
Vacation rentals with a kayak in Greenwood
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Top-rated kayak rentals in Greenwood
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House rentals with a kayak

Birch St - Luxury Lake Home | AC | Swim Dock
Great place next to the lake. Very pristine and peaceful

Our River's Edge Vacation home, Berlin
This home was exactly what we were looking for! The host was amazing! Very prompt at returning messages, instructions were simple yet thorough, would highly recommend!!

Fish Tales Cabin
My husband and I thoroughly enjoyed our 15th wedding anniversary trip to Fish Tales on Moose Pond. It was a bonus that kayaks were there to use. (Saved us from bringing our own for such a far trip) We were looking for peace and quiet from our busy lives and it was wonderful. So quiet! The cabin was clean, comfortable and fit our needs perfectly. The view was magical, as was the sound of the loons in the evening. Sitting around a campfire is good for the soul. We will definitely consider returning for another trip.

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

5br/2ba Lake & Ski House w/ Waterfront & Hot Tub
Stayed here for the weekend with a group of 10 friends and had the best time! Before we arrived, Emily and Anthony sent over a super helpful list of instructions along with recommendations for things to do in the area. They were also really responsive whenever we had questions, which made everything super easy. The location is great with a beautiful water view! While we mostly hung out at the house, we made a grocery run and everything we needed was just 5–10 minutes away. For anyone wanting to explore more, they even had a binder with local recommendations, which was such a thoughtful touch. The house itself is beautiful, clean, and had plenty of room for all of us. We especially loved the bonfire setup and the awesome selection of board games—it made for such a fun and cozy weekend. Would absolutely stay here again!

Kayak to the Causeway-50s cottage with modern vibe
This has been by far the nicest place we have stayed. Super clean and nicely decorated. Wonderful communication by the hosts. Perfect weekend getaway.

Norway Chalet-Lake & SkiRetreat. Game Rm, Hot Tub!
Had a lovely stay enjoying the lake views! There was plenty of sleeping space for everyone and the game room is the perfect place to hangout when the weather doesn’t cooperate. Scott was easy to communicate with and provided ample information about the property. Would definitely stay again!

Water's Edge in Norway, Maine
awesome place to stay for a weekend or a few nights. great getaway with no issues at all. my family will definitely be booking this place again! thank you again Kerry!
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.

Lake Front Cabin on Desirable Highland Lake
My wife and I stayed at John's place for a quick weekend trip but the house is large enough for several more with 5 additional beds plus some space in the living room for sleeping. Great location on the lake with amazing views and only about a mile and a half from downtown Bridgton with some shops and nice restaurants. The house was immaculate and had everything you need from kitchen accessories to towels to plenty of games and books. John was extremely responsive and I don't think I waited more than 30 minutes for the few back and forth messages we had. Definitely recommend!

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.

20ft from the Water with Mountain View!
The cottage was lovely with a fantastic view of the lake. The space was well-appointed and cozy. Lots of greats hikes. Conway has a lot of charm. Highly recommended!

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!

Peaceful Lakeside Maine Retreat
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.

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.

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

Hillbrook Cabin - kayak + hike, steps away!
Took a family trip to see Maine during fall…this lake cabin is a bucket list dream. We enjoyed using the fire pit and also had a blast using the peddle boat on the lake. The fall foilage in October is perfect and staying in Patricia’s cabin is what dreams are made of. Thank you so much for an amazing stay. =)

Charming Lakefront Cabin
This location was absolutely stunning! Brad was incredibly accommodating and even ran over with a high chair after our check out because we had two families with young children. The yard was cute and we loved playing outdoor games in the communal grass area right by the house. The house was very cozy and the perfect space for our families. I wish we stayed longer!

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!

Summah Getaway Lakefront Cabin w/Private Beach!
when we arrived we passed through the front door straight out the back porch door and 30 feet later just gazed across the lake. We knew that instant we were in for an amazing time . Kristin and her husband Dave were great host, don't miss out on this gem when you need to get away from everyday chaos.

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!

Private cabin w hot tub,skiing,firepit & mountains
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!

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.

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 Greenwood
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Sebago Lake
- Sunday River Resort
- Story Land
- Attitash Mountain Resort
- Fox Ridge Golf Club
- Brunswick Golf Club
- Saddleback Ski Mountain Maine
- Mount Washington Cog Railway
- East End Beach
- Cranmore Mountain Resort
- Belgrade Lakes Golf Club
- King Pine Ski Area
- Purity Spring Resort
- Diana's Baths
- Omni Mount Washington Resort
- White Lake State Park
- Sunday River Golf Club
- Portland Museum of Art
- Wildcat Mountain
- Jackson Xc
- Portland Country Club
- Bradbury Mountain State Park
- Wolfe's Neck Woods State Park
- Mount Prospect Ski Tow