
Vacation rentals with a kayak in Waldoboro
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Top-rated kayak rentals in Waldoboro
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House rentals with a kayak

Rising Tide Times - quintessential Maine cottage
Stayed at Bethany's place for a long weekend at the end of the season. The location is unbeatable, the house is situated on its own little peninsula in a stunning cove; it feels very private and has amazing views of the water. There's tons of outdoor space and seating, along with several kayaks. The house itself is clean, quiet, and peaceful, although it's definitely small--probably best for one or two people, or a couple with a small child. Access is down an unpaved road but Bethany's very clear instructions made it easy to find, and she was responsive to any questions we had. Harpswell abounds with areas to hike and explore, lots of good places to eat (though you will definitely need a car) and is less than an hour from Portland and only half an hour from Freeport.

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!

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!

Walk Anywhere, Immaculate , Fishing, Pet Friendly
5 stars! Clean and quiet, great location sandwiched between Rockland and Camden. Very fortunate we could bring our pup with us for the weekend.

Riverside
We had an amazing time over valentines day weekend. There was a snow storm and Kent snow blowed around our vehicle to make sure we could get out. The house is very comfortable and peaceful, amazing view of the river and just off the road enough to not be bothered by passing traffic. Definitely recommend!!!!

Serenity on Sheepscot Lake
Our group of friends and family really enjoyed staying at this peaceful winter getaway house! We are already talking about coming back up in the summertime. The toys and games made my kids so happy and kept them well-entertained. Perfect amount of space for our big group! Lori was flexible and responsive, a wonderful host! Thank you again 🛷

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 Home fully equipped
Leslie’s home is exactly that, cozy, spacious, beautiful, peaceful, but above all it feels like a real home. Leslie was welcoming and gracious, she went above and beyond, I would certainly consider her a friend after staying there. I highly recommend this spot!
Cottage rentals with a kayak

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!!

Hidden Haven A Rustic Retreat In St. George, Maine
Beautiful cabin in quiet and peaceful surroundings. Closes to attractions and multiple small towns with things to see and discover. Michelle and Dan were great hosts, everything we needed was in the cabin! They had a book of area things to do. They answered right away when we texted. I would definitely recommend their place!

Near Waterville | Lake Great Pond | Dog Friendly
We had a wonderful stay with our family and we were happy our dogs were welcome to come with us.

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

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.

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

Quiet Lake Front Cabin
Nice place and location. Have all you need.

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

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 :)

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!

Smitten - you will be - Hear Silence.
The location is magical . Loved waking up and seeing the scenery. The trail was really well maintained given all the snow. We've had a wonderful hike to the pond seeing only nature, not one person on the trail. It was fun stopping and trying to identify all kinds of animal tracks along the path. We are thinking of coming back in the spring or summer. Thank you for muffins Toby and Peter!!!

Cozy log cabin on private pond, near Reid St Park!
Enjoyed a long weekend here with my wife. Nice cabin, very cozy and nostalgic. Loved the getaway and your space was perfect for that.

Roxie the Tiny Cabin on 100 acres
Lovely location, and cozy little cabin, close to Damariscotta. My boyfriend and I took a weekend away and I told him I just wanted to be in the middle of the woods for a night. Enjoyed the hammock chairs and home cooked breakfast on the porch, despite the rain. Only regret was not meeting Sherri and/or Joel since I opted for self-check-in. Hope to return!
Quick stats about vacation rentals with a kayak in Waldoboro
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ331 before taxes and fees
Total number of reviews
490 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Wifi availability
10 properties include access to wifi
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- Fox Ridge Golf Club
- Brunswick Golf Club
- Popham Beach State Park
- Belgrade Lakes Golf Club
- Samoset Resort
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Sand Beach
- Narrow Place Beach
- Pemaquid Point Lighthouse
- Spragues Beach
- Pinnacle Park
- Bradbury Mountain State Park
- Falmouth Country Club
- Andrews Beach
- East End Beach
- Lost Valley Ski Area
- Martindale Country Club
- Farnsworth Art Museum
- Bear Island Beach
- Hero Beach
- Hunnewell Beach
- Indian Camp Beach