy, a kayak, a wood stove inside, and fire pit outside. This place was such a beautiful gem!

Maine Lakes-Pleasant Mt-Private Trails
We had a great time here! The cabin was incredibly comfortable and cozy. We especially enjoyed the hiking trails out back!
Quick stats about vacation rentals with a kayak in Portland
Total rentals
20 properties
Nightly prices starting at
$100 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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- Wells Beach
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