
Vacation rentals with a kayak in Oakland
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Top-rated kayak rentals in Oakland
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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.

Lakefront summer getaway cabin for 6
We had a great week at the cabin! The view is amazing and it was so relaxing. Courtney was very responsive and attentive. Highly recommend for a cozy getaway in a beautiful setting.

Great Pond Lake House With Western Views
Donna's lake home is a beautiful getaway spot in Maine. The house was immaculate upon arrival and our party couldn't have asked for a more enjoyable stay. Thank you again!

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

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!

Waterside Getaway
Sarah went above and beyond for my fiancé and I. We stayed in her cabin for our anniversary and we were greeted by a lovely vase of flowers, s’mores fixings, and a beautiful card. Though we checked out June 2nd she made sure we had kayaks for our entire visit (only available starting June) and dry firewood! She was extremely kind and responsive. The property was stunning and matched the photos. We felt very much at home and will be staying again in the future! Thank you Sarah for letting us stay at your family camp!
Cottage rentals with a kayak

Lakefront Cottage on Tracy Pond, New Hampshire
Anna was incredibly communicative and her place was clean, quiet, and exactly what we were looking for. We especially loved her two little greeter cats!

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.

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.

Your own private getaway on Pushaw Lake!
Robert was an incredibly responsive, kind and proactive host. The space is exactly as described, comfortable and Robert has thought of everything. The surroundings are amazing, we loved listening to the loons, watching the chipmunks & even got a glimpse of a beaver one morning. Kayaking was great, with the equipment and dock easy to access and use. We visited Acadia and loved having such a quiet respite after long days exploring the beautiful area. Highly recommend staying here, already thinking about our next trip back!

Hidden Haven A Rustic Retreat In St. George, Maine
Really enjoyed our stay at the cottage. Everything was clean and cozy. Great time going through the DVDs, board games, and close access to Rockland town. This was an amazing stay and one for the scrap books!

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.
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!

McKeen's Riverside Retreat
We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..

Merrymeeting Midcoast Cabin
This was my second time staying at Terrill’s place and it was just as lovely as I remembered! It’s such a peaceful place, surrounded by natural beauty, to relax and unwind. I’ll definitely be back again!

Waterfront| Fire pit| Deck|Kayaks
This place was exactly what I wanted it to be. A great place for me and my family to relax and enjoy the outdoors. We would definitely recommend it!

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!

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!
Quick stats about vacation rentals with a kayak in Oakland
Total rentals
30 properties
Nightly prices starting at
G$20,914 GYD 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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- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Samoset Resort
- Saddleback Ski Mountain Maine
- Belgrade Lakes Golf Club
- Sugarloaf Golf Club
- Maine Maritime Museum
- Dragonfly Farm & Winery
- Hermon Mountain Ski Area
- Rockland Breakwater Light
- Eaton Mountain Ski Resort
- Pinnacle Park
- Spragues Beach
- Lost Valley Ski Area
- Pebble Beach
- Narrow Place Beach
- Bear Island Beach
- Three Island Beach
- Black Mountain of Maine
- Farnsworth Art Museum
- The Camden Snow Bowl
- Martindale Country Club