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

Sugarmaple Lakehouse - Sebasticook Lake Newport ME
Great location. Woke up to the sounds of birds. very responsive. I would have given it a 5 star all the way, David was amazing and responded in a very timely manner. But, the turn over service could have been much better. The previous guest left a wine bottle in the automatic fridge ice dispenser and it was unfounded until my family found a large peice of glass in their drink, serious hazard to drink glass. Should have been spotted by the turn over service but, who would check the ice maker for a bottle a wine? I understand that. Very uncommon and unfortunate for us. David responded in a very fast manner and gave us options to accommodate the situation. I would have left a 5 star if this was the only thing but everything was so unorganized in the kitchen, they had everything but nothing made sense to why it was there. Sink didn't drain. There were also stains on the sheets and a pizza box left by the fridge that wasn't ours. Little things but the turn over service was a let down.

Waterfront Gem walkable to Restaurants!
a wonderful place to stay.

LUX Designer Private Waterfront
We came here for a private getaway on our honeymoon and it did not disappoint. The price was a bit much, but for such a special time I felt it was worth it at the time I booked, and worth it it certainly was. beautiful, quiet, serene, it was perfect for a getaway. I would absolutely recommend, and I already have, this stay. 10/10

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Great rental property in a great place.

Cozy Waterfront Home With Breathtaking Views!!!
We had an amazing time. TJ was very responsive and gave his secrets for fishing! He also accommodated a request that was an overlook on my part. I can’t say enough good things about the place itself or how nice TJ was. It was a phenomenal experience all around!

Riverside
This was my 5th time going there and I love it! The house is so cozy & very clean. The property is large and the view is breathtaking over looking the river. They are also pet friendly so we were able to take our Lhasa Apso Revy on vacation with us. Besides how great this Air BnB is, my favorite is the hosts Kent & Tish! They are wonderful people. They are kind & friendly, & have such beautiful souls. They have become family to me! I highly recommend getting this air bnb!! Thank you again Tish & Kent! Ian, Revy, & I are always happy to see you!!

Waterfront Farmhouse with Modern Flair!
We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba
My wife and I completely enjoyed our stay at Ani’s place. She literally thought of everything any guest could ever want. Beautiful surroundings…walking distance to the Fish Ladder….a couple of miles to all the restaurants downtown. And the place itself is immaculate. The kitchen was perfect for eating in every night. This place is an absolute no-brainer to rent and we can’t wait to return!!!
Cottages with a kayak

Privacy with spectacular waterfront, Lilla Stuga.
My family and I had the pleasure of staying here while celebrating our daughter’s graduation from Colby College, and we couldn’t have asked for a better experience. This was such a meaningful milestone in our lives, and the accommodations provided the perfect home base for our celebration. From the moment we arrived, we felt welcomed and well cared for. Despite the cold Maine weather, the warmth of the space and the thoughtful touches throughout our stay made us feel comfortable and at ease. We truly appreciated having a cozy and convenient place to return to after the graduation festivities. Thank you for playing a part in such a special and unforgettable weekend for our family.

Lake House on Three Mile Pond with Amazing views
Mark was awesome. The place was just what I needed to get away from the grind of life. I recommend him to any and everyone.

Gorgeous lakefront, sunsets, kayaks, fire pit
Leslie was very responsive and helpful before the trip. The place was even more beautiful than expected. The Google address leads to a few houses before, but the description of the driveway helped us find the right location. It was the perfect location to relax for the weekend.

Hidden Haven A Rustic Retreat In St. George, Maine
Mischele really thinks of a traveler when she sets up her place! The extra touch of orange juice, creamer, coffee, freshly baked breakfast is great! Everything is there. Convenient to many great restaurants.

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 :)

Classic Lakefront Maine Cabin
What a beautiful location! David is a great host. He made sure we had good directions, tips for the area, and was quick to answer any questions. The lakeside cabin has absolutely everything you need to have a peaceful, relaxing vacation. The view of the lake is spectacular. The cabin is very clean, has a well stocked kitchen, comfortable beds and Echo lake is a gorgeous pristine lake. Every morning, we enjoyed our coffee on the dock. We swam, kayaked, canoed and even tried out the paddle boards that came with the house. We would love to come back! Thanks!

Bass Point Lakeside Cottage: Livermore, Maine
I had a wonderful 4 night stay at the lake house and couldn't have asked for a better place to spend the little getaway. It is beautifully located on the lake and has this huge window in the living room from which you have an amazing view. The house has everything you need, even washing machine and dryer in the basement. I would 100% recommend this unique place! Christine has been super helpful throughout my stay.

Cottage on Long Pond in Belgrade Lakes, Maine.
Our second time staying. Beautiful location, close access to the water. Thoughtful features inside. For wintertime stay the driveway was clear and we were able to keep very warm in the cabin, even on the coldest of days!! Tara is a responsive, kind and helpful host. Would definitely visit again!
Cabin rentals with a kayak

Lakefront Stunning Home, just 35 min to Sugarloaf!
Absolutely beautiful views. Peaceful location. House is very well equipped with board games and basic amenities!

Loon Lodge Canaan,ME
We did not take much advantage of all the cabin had to offer; we were in the area for other reasons, and mostly using this as a place to sleep. That was kind of a shame; I hope we can get back there sometime to enjoy the lake and the games and the firepit and the kayaks and the cabin itself. I saw a review saying the beds were a little too hard? I disagree, I thought they were extremely comfortable. The only info I can think of that I didn't see in other reviews: we showed up very late at night, and it was hard to find in the dark (it's very obvious in daylight). It is at an intersection, but GPS sent us slightly past the intersection; it's actually on your left just before you get to the last intersection. Other than that, I agree with all the other positive reviews. Lovely place.

Hobb’s House - Year Round Log Cabin on the Water
This was our second time staying here. We love the beautiful and peaceful setting. Lots to do in the surrounding areas but also we love relaxing at the house by just sitting on the dock with a good book or kayaking/fishing in Hobbs Pond.

Charming cottage at the Lake!
Charming little cottage on the lake! Had a lot of fun, easy to get to town and the lake was serene and peaceful. Great place to stay!

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!

Thompson Lake, No Cleaning Fee Pine Point Cottage,
What an amazing hosts! When i check in they both came and visited and gave me a grand tour of things of the place. Showed where the lake was to kayak, recommended places to eat, and visited. Michael was quick to respond making sure i was doing great. I would totally go back and rent their place again! Thank you so much!

Mill Pond Waterfront Cabin On The Way To Sugarloaf
We had the most wonderful stay! We spent a week, celebrating our 15th anniversary, soaking in the views, enjoying the wild life and cozying up at the camp fire, enjoying one another’s company. The cabin was clean, stocked with necessities and perfectly decorated. The bed was comfortable and all the linens were clean, with very comfy pillows too! Lots of games were provided, and the view from the living room is stunning. You look right out onto the pond. We had some wildlife visit us, and a chipmunk we made friends with. Look for his little house entrance by the fire pit! He also loved perching on the cairns to watch us Explore the property and find some little hidden gems of beauty The locals were super friendly, Jon was very accommodating and responsive. We couldn’t have asked for a more perfect experience Thank you so much. We are looking forward to visiting again!!

Lakefront Cabin- Belgrade Lakes
We felt very at home. The place is even better than the pictures. Nice walking trails near house. The walk to the dock is a little steep, so walk carefully, especially at night. We are already looking forward to staying with Christopher next year!
Quick stats about holiday rentals with a kayak in Oakland
Total rentals
30 properties
Nightly prices starting at
$166 NZD before taxes and fees
Total number of reviews
960 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Samoset Resort
- Pemaquid Beach
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