
Vacation rentals with a kayak in Woodstock
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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 thoroughly enjoyed our stay at Sebago Lake. The area is stunning, with nice access to the water, making it a perfect spot for exploring the surroundings. Colleen and Leo were incredibly responsive and welcoming, ensuring we felt right at home. We would absolutely choose to stay here again!

Rising Tide Times - quintessential Maine cottage
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.

Waterfront Gem walkable to Restaurants!
Beautiful house on the pond! Perfect for our family of 4. It was comfortable and relaxing. Amy is a wonderful host! She checked in and made sure we had everything we needed. We really enjoyed our stay! Hoping to stay again sometime.

Lakehouse with 100ft of private waterfront
My wife and I spent our first year anniversary in this wonderful home. We had a great time enjoying the fall colors and over looking the beautiful pond, especially in the morning as the fog broke. Within 15 minutes there were several grocery shopping options, restaurants, and breweries. Perfect balance of being in a quiet setting but having amenities nearby. Would recommend and hope to go back next autumn!

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!

Kayak to the Causeway-50s cottage with modern vibe
We stayed for 4 nights and enjoyed them all. It’s very peaceful and quiet and we enjoyed the short walk to the lake. There was many board and card games which we enjoyed playing. Our hosts were extremely kind and attentive! The local guide book was very helpful as well! We were arriving late for check in so they made sure the heat was going for us so we could go right to bed! Would definitely book again if we come back to the area!

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.
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.

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!
Such a beautiful and cozy stay! literally feet from the water. It was incredible to wake up to that view. A cozy cabin feel with modern amenities. such a great space! thank you for having us

Waterfront Cricket Cottage Pleasant Pond Turner ME
We had a wonderful and peaceful stay at the cottage. The location was perfect for a relaxing getaway surrounded by nature and offering stunning sunset views of the pond along with kayaks to go out and enjoy! The cottage itself was cozy and clean and we felt at home! Darlene was welcoming and attentive ensuring everything was just right for our stay! I highly recommend this charming retreat for anyone looking for a peaceful stay! It was a bit chilly so we were able to enjoy the fire pit outdoors with the wood that was provided! I can’t wait to return and stay longer! We can clearly see why this cottage has so many positive reviews!!

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.

Peace at the Pond with Hot Tub & Sauna
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!

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!
My boyfriend and I had an outstanding time at Helens cozy spot. We spent all day kayaking and canoeing in the beautiful lake. We absolutely loved this home and will miss it dearly. We'll hopefully be back another time. The dishwasher amenity was a life saver! We also hiked up Mount Willard via Crawford's notch (much to my surprise my boyfriend proposed up there!) This will be a get away I will never forget. Definitely stay at this lovely lake house.
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, No Cleaning Fee 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
This is a beautiful home that is very well maintained and cared for. Alexa's cabin was a great place for 5 of us to gather, relax, and enjoy. Kitchen has everything you need, the hot tub is fantastic during a spring snowstorm, the beds were very comfortable, and it provided ample space for us.

Mill Pond Waterfront Cabin On The Way To Sugarloaf
4 of us stayed at this cute little cabin. Exactly as depicted and many helpful amenities were left for us to use such as seasonings, ice, and some wood. Pretty and quiet place to get away.

Bear Cabin
The cabin was so beautiful and peaceful. The area wasn't too far from everything, location amazing. It was very quiet and just what we needed to reset. I definitely recommend if you are looking to get away and want to be close to North Conway. The pictures were exactly what you will see when you get there. Absolutely no complaints on our stay at the cabin. We enjoyed the pool table, the dart board and hot tub. We didn't get to light a fire outside which would have been nice but we ran out of time, still very much enjoyed the area. Friendly neighbors while driving through the road.

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.
What a beautiful thoughtful place! There were games to enjoy, a kayak, a wood stove inside, and fire pit outside. This place was such a beautiful gem!
Quick stats about vacation rentals with a kayak in Woodstock
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees
Total number of reviews
1.4K 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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- Sunday River Resort
- Attitash Mountain Resort
- Saddleback Ski Mountain Maine
- Story Land
- Cranmore Mountain Resort
- Wildcat Mountain
- Fox Ridge Golf Club
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