
Vacation rentals with a kayak in Milton
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House rentals with a kayak

Private oasis on Lake Mousam all season activities
Every year we pick a place on the lake between Mother's and Father's day to celebrate over a weekend. We love to kayak and visit the local eateries while relaxing in nature. This year we were fortunate enough to find Katherine's home in Acton, ME for Memorial Day weekend. The house was spacious, comfortable, clean, and homey (and right on the lake)! Katherine and Nick were both very responsive and friendly with check-in check-out and we loved the places listed on their travel guide. The house is a short hour drive from Kennebunkport and Portland so we took some day trips during the rainy days and floated around the peaceful inlet of Mousam Lake when sunny. Leaving the inlet takes you to the rest of Mousam Lake where we saw motor boats, jet skis and one person wake boarding! Our old dog, Shaggy, had a blast and the long road leading to the property gave him the ability to run around without bothering any neighbors, who were all very friendly! Definitely worth a return visit!

Cozy Lakefront Cottage on Little Sebago
My family really enjoyed our stay at Justin's Cozy Lakefront Cottage on Little Sebago. It was exactly as advertised - a cozy lakefront cottage. We especially enjoyed the paddle boards, kayaks and a canoe (and plenty of life jackets) , as well as the dock and floating pier. This access made it easy to enjoy the lake all day. And the view of the stars from the dock at night was incredible. We enjoyed listening to the loons at night, and had many fabulous meals on the screened in porch. The inside of the cabin is very cozy and there are games to play and books to read. Justin gave us many great recommendations for places to enjoy in the area. In particular, we liked the lobster rolls at Fishermen's Catch and everything from The Good Life. It was easy to make day trips to Portland and Freeport. Overall, this was a very relaxing trip and everyone from age 12 to 60 thoroughly enjoyed themselves. Justin has thought of everything for you to have a wonderful vacation.

Lakefront -Kayaks,Ski Pats Peak,Fish,Dock
We had a wonderful (restful!) stay in Weare. Highly recommend this peaceful property right on the lake.

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim
We had a wonderful time. The house was perfect. It was a short walk to the lake. Very peaceful and quiet. Loved having 3 full bathrooms. It was a short drive to Conway for shopping and restaurants.

Riverfront! Close to Dock Square & Beach! KBK/KPT
My husband and I loved staying here for our honeymoon! This loft provided the perfect mix of relaxation and plenty of things to do being so close to Kennebunkport, downtown Kennebunk and Gooch's Beach. We loved sitting out on the porch every morning and exploring in the afternoon/evening. This Airbnb was super cozy and provided everything we needed for our vacation. We also loved meeting their dog, Dewey!

Gorgeous Waterfront Home with Dock and Beach
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.

Private Waterfront home
The home was exactly as described. There were plenty of towels, linen and beds for a group of 10. The home was spotless and was very comfortable. Anna-Lisa was an amazing host. She provided clear instructions for entry into the home, offered lots of recommendations and was very quick to respond to all inquiries. The she shed was a bonus for any mom needing a few moments away.

Waterfront w Kayaks, Pool table, Pergola, Firepit
Lovely place to stay. Right on the water. Comfy beds. Easy check in. Close to restaurants.
Cottage rentals with a kayak

Cozy Pondside Retreat with direct water access!
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.

Cozy camp near highland lake
Super cute little camp house good for a nice quiet trip. Didn’t get to trying the kayaks but the lake is nice and easy to access.

Hot Tub - Walk to the Beach - Mins to Mtns - Lakes
Very clean and cute, small cottage. We had 4 adults was a great weekend for a girls trip. We could have used more bath, kitchen towels. Also a sponge and dish soap were missing. But does have a dishwasher. But over all was a great place to stay and hot tub was great too!

20ft from the Water with Mountain View!
Exactly as per the description. Cute little place right by the water. Stunning location as expected with easy access to kayaks, swimming, fishing etc all of which were fantastic. The place is small, as described, and if you’re tall then manoeuvring up and down the stairs isn’t straightforward especially with luggage - BUT that didn’t affect our enjoyment of the place at all. Would definitely recommend and would return!

RK North : All season Waterfront cottage with dock
A Perfect Waterfront Escape – 5 Stars My wife and I had an unforgettable stay at RK North Waterfront Cottage. From the moment we arrived, we were welcomed by breathtaking views, fresh coastal air, and a sense of peaceful seclusion that made this trip truly special. The cottage itself was spotless, beautifully maintained, and tastefully decorated with cozy touches that made it feel like a true home away from home. We especially loved the spacious deck overlooking the water — perfect for morning coffee or evening wine while watching the sunset. The hosts were thoughtful and responsive, ensuring we had everything we needed without ever being intrusive. Whether it was relaxing by the fire pit, walking along the shore, or just enjoying the tranquility of the surroundings, every moment felt effortless and restorative. If you’re looking for a quiet getaway with charm, comfort, and stunning waterfront views, this is the place. We’re already planning our next visit. — Eric & Juliet DiNoto

Charming Designer Cottage on Marsh
Tiny but beautiful cottage with walls of windows in the living room and bedroom overlooking the salt marsh. It was like staying on a boat! Great kitchen, comfortable bed and cozy fireplace. Beautiful in the winter.

Seasonal lake side cottage
What can I say that hasn’t already been said. This place is a gem. We were the last to book for the year and Tim and Megan made sure that everything was perfect for when we got there. Upon arriving we immediately took the canoe on the lake and caught the last bits of sun. Although it rained for a good portion of our short trip there’s still something magical about having a cup of coffee on the back porch as the rain drops hit the water. 100 percent would come back. Thank you both for sharing this piece of paradise!

🌟Winni Cottage beach, dock, kayaks, SUP & more! 🌈🍸
We had a wonderful weekend at this cottage! The cottage was nice and fit the description exactly. It felt like home! The yard and amenities made it that much better! Kayaks, paddle boards, life jackets, floaties etc. you can’t beat the location when it comes to proximity to downtown Wolfeboro, just a short walk to so many restaurants and stores! Our host was quick with response and very helpful throughout the whole stay! I would highly recommend this place, our family had a very memorable weekend!
Cabin rentals with a kayak

Private Hilltop Cabin, Lakes and Trails Abound..
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!!

Rustic Log Cabin on Pawtuckaway Lake
We had such an incredible stay! The first day was pretty rainy, but the house was so relaxing and comfortable that it didn’t matter - we enjoyed staying in and looking at the gorgeous view of the lake while doing jigsaw puzzles near the fire. When things did clear up, we had a great time playing in the yard snd kayaking. I was surprised at how quiet it was, especially during Memorial Day weekend. The beds were super comfy, kitchen was great, shower and tub were wonderful. Lisa left great instructions and checked in with us to make sure we had everything we needed. And she was very kind in allowing us a late checkout, which was very helpful with three young kids. I can’t wait to visit again!

Little House on the Lake in the Forest
I had a wonderful time staying at Laurel’s cabin! It was incredibly peaceful, with stunning views of the mountains and lake all around. It was the ideal spot for a short vacation! The cabin was spotless and felt genuinely cozy and inviting :)

Thompson Lake, No Cleaning Fee Pine Point Cottage,
wonderful birthday weekend stay. very clean, quiet and peaceful! we had everything we needed to stay busy in the rain! very responsive host

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!

Get away at Crystal Lake
Wonderful Stay in a Great Location! Zak and Emily’s house was exactly as described. It has a fully equipped kitchen, a grill, and a fire pit outside, making it perfect for relaxing evenings. The house is stocked with towels and other essentials, so we had everything we needed. There’s also a ping pong table, which was a lot of fun, and a great collection of movies for entertainment. Check-in was super easy, and the house is conveniently located across from Crystal Lake, offering a peaceful and scenic setting. Communication with Zak and Emily was excellent—they responded quickly and were very accommodating. Overall, it was a fantastic experience, and I would highly recommend staying here for a peaceful getaway. Thanks again, Zak and Emily!

Breezy Moose - A Frame Cabin/ Pet friendly
This beautiful A-Frame was a perfect weekend getaway. My girlfriend and I spent the weekend here and it was in a great location with perfect accommodations for two people. The place was clean with great amenities (grill, fireplace, etc.) Will definitely be hoping to return in the future / am eager to recommend this property to anyone.

Bear Cabin
If I could give 10 stars, I would. First time a place was even better than the photos. Private. Clean. So quiet. Comfortable. Everything we wanted plus ! Felt like we were millions of miles away and a short drive to all attractions. The kayaks, canoe, fire pit and hot tub were used and enjoyed. 3 nights - could’ve stayed way longer ! Don’t hesitate if you’re looking to relax, unwind and enjoy nature. Hands down our new favorite spot and can’t wait to go back ! John and Cassie were very responsive and excellent hosts !
Quick stats about vacation rentals with a kayak in Milton
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ404 before taxes and fees
Total number of reviews
870 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
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- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Sebago Lake
- Squam Lake
- Scarborough Beach
- York Harbor Beach
- North Hampton Beach
- Attitash Mountain Resort
- Story Land
- Weirs Beach
- Long Beach
- Surfside Beach
- Owl's Nest Resort
- Long Sands Beach
- Cranmore Mountain Resort
- Pats Peak Ski Area
- Canobie Lake Park
- Rye North Beach
- Wentworth by the Sea Country Club
- East End Beach
- Purity Spring Resort
- Bear Brook State Park
- King Pine Ski Area