
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

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.

Lakehouse with 100ft of private waterfront
My wife and I spent our first year anniversary in this wonderful home. We had a great time enjoying the fall colors and over looking the beautiful pond, especially in the morning as the fog broke. Within 15 minutes there were several grocery shopping options, restaurants, and breweries. Perfect balance of being in a quiet setting but having amenities nearby. Would recommend and hope to go back next autumn!

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!

Beautiful home on Wyman Lake
Beautiful home right in wyman lake. Nice place is a really nice area. Check in was super easy and Amber was excellent. We thoroughly enjoyed our stay, thank you amber!

Cozy Waterfront Home With Breathtaking Views!!!
LOVED Tj's place! Wish I were staying there for vacation purposes, instead it was just while I was moving and movers had already taken all my furniture. But, right when you walk in, there's the water... The interior felt like home. Was able to walk down to a restaurant and there's a park across the street and a smaller one right next to the house. Didn't get to use the kayak since it was snowing... :-) Highly recommend Tj's home for whatever purpose. I will definitely try to get this home when I make it back up there!

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.

Lakefront Log Cabin on Pleasant Lake
This was our second stay with Devon and as usual it did not disappoint! It is exactly what we needed for a quiet getaway. It is very serene with sounds of the Loons echoing across the lake. Did not see a car or person in 4 days which was great. Devon was always in touch if needed and accommodating. Great kitchen with everything needed for a snack or a full meal. A very relaxing stay!
Cottage rentals with a kayak

Gorgeous lakefront, sunsets, kayaks, fire pit
This place was quiet and close to the lake exactly what our group need for our yearly ice fishing trip Leslie was very responsive and easy to talk to would definitely recommend and make a return trip

Quiet Lakeside Cottage
Our family had a lovely stay at the Lupine Cottage. Such a peaceful spot. We enjoyed getting out on the water in the kayaks and sitting out in the Adirondack chairs listening to the loons and barred owls call. Nice central location for exploring Acadia and the mid coast. Thanks Kim & Stacy for the precious memories!

Lakefront cozy cottages w/ dock, canoe & fire-pit!
We absolutely love staying here! We come back year after year and love the cozy Maine cottage feel to this place. The perfect relaxing vacation and will definitely return for more!!

Near Waterville | Lake Great Pond | Dog Friendly
The place was beautiful and exactly what we needed! I would definitely recommend staying here.

Waterfront Cottage
Amazing place, it was exactly what we needed.

Cozy waterfront home on Merrymeeting Bay.
This is our second stay here and we just love the location. looking out over the river is so relaxing.

Loons Rest- Maine Quintessential Cottage
Loons Rest was the perfect get away spot for our 40th anniversary. We were lucky to enjoy the swimming dock in mid September as the daytime temperatures were in the upper 70's to low 80's. The lake was pristine and was warm enough for swimming still. We enjoyed watching and hearing the loons as well as the eagles and kingfishers. We loved the outdoor fire pit when the evenings turned cool as well as the indoor fireplace which is a work of art! Also the was plenty of well seasoned firewood. Everything about this place is very well thought out. If they don't have it you don't need it! The kitchen was well equipped and we were happy to find that there was everything we needed to prepare pizzas to cook on our solo stove pizza oven that we had brought along! John is a great host and responded quickly to any questions we had. Would highly recommend Loons Rest to anyone who is looking for a peaceful and relaxing spot to vacation.

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

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub
My friends and I had a great time relaxing at this beautiful place. Aqeel and Michelle were extremely responsive and helpful when necessary. We would stay again!

Charming Lakefront Cabin
This location was absolutely stunning! Brad was incredibly accommodating and even ran over with a high chair after our check out because we had two families with young children. The yard was cute and we loved playing outdoor games in the communal grass area right by the house. The house was very cozy and the perfect space for our families. I wish we stayed longer!

McKeen's Riverside Retreat
The cabin was just as advertised. A quiet clean space!!

A Serene A-Frame Cabin with Hot Tub
We had a great late October stay for our honeymoon. The cabin was definitely warm enough for the 30 degree temperatures. Hot tub was amazing, that was clean as well. The outdoor kitchen was very convenient, even when it rains the kitchen is still covered. We had an amazing stay, will be visiting again!

Rustic Family Cabin on China Lake
I loved this place! Enjoying coffee and meals outside on the deck overlooking the lake and beautiful surroundings of nature. I felt safe there and was a charming neighborhood. I loved that there were boats to use and a dock to watch sunset an autumn harvest moon over lake! Jess was the perfect host and made sure everything was great when I arrived. She was very helpful when I had any questions and I am looking so forward to going back there again! Thank you Jess for sharing this wonderful place!!!

Hobb’s House - Year Round Log Cabin on the Water
Connor was an AMAZING host! From the very beginning, he was always very responsive, and was consistently available to answer my questions promptly. His cabin on the lake was so cozy, it truly felt like our home away from home. It was beautifully decorated, peaceful, serene, well-stocked with anything that one could need. His recommendations were extensive and were very much appreciated. We were celebrating our 30th wedding anniversary and really loved being able to stay there with friends for a few days before departing for another excursion. It gave us time to celebrate and make some great memories with them - something that we will always treasure! The worst thing about this cabin? - Having to leave it in the rearview mirror! Connor, thanks so much for sharing your beautiful cabin with us. You can count on us to be back in the future! Thank you!

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!

Get away at Crystal Lake
Great cabin, location, and hosts. Our group had a great time coming back for our second trip here and would highly recommend. 5 stars all around.
Quick stats about vacation rentals with a kayak in Oakland
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ367 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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- Saddleback Ski Mountain Maine
- Fox Ridge Golf Club
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Samoset Resort
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Sugarloaf Golf Club
- Narrow Place Beach
- Spragues Beach
- Hermon Mountain Ski Area
- Pinnacle Park
- Dragonfly Farm & Winery
- Lost Valley Ski Area
- Martindale Country Club
- Black Mountain of Maine
- Titcomb Mountain
- Farnsworth Art Museum
- Bear Island Beach
- The Camden Snow Bowl
- Rockland Breakwater Light
- Islesboro Town Beach
- Maine Maritime Museum
- Three Island Beach