Holiday rentals with a kayak in Kennebunkport

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House rentals with a kayak

Superhost
Home in Shapleigh
5 out of 5 average rating, 3 reviews

Lakefront Home with Private Dock and Kayaks/SUPs

JoelRating, 5 stars1 week ago
Staying at Michael's lake house was the perfect retreat for our family. The first thing that stood out: The quiet. The house is on a cove just off the main lake, and it's so peaceful. We started our mornings with coffee on the screened in porch (yay no mosquitoes to worry about with kids!) and then spent the days kayaking, paddleboarding, and lying in the hammock. The lake itself is gorgeous and there's a sandbar that our girls loved! Meals were a breeze. The kitchen had everything we needed and was a lovely space to cook in (not to mention clean!). We grilled a couple of times too, which, for us, is a vacation must. It rained a little bit while we were there, but the house was well stocked with board games and honestly, everything was so beautifully decorated, it was just as relaxing indoors as outside. We'd totally come back here again. Thanks for a wonderful stay! Joel
Superhost
Home in Harpswell
4.9 out of 5 average rating, 115 reviews

Rising Tide Times - quintessential Maine cottage

AnthonyRating, 5 stars8 months ago
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.
Guest favourite
Home in Old Orchard Beach
4.96 out of 5 average rating, 147 reviews

Luxury 6 bedroom Beach House 50 ft from beach

JacobRating, 5 stars2 weeks ago
The house was beautiful and worked perfectly for our group! Check in was very easy, and the house was spotless when we arrived. My favorite part it was the yard - perfect for a big barbecue with a large group.
Guest favourite
Home in Kittery
4.94 out of 5 average rating, 140 reviews

Gorgeous Waterfront Home with Dock and Beach

KristiRating, 5 stars2 weeks ago
We spent the weekend here catching up with friends and couldn’t have asked for a better spot. The house was cozy and welcoming from the moment we arrived, with beautiful views all around. We’re so thankful we got to stay and make the most of it. There’s so much to do nearby, and it’s just a quick drive to Portsmouth, NH, which has so many great places to explore. Rachel also shared some fantastic recommendations that made our trip even better.
Guest favourite
Home in Middleton
4.94 out of 5 average rating, 171 reviews

Blue Breeze - Private lakefront w/ Hot Tub

LynnRating, 5 stars1 week ago
We would definitely go back for another stay. Carl is a wonderful host and was very responsive and helpful. The house is beautiful and is located in such a tranquil and scenic location. We are a family of 6 along with our black lab and everyone fit comfortably. I highly recommend this place for a family get away.
Guest favourite
Home in Phippsburg
4.97 out of 5 average rating, 88 reviews

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub

PeggyRating, 5 stars2 weeks ago
We loved staying at this cabin near Popham beach, the house was beautifully renovated. The renovation kept the cabin feel, yet at the same time felt updated and modern. I'd stay there again in a heartbeat.
Guest favourite
Home in North Berwick
4.88 out of 5 average rating, 64 reviews

The Lake House

KatieRating, 5 stars3 weeks ago
If you are looking for a quiet and relaxing stay surrounded by beautiful scenery, this is the place for you! The house itself is beautiful and set up well, with multiple common areas and private bedrooms. The host, Noah, was very responsive and helpful, and the check out instructions were simple and easy to follow. On my visit we had 3 couples in the house and had plenty of room. I highly recommend staying here!
Guest favourite
Home in Shapleigh
4.96 out of 5 average rating, 150 reviews

Secluded Lakehouse/2 private docks/Hottub/big yard

NancyRating, 5 stars1 week ago
We enjoyed our stay at this beautiful home. Lots of amenities and the hosts are very friendly and quick to respond to any questions. It was roomy for our family of 5 and the beds were really comfortable. I’d say it easily accommodates 6-7 people. If you are adventurous and don’t mind sleeping in a small loft or a basement setting you could fit 10-11.

Cottage rentals with a kayak

Superhost
Cottage in Conway
4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

TeraRating, 5 stars8 months ago
This place was really nice! Its on a beautiful lake with a lot to do! Jessica had plenty of kayaks, canoes, and life vests. The surrounding is beautiful and peaceful. The location is great with plenty of restaurants and shopping nearby. It's also very close to many great hiking areas Mt Washington.
Top guest favourite
Cottage in Middleton
4.99 out of 5 average rating, 103 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

StephenRating, 5 stars2 weeks ago
They were accommodating, flexible, and very gracious. They had an entire binder of information with details about where to find fans, towels, flashlights, how to work the shower, heat, grill, and about anything else you can think of. It also had emergency services, restaurants, places to have a good time, and good details about checkout expectations. Overall we were extremely happy with the property and our stay, and were honored by the personalization they did for us specifically as it was our Honeymoon and they wrote us a custom note by hand for when we arrived. Highly Recommended - Will Rent Again!
Guest favourite
Cottage in Windham
4.82 out of 5 average rating, 141 reviews

Cozy camp near highland lake

BenRating, 5 stars1 week ago
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.
Guest favourite
Cottage in Conway
4.94 out of 5 average rating, 345 reviews

20ft from the Water with Mountain View!

AlisonRating, 5 stars1 week ago
Loved our stay at this peaceful lake. The house is perfect- cozy and has everything you need. We loved paddleboarding and the access to cute downtown North Conway is ideal!
Guest favourite
Cottage in Topsham
4.93 out of 5 average rating, 253 reviews

Cozy waterfront home on Merrymeeting Bay.

EmilyRating, 5 stars1 week ago
Loved our time here! It’s about a 40 minute drive from Portland and then 5-10 from Brunswick. The neighborhood is quiet and perfect, exactly what we needed to relax! We loved coming back from Portland and grabbing dinner and gelato in Brunswick, such a nice way to unwind from a long day. Highly recommend and would love to stay here again :)
Guest favourite
Cottage in Standish
4.92 out of 5 average rating, 119 reviews

Peaceful Lakeside Maine Retreat

TeaganRating, 5 stars2 weeks ago
Janet’s place in Standish was great and we could not have asked for a better host. Apart from the home itself, Janet was very friendly and responsive. She even proactively offered early check in / late check out, extremely unexpected and appreciated! Would absolutely recommend this BNB 10 times out of 10.
Top guest favourite
Cottage in Middleton
4.97 out of 5 average rating, 152 reviews

Beautiful Lakeside Cottage

JonathanRating, 5 stars3 days ago
My wife and I wanted to have a lakeside getaway to kick off the summer! The weather was a bit colder than we had hoped, so we ended up enjoying the cottage to its fullest, which was a much needed and relaxing stay with everything we needed right there. It was very cozy and the lakeside view was wonderful, especially in the mornings. The owner was also very responsive to messages, making the experience seamless. We hope to visit again!
Superhost
Cottage in Freedom
4.79 out of 5 average rating, 483 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Leigh AnnRating, 5 stars3 weeks ago
Helen was actually wonderful. She returned calls and everything. It was a great place to stay beautiful and hope to stay there again someday.

Cabin rentals with a kayak

Top guest favourite
Cabin in Windham
4.92 out of 5 average rating, 205 reviews

Private Hilltop Cabin, Lakes and Trails Abound..

PeterRating, 5 stars8 months ago
We had the absolute best time at MJ’s place, highly recommend !! The house is spatious yet very cozy and quiet, with a nice back porch to sit and enjoy the surrounding woods! Home is also very close to town and to Poryland/coastline, and the cleanest lake to swim in that we’ve ever been to! MJ was very helpful and quick to respond. Stay here! We hope to return sometime soon!!
Superhost
Cabin in Raymond
4.93 out of 5 average rating, 154 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

WaltRating, 5 stars8 months ago
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!
Guest favourite
Cabin in Bridgton
4.92 out of 5 average rating, 128 reviews

Private cabin w hot tub,skiing,firepit & mountains

ChloeRating, 5 stars2 weeks ago
We absolutely loved our stay at Alexa’s cabin. We enjoyed the hot tub, fully stocked kitchen, and truly felt like we could disconnect from the world to connect with those around us. Alexa was a great communicator, provided detailed instructions and local recommendations that were spot on. Don’t hesitate to book this Bridgton escape!
Top guest favourite
Cabin in Limerick
5 out of 5 average rating, 62 reviews

Peaceful and Rustic Lakeside Cabin

ShelbRating, 5 stars2 weeks ago
This spot was AMAZING, and Eva was such an incredible host. For a large party like mine, all of us felt comfortable, and there was more than enough space where we were not cramped in. The recommendations that Eva provided were accurate and very resourceful. I have reached out to her a few times to ask questions and extend my gratitude for being such an amazing host, and she was by far one of the friendliest hosts I have ever encountered. My family and I were disappointed that we needed to leave, but we will most definitely be coming back again next year!
Guest favourite
Cabin in Denmark
4.95 out of 5 average rating, 188 reviews

Maine Lakes-Pleasant Mt-Private Trails

BillRating, 5 starstoday
Third visit in three years for a weekend fishing getaway. Great location, beautiful property. Excellent hosts. Looking forward to a return visit.
Guest favourite
Cabin in Wakefield
4.97 out of 5 average rating, 253 reviews

Beautiful Log Cabin on Belleau Lake -2900 sqft!

AlyssaRating, 5 stars1 day ago
We had a great time at this location. The kayaks were great and the location was perfect. We had everything we needed for a fun getaway.
Guest favourite
Cabin in Denmark
4.97 out of 5 average rating, 104 reviews

Lake Front with Private Dock - BRAND NEW Furniture

AaronRating, 5 stars2 months ago
This is an absolute beautiful place to stay. There is no question, I would 100% stay here again. My family had an amazing time here. Darryl was very easy to communicate with and made the stay very easy. If you’re looking for a clean and quiet place to stay, look no further.
Top guest favourite
Cabin in Brownfield
4.97 out of 5 average rating, 66 reviews

Dog Friendly Waterfront Cabin near White Mountains

CarrieRating, 5 stars2 months ago
We had a great week in the woods at the Riverbend Cabin. We happened to be there right at the start of a spring thaw and the river and yard went from snow-covered to completely unfrozen in two days, so we got to see it change dramatically. Our dogs absolutely loved running around the property and going in the water. The bedrooms were cozy for myself and my teens. We had everything we needed to cook, watch movies, play games and relax on our spring break. Although there wasn't very much to do in town itself, we were happy to wander a few days. We found an Escape Room in South Portland, had a great dinner and went to a show in Portland one night, and highly recommend Hiking with Goats in Gray, ME. Overall, it was just what we needed for an escape from work and school for the week. We would definitely stay again!

Quick stats about holiday rentals with a kayak in Kennebunkport

  • Total rentals

    20 properties

  • Nightly prices starting at

    $282 SGD before taxes and fees

  • Total number of reviews

    740 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore