
Vacation rentals with a kayak in Greenwood
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House rentals with a kayak

The Cliff House
Extremely peaceful and relaxing! The rental is more like a home than a cottage/camp with its recent tasteful, pleasing, and very functional renovations (the flooring was well done and looked great; the mini-split system made it very comfortable even when it was in the 90’s; and, the new furnishings were attractive and comfortable). We thoroughly enjoyed ourselves!

Sebago Lake, ME *Lakeside*Hot Tub* just renovated
We had a great stay at Colleen's home. The pictures didn't do the house justice. We arrived right after a snowstorm and the property was plowed and shoveled for our arrival. They were very proactive in letting us know how the roads were. Having the hottub in the winter and being in a quiet neighborhood was just what we needed. We'll definitely book again!

Waterfront Gem walkable to Restaurants!
My family and I loved Amy’s place. The kids got to go on the lake and sled down the side of the house was super neat. Was close to everything too.

Beautiful lake-side home close to Portland Maine
Claire and Karen's home was the perfect destination for our Christmas gathering. The house was super clean and well equipped with anything a guest could need. The three story living worked well with adult children and the open layout was great for cooking, eating and spending time as a group. A detailed "welcome book" provided local recommendations which was greatly appreciated and made our arrival and departure a breeze. It was a beautiful setting with extra touches that made it feel warm and inviting. I highly recommend this property and want to thank both Claire and Karen for making our holiday special and sharing their beautiful home!

The Lake House
Such a memorable winter visit to Windham! This property is the third of Dianna’s that we’ve stayed at, and just like the others, it met our needs perfectly. From the moment we arrived, we felt comfortable and at home; the house had all the amenities and appliances we needed (and beyond)! The neighborhood is welcoming and so conveniently located near Portland, but it's also a peaceful retreat from the city with the lake house vibe and beautiful view. Dianna is a responsive and accommodating host, and she has such thoughtful touches and decor throughout the property. We can’t wait to return to the lake!

Lake House in Brownfield near North Conway NH
This space was cozy, inviting, and felt like home. The fireplace made the living room the spot to be. Walking to the pond and looking out was calming as was waking up to water views and a warm coffee was fantastic.

Waterview Lake House
Beautiful spot! Far enough from everything to feel private and peaceful but not so far that it's inconvenient. Nice and clean. Would stay here again.

Maine Lake Escape* Hot Tub*
Great cabin! Remote and beautiful. Hot tub was lovely. James was communicative and his folks took care of snow plowing right away after a storm. Would definitely stay again.
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.

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug
My husband and I spent 6 days here for our anniversary. I wanted a location on the water and close to visit all the major coastal towns in Maine. This was perfect! The home, felt like home, and everything was clean and beautiful. Adam was very helpful whenever I had any questions. Sipping coffee every morning on the back porch and watching the sunrise over the lake was so peaceful. Grocery store close by and great hiking/walking areas right out the front door. Can’t wait to come back and bring the family.

Nay'tures Cottage
The cottage was so beautiful, clean and cozy. Tom and Rosemarie gave us tips on places to go to try to see moose and avoid the crowds near the touristic places. Kitchen was fully equipped and everything worked just as expected. I just wish we had come in a hotter day so we could use the kayak and paddles on the lake! Will definitely come back!

20ft from the Water with Mountain View!
Great place close to all the favorite locations.quick response time. easy going. Great place! will be back asap

Loons Rest – Maine Quintessential Cottage
Loons Rest was the perfect get away spot for our 40th anniversary. We were lucky to enjoy the swimming dock in mid September as the daytime temperatures were in the upper 70's to low 80's. The lake was pristine and was warm enough for swimming still. We enjoyed watching and hearing the loons as well as the eagles and kingfishers. We loved the outdoor fire pit when the evenings turned cool as well as the indoor fireplace which is a work of art! Also the was plenty of well seasoned firewood. Everything about this place is very well thought out. If they don't have it you don't need it! The kitchen was well equipped and we were happy to find that there was everything we needed to prepare pizzas to cook on our solo stove pizza oven that we had brought along! John is a great host and responded quickly to any questions we had. Would highly recommend Loons Rest to anyone who is looking for a peaceful and relaxing spot to vacation.

Private Cottage on Lake, Sauna & Hot Tub, Dogs OK
Wonderful,private, well equipped cottage on pretty pond. Owners quick to respond to our texts. Relaxing hot tub and fantastic sauna! Many restaurants and breweries within a 30 minute drive. Book it ..... you won't wanna leave!

Covered Bridge Cottage - Maine woods and river
From arriving to the hospitality throughout the stay to check out everything was just amazing!! Hidden gem for sure! Very relaxing cottage with a beautiful view. Very cozy, felt right at home. I used to live in Maine so returning for NYE and my daughter’s birthday and experiencing this after the fast pace living in Miami was an amazing experience, just what I needed!

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.
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!!

Thompson Lake, Spring discount. Pine Point Cottage
The cabin was very quaint and cozy for a snowy day. A quick walk to the lake and not too far from some cute shops and restaurants in Norway. Very responsive and friendly hosts. Incredibly clean and well maintained. Would stay again!

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
My friends and I had a wonderful weekend. We loved the fire place, whirlpool with lights and watching the stars and of course the surroundings. We went for a walk on the lake! Can only recommend that place.

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.
The place was beautiful and so peaceful. The cabin was cozy, clean and had everything we needed. Teresa was great with communication and giving us recommendations. We are already thinking of coming back.

Maine Lakes-Pleasant Mt-Private Trails
Didn’t stay there, but he was nice enough to refund me my money back due to a breakdown on my vehicle. It’s the reason why I did not stay.

Lake Front with Private Dock - BRAND NEW Furniture
We recently stayed at Darryl's Lake front property. The house was beautiful and very well stocked. We enjoyed the open space concept and the beautiful snowy, lake view. Darryl's instructions for locating the property were easy and the house included everything that was listed. Darryl was quick to respond when I had messaged him and even provided suggestions for dinner nearby. I would definitely recommend this property.
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
1.3K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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