
Holiday rentals with a kayak in Winthrop
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Top-rated rentals with kayak in Winthrop
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.
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Popular amenities for kayak rentals in Winthrop
House rentals with a kayak

Sugarmaple Lakehouse - Sebasticook Lake Newport ME
Great location. Woke up to the sounds of birds. very responsive. I would have given it a 5 star all the way, David was amazing and responded in a very timely manner. But, the turn over service could have been much better. The previous guest left a wine bottle in the automatic fridge ice dispenser and it was unfounded until my family found a large peice of glass in their drink, serious hazard to drink glass. Should have been spotted by the turn over service but, who would check the ice maker for a bottle a wine? I understand that. Very uncommon and unfortunate for us. David responded in a very fast manner and gave us options to accommodate the situation. I would have left a 5 star if this was the only thing but everything was so unorganized in the kitchen, they had everything but nothing made sense to why it was there. Sink didn't drain. There were also stains on the sheets and a pizza box left by the fridge that wasn't ours. Little things but the turn over service was a let down.

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!

Waterfront Gem walkable to Restaurants!
It’s very cute little house. We’re enjoy it. Thank you so much.

Lakefront summer getaway cabin for 6
We had a great week at the cabin! The view is amazing and it was so relaxing. Courtney was very responsive and attentive. Highly recommend for a cozy getaway in a beautiful setting.

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Great rental property in a great place.

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!

Waterfront Farmhouse with Modern Flair!
We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba
My wife and I completely enjoyed our stay at Ani’s place. She literally thought of everything any guest could ever want. Beautiful surroundings…walking distance to the Fish Ladder….a couple of miles to all the restaurants downtown. And the place itself is immaculate. The kitchen was perfect for eating in every night. This place is an absolute no-brainer to rent and we can’t wait to return!!!
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.

20ft from the Water with Mountain View!
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!

Hidden Haven A Rustic Retreat In St. George, Maine
Really enjoyed our stay at the cottage. Everything was clean and cozy. Great time going through the DVDs, board games, and close access to Rockland town. This was an amazing stay and one for the scrap books!

Cozy waterfront home on Merrymeeting Bay.
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 :)

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.

Peaceful Cottage on Maine Flower Farm
Perfect fall cottage so close to Portland! The cottage is so peaceful and quiet. But so close to Portland but you wouldn’t even know it. The farm is lovely and we took a walk down to the river on the property, it was so peaceful and so much land! If you are looking for a get away from a city, but want to be able to explore Portland and Kennybunks, this was the perfect spot. I don’t know if I’ve slept that good all year. Would definitely come back again. And we love Trooper the dog!

Lakefront, Beach Private, Amazing Views, & pets!
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

Lakefront Stunning Home, just 35 min to Sugarloaf!
Absolutely beautiful views. Peaceful location. House is very well equipped with board games and basic amenities!

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

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

The Conscious Cabin
Does the cabin look perfect in the photo? It's better. Does the yard look like the perfect place to forget the rest of the world exists? It is. Are the White Mountains a place that make you feel like the psychological mountains in your life are just a little smaller? They are. We don't have enough good things to say about the Cabin or communicating with Cassouki. It's rare to step into a space that feels like it was designed with intention on every level - from the scents in the air to the textures of the cabin to the quiet confidence in every object's placement. The Conscious Cabin doesn't just reflect a designers eye, it reflects a storyteller's heart. I've stayed in more than a few retreats, but this is the first one that felt like it had something to say--and somehow said it quietly enough to let us hear ourselves again. Stay here.

Smitten - you will be - Hear Silence.
such a peaceful, charming place. total privacy and very clean, would definitely stay again

Mill Pond Waterfront Cabin On The Way To Sugarloaf
very much worth the money to stay, Farmington is a beautiful town and the cabin is gorgeous with the view onto mill pond.

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)
We celebrated our 25th wedding anniversary at this charming camp on Webb Lake, and it was everything we hoped for and more. The serene setting was perfect for enjoying the outdoors together. We spent our time fishing on the beautiful lake, where we caught a handful of fish. Kayaking was a highlight as well; the combination of being on the lake, mountain views and beautiful weather was simply magical. The camp itself was cozy and well-equipped, providing a wonderful weekend getaway. If you're looking for a peaceful getaway filled with outdoor fall activities, this is the place to be. We left already planning out next trip back. Thank you for sharing your home.

Riverfront cabin between Portland & White Mtns.
Very cozy cabin, easy for multiple people to stay in. Great atmosphere with inside and outside speakers, a beautiful river, and a great fire pit location. Highly recommend staying here.
Quick stats about holiday rentals with a kayak in Winthrop
Total rentals
20 properties
Nightly prices starting at
₹7,707 before taxes and fees
Total number of reviews
920 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Sebago Lake
- Sunday River Resort
- Popham Beach State Park
- Pemaquid Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Coastal Maine Botanical Gardens
- Samoset Resort
- East End Beach
- Belgrade Lakes Golf Club
- Cliff House Beach
- Pemaquid Point Lighthouse
- Sunday River Golf Club
- Portland Museum of Art
- Maine Maritime Museum
- Portland Country Club
- Bradbury Mountain State Park
- Wolfe's Neck Woods State Park
- Eaton Mountain Ski Resort
- Pinnacle Park
- Rockland Breakwater Light
- Lost Valley Ski Area
- Head Beach
- Pebbly Beach