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

Rising Tide Times - quintessential Maine cottage
We thoroughly enjoyed our peaceful and quiet time of rest at The Rising Tides. The setting is absolutely serene. It’s very secluded and quiet, the perfect place for a week of rest and relaxation. We went hiking on the Cliff Trail (15 minutes away and a very nice hiking trail), watched the sunrise at the Lands End store on Bailey island (15-20 minutes), and kayaked in the cove. The grill was very nice and we enjoyed cooking on it regularly. The place was very clean and ready on our arrival. The host communicated very clearly. You will need to follow her driving directions as they are very clear and helpful. In our four days there we only saw 1 neighbor - and that was as we were leaving on the weekend. There’s a grocery store only 15 minutes away and we were able to stock up on our way there. Really, this was one of our favorite places we’ve ever stayed. We really enjoyed having a few options of things to do while also being able to just do nothing on our vacation in a quiet place.

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

Family Escape w/ Kayaks, Fire Pit, & Water Access
What a whimsical town! In the middle of nowhere So peaceful Yet, Wallace's General Store, right up the road Maybe a mile Amazing food and Sandwiches and just about everything under sun to Need So, just down the road is this Amazing Place! Three Sisters Farm Heaven Awaits Must check out

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!

Lilypad on Damariscotta Lake by Rocky Coast Rental
The location of this property is unbeatable. Close enough to town, but lakeside down a quiet wooded road. Kids were thoroughly entertained with the outdoors, and my son caught his first fish off the dock to round out a memorable weekend.

Heavenly 4bd farmhouse in Maine.
It was a great stay! The place was so spacious and peaceful. Brad was quick to respond and really helpful. If I were to come back here, I’d definitely stay here again. A great experience 10/10 recommend!

Summer Camp, Refined: Stunning Lakefront Retreat
The location was perfect! The lake was so beautiful and we had so much fun using the kayak, canoe, and paddle boards. Everything was well provided for and any issues were resolved quickly. Sarah’s hospitality was amazing and it was such a memorable time for our big group :)

Brand new Scandinavian cottage: dock & kayaks!
This place has the best of what Maine offers. A ocean view with a pebbled beach on the front side with plenty of rocks and sea glass hunting and a quiet cove on the back that you can explore with the two supplied kayaks. The location is very inviting and the neighbors were friendly and gave us some great insight into the local area. There is plenty to do within an hour of the house from shopping, exploring other beaches or getting a taste of the local cuisine. If you like oysters we would recommend OystHERS in Bath. Our favorite beach was Popham where you can watch the harbor seals play at the mouth of the river. Overall this was a great family getaway and one that made lasting memories.
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!

Lakefront Home, Sandy Beach, Belgrade Lakes, Colby
Hillary's home was so cozy, beautiful, and just overall a wonderful place to visit. Beds super comfortable. Kitchen had everything you need and more. The view of the lake was so beautiful. I could go on and on.... Hillary is so easy to get along with. Answers all questions and gives great advice of the area and things to do and see. Overall Fantastic! Christ's local convience store has everything!! Our stay was terrific.

Your private waterfront B&B retreat in Maine...
I stayed at Liz and Alex’s stunning place at the beginning of September. This was either my 3rd or 4th time and I love being there. The quiet and the utter peacefulness of being literally on the banks of the estuarial river is amazing. Although I was only able to be there for 2 nights this time, I was recharged and ready to go back home when I left. On other visits I’ve taken advantage of being near the delightful town of Damariscotta, Pemaquid Point Lighthouse, Hidden Valley Nature Preserve, Muscongus Bay Lobster dock, the Audubon preserve in Bremen, and so many others. On this visit I stayed put, letting the inward and outward flow of the river soothe me while I read and wrote. On this visit I also had a nice long chat with Liz, a remarkably talented woman. See her book and ask about her films when you go.

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.

Driftwood Cottage | Lake Great Pond | Dog Friendly
Alana's home was more than we expected. The home was spotless and well equipped for our quick stay. She is very accommodating and responds to questions immediately. We would definitely stay again if we're in her area.

The Rocky Road Camp on East Pond
Two things stood out to us: Tim and Melissa were fantastic hosts. Responsive, flexible, and went out of their way to make us feel at home. If anything, they kind of undersell the lakeshore. Beautiful, peaceful, and a large area. We were here too early in the season to take full advantage, but this must be heaven in the summer. Hope to come back during kayaking season.

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

Cozy Lakefront Cabin * CampChamp
Loved this nature find...we swam, we canoed, we fired up the campfire with s'mores galore...with pristine views! All as described and great thoughtful touches in the cabin and yard. We had a nature oasis here that was hard to leave...but we also had some fun finds locally with dinner across the pond at the stunning Toddy Pond Farm! And we meandered over to The Lost Kitchen shop which is only 20 mins away.

Rustic Family Cabin on China Lake
We come every year. It’s a great quiet place.

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!

Off Grid Rustic Private Cabin
Masha's oasis cabin was just what we needed this weekend. It was so peaceful and private. No lights- just stars, no wifi- just connecting with each other. Masha was such a thoughtful host as well and made sure to check in with us to make sure we didn't need anything else. The cabin is also about an hour and a half from Acadia which makes for the perfect day trip!

Rustic Cabin on Beech Hill Pond near Acadia
My mother and I stayed here for a peaceful weekend and a nearby wedding. As lifelong Mainers, we were looking for a rustic camp on the water with a screened porch, and this place delivered. We spent our time reading, napping, walking, and even doing a little work (the internet was surprisingly fast). It was so nice that we could include our small dog with us as well. While the camp has a rustic charm, it’s thoughtfully outfitted with modern comforts: comfy beds, quality linens, a smart TV, reliable Wi-Fi, and a well-stocked kitchen. The hosts even provided extras most don’t—like paper goods, baggies, matches, and toiletries—and were nearby if anything was needed. They even included shower essentials if you happened to forget any. The sunrise was spectacular from the front porch. Loons swam by daily. Overall, we enjoyed our stay and wish we could have extended it---we would definitely book again! Thank you for being amazing hosts!

3 Evergreen
We had a wonderful stay! The location is perfect, the house was well stocked and we felt right at home. The dogs loved the dock on the lake. Listening to the loons on the porch while drinking our coffee was truly special. We would absolutely stay with Lauren and Warren again!

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!!
Quick stats about holiday rentals with a kayak in Waldoboro
Total rentals
20 properties
Nightly prices starting at
$116 SGD 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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- Popham Beach State Park
- Samoset Resort
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Pemaquid Point Lighthouse
- Wolfe's Neck Woods State Park
- Maine Maritime Museum
- Bradbury Mountain State Park
- Rockland Breakwater Light
- Hero Beach
- Sand Beach
- Three Island Beach
- Spragues Beach
- Pinnacle Park
- Eaton Mountain Ski Resort
- Head Beach
- Narrow Place Beach
- Pebbly Beach
- Lost Valley Ski Area
- The Camden Snow Bowl
- Lighthouse Beach