
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

2 Acre Waterfront w/Canoes & Kayaks, Game Room
If you want a private, well furnished home in the woods with fishing access on the stream and 2 fire pits this is your place!! Staying at this house made a work trip for my crew and I, feel like we were on vacation for 2 nights while staying there. Worth the money and great hosts!

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!

House on Lake St. George
Corie was so responsive with answers to questions about wifi and check-in to fun day trips we should try while we are there. The view of the lake is the best and the swimming was wonderful. Plus loved the paddle boat. Very relaxing!!

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!

Modern Lake Front Home with Hot Tub
Enjoyed our stay. The screened in porch was our saving grace due to rainy weather. Very relaxing trip!

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
It was truly a beautiful family trip! The house was beautiful and the lake views were 👌🏻 we spend most evenings by the lake around the fire pit and created so many memories. Great restaurants in Camden and surrounding areas. We would definitely go back!
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.

Coastal Waterfront Tiny home in West Bath
What an awesome airbnb! The views are stunning and surroundings couldn’t have been more peaceful. The cottage itself was exceptional and had everything I needed and more. Wish I could've stayed there longer! 10/10 would recommend this place to anyone!

Driftwood Cottage | Lake Great Pond | Dog Friendly
This cabin was very comfortable with great amenities (cooking ware, laundry). The beds and linens were very clean and quite comfortable. We were each given two fresh white towels. The cabin is on a dead end street surrounded by A-frames and little cabins, pretty close together, but no so much thst it felt crowded. Its licated across the street from a lake. There is lake access about 5 houses down - a few minutes walk - down the road. We stayed in May and it was very quiet at night. Mostly, we saw no one, (being somewhat pre-season). But we met one neighbor on a walk who was very friendly and took a moment to say hello and pet put dogs. The local grounds were clean.

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 St. George Retreat
Amenities were perfect for what we needed, some peaceful R+R. The space was clean and inviting. Fishing off the dock was amazing.

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

Lakefront cottage
This lake house is wonderful for beautiful views of the lake in a comfy, cozy environment. The house is well stocked with anything you need and Bonnie is very responsive to any questions. We loved being able to go kayaking in the morning with an easy launch site right next to the house. Listening to the loons at night was so peaceful as well. We would highly recommend this house for anyone looking for a Maine vacation!

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
Our stay at Dave's lakefront cabin was exactly what we'd hoped for, and then some. This isn't just a rental; it feels like a genuinely preserved piece of Maine – authentic and full of character. Being right on the lake was the absolute highlight. The views are truly epic, offering stunning sunrises and peaceful evenings that we savored from the deck and the dock. It was the perfect backdrop for morning coffee and winding down after exploring. Dave is an exceptional host. He was incredibly welcoming and thoughtful, making sure we had everything we needed without ever being intrusive. You can tell he cares deeply about this place and his guests. The cabin is filled with thoughtful touches that are one-of-a-kind, from the cozy throws to the unique decor that tells a story, making it feel less like a temporary stay and more like a cherished home.

Magical Lakefront Cabin on 5 Acres-25 Mi to Acadia
Mandi and Michael’s place was a dream come true! Our jaws dropped the moment we stepped foot out of the car and walked the path to the cabin. As hosts, they thought of everything we could need and more. Our stay at the Happy Loon was better than we could’ve imagined. Thank you both for making our trip so magical. We appreciate your hospitality and for sharing your beautiful property with us.

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
We had a wonderful stay at Claire’s tideside. The scenery at her property is stunning. We had an awesome lobster boil with the fresh lobsters Claire dropped off. She was so friendly and we enjoyed talking with her. She is quite informative of the whole area.
Quick stats about holiday rentals with a kayak in Waldoboro
Total rentals
20 properties
Nightly prices starting at
₹7,747 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
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Samoset Resort
- Belgrade Lakes Golf Club
- Pemaquid Point Lighthouse
- Maine Maritime Museum
- Bradbury Mountain State Park
- Rockland Breakwater Light
- Wolfe's Neck Woods State Park
- Eaton Mountain Ski Resort
- Pinnacle Park
- Spragues Beach
- Sand Beach
- Hero Beach
- Lost Valley Ski Area
- Head Beach
- Pebbly Beach
- Pebble Beach
- Narrow Place Beach
- Bear Island Beach
- Three Island Beach