
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.

Gran Den Lakefront Home Near Acadia
Great stay for our family of 5 adults and 3 toddlers! Lots to do and great proximity to Acadia/Bar Harbor. House was well supplied with clear instructions. Brady also connected with us before the stay and kept in touch for anything that came up as a concern. Thank you!

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

Most Sought After Property on Lake Damariscotta!
The house was great and matched what the description was. Very spacious and everything needed. Matthew was also very responsive when I had questions. Would stay there again for sure!

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 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.

Cozy camp near highland lake
Lori was a wonderful host for our trip up to Maine. My girlfriend and I enjoyed doing yoga in the entrance room when it rained and a nice sunrise kayak trip out on the lake across the street. My in-laws stayed with us too and we all had great laughs together and enjoyed good food all weekend long.

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.

Super cute waterfront cottage
10/10 would recommend for a gorgeous, peaceful retreat in Maine. Calvin and Christine were excellent hosts - great recommendations and very very responsive. The home offers beautiful natural light, good amenities and isn’t too far from the main town. The view of the water is absolutely incredible especially when you go down to the dock. We ended up enjoying most of our meals at the house and the kitchen was well-equipped for easy meal prep. If we’re ever in the area again would definitely rebook!
Cabin rentals with a kayak

Lake Cabin in the Trees
We stayed here to be near Bates college for graduation weekend. We felt right at home! The cabin was warm and inviting... cozy, clean and safe! It was so secluded, with a gorgeous view over the water. We would love to return when we can simply stay in the cabin and enjoy the peace and quiet.

Cozy Camp Round Pond - Kayak, Swim, Bonfire, Games
We had a great stay at Leah's cabin. The place was warm and cozy, and we enjoyed the lookout onto the beautiful frozen lake. Leah was very proactive and responsive. A great stay!

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.

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!

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!

Cozy log cabin on private pond, near Reid St Park!
When you are out exploring a new area, the perfect way to end each day is in a cozy, relaxing secluded cabin in the woods, and this is just what Destie and George provide at The Little River Retreat. Their cabin, with its wide, inviting front porch with a sunrise view of mist over the pond, is just the place for morning coffee. They have thought of everything in terms of stocking the cabin, including rainy day and evening entertainment for all ages. I definitely overpacked as so much was provided by them! It is so nice to go to a place where you can take a step back from daily life and it's stresses, and just relax. Thank you for 6 wonderful days.

Tideside Maine
This is our second time staying at Tideside. We just love it here. The area is beautiful, location right on the water is amazing, and there are many little special touches around the property that just make it such a special place. Claire is fantastic to communicate with and very accommodating. We can’t wait to come back!
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