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

Sebago Lake, ME *Lakeside*Hot Tub* just renovated
We just loved staying at Colleen and Leo’s home. It was in a beautiful location and stocked with everything we could ever need. The home was clean and check in/out was a simple process. They were responsive to all my messages and overall great hosts! Would definitely recommend a stay here!

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!

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim
The place is clearly well taken care of with attention to detail. This would be a great place any time of year. Miriam and the home were very accommodating. I would return to this location with great peace of mind.

In the Trees - NH w/ Lake Access
Absolutely phenomenal location! Would definitely recommend if you need a little reset and relaxation, hope to return again soon

Peaceful River House - 20 minutes from Portland!
We loved our stay at Wendy's place. The location is perfect on the river & close to Portland so it was the best of both worlds. Wendy couldn't have been any more accommodating, offering us early check in and a late check out. She was easy to communicate with & ensured we had a seamless experience. The house was exactly what we were looking for. We hope to visit again in the summertime!!!

Lakefront Retreat! Dog Friendly!
This lake house was beautiful and the view is stunning! Every room is well appointed and perfect for setting a lake vacation vibe. The house has everything you could need. The description and pics on Airbnb are thorough and completely accurate. Jenna was an awesome host - very responsive and helpful and flexible. We will definitely be back!

The lake at your back door!
Irene was a great host! She reached out with very helpful information regarding the property and lake, which allowed us to prepare well for our stay. The house was clean, well-stocked, and exactly as pictured—perfect for a vacation getaway with friends!

Charming 4 bedroom lake front, with private beach
Amazing play for a family vacation. My little one loved the beach area and all the toys.
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!
This place offered exactly the peace and quiet that I was looking for. I booked this place for my boyfriend who needed some alone time to focus on school work and his keep his mind away from a stressful job. The house is very comfortable, quiet and great view. The bathroom is a bit tight and toilet is too low. But the host still managed to make it cozy for grooming. They also provided toiletries for both men/woman which is a plus, because we women over-pack or forget to pack the unexpected feminine essentials! :) Everything you see un the pictures is as shown or described. the kitchen is also equipped with some cooking spices and everything you need to cook a meal. I would definitely book here again but next time, Im coming along for my peace and quiet!

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.

Lakeside Bliss, Cook’s Kitchen, 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!

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.

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!
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!!

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub
My friends and I had a great time relaxing at this beautiful place. Aqeel and Michelle were extremely responsive and helpful when necessary. We would stay again!

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
great cabin & very spacious. Hot tub was a great amenity - Alexa was great with communication. Would highly recommend!!

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 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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- Sunday River Resort
- Attitash Mountain Resort
- Saddleback Ski Mountain Maine
- Cranmore Mountain Resort
- Story Land
- East End Beach
- Wildcat Mountain
- Fox Ridge Golf Club
- Brunswick Golf Club
- Mt. Abram
- Purity Spring Resort
- King Pine Ski Area
- Belgrade Lakes Golf Club
- Mount Washington Cog Railway
- Omni Mount Washington Resort
- Diana's Baths
- Jackson Xc
- Portland Museum of Art
- Waterville Valley Resort
- Mount Prospect Ski Tow
- White Lake State Park
- Echo Lake State Park
- Black Mountain of Maine
- Conway Scenic Railroad