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Vacation rentals with a kayak in Messalonskee Lake and Stream

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Top-rated kayak rentals in Messalonskee Lake and Stream

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Top guest favorite
A charming A-frame cabin is set amidst the lush greenery of the woods. The natural wooden exterior complements the surroundings, while two teal chairs invite guests to relax. A gravel pathway leads to the entrance, framed by large stones and trees casting gentle shadows.
Cabin in Oakland
4.97 out of 5 average rating, 118 reviews

Sister A-Frame in Woods (A)

Escape to one of our two sister A frames. These cozy cottages are nestled in the Oakland, Maine woods. Close proximity to I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. Boating, fishing and ATV riding close by! The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this a perfect getaway for you and your family. Please note some amenities are seasonal. Check out our other listing!

Top guest favorite
The modern A-Frame cabin is nestled among vibrant trees, featuring large glass windows that illuminate the interior with a warm glow. A welcoming deck extends from the entrance, inviting guests to enjoy the surrounding forest ambiance.
Cabin in Chesterville
4.99 out of 5 average rating, 183 reviews

Off-Grid Escape. Wood Fired Hot Tub. 4 Kayaks

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Guest favorite
A comfortable living area features a green sofa paired with a rustic wooden coffee table. Sunlight streams through two large windows, illuminating the light-colored walls and warm wooden floors. An air conditioning unit is mounted on the ceiling, and there is a cozy armchair in the corner.
Home in Liberty
4.88 out of 5 average rating, 103 reviews

Modern Lakefront Home w/ Hot Tub • Winter Escape

Grace's Cottage is a charming 1860's cottage on Lake Saint George. Newly remodeled, the 3 bedroom, 1 bath cottage offers a perfect blend of old-world charm and modern amenities. A spacious screened porch overlooks the lake, and a year-round hot tub provides a perfect spot to relax & unwind. This living space is perfect for gathering with family & friends. Whether you're seeking a romantic getaway or a fun-filled family vacation, Grace's Cottage is the perfect home base for your Maine adventure.

Superhost
A modern tiny house is nestled among tall trees, showcasing two large glass walls that allow sunlight to stream inside. The cabin is elevated on stilts, with a snowy landscape surrounding it, creating a serene and private retreat in nature.
Tiny home in Jay
4.93 out of 5 average rating, 269 reviews

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

Guest favorite
A bright sitting area features large windows offering scenic views of Porter Lake and surrounding mountains. Wooden walls create a cozy atmosphere. A comfortable couch sits adjacent to a flat-screen TV. Nearby, a bookshelf displays a variety of books, enhancing the inviting space.
Cabin in Strong
4.92 out of 5 average rating, 161 reviews

Lakefront Stunning Home, only 35 min to Sugarloaf!

Lakefront Paradise! Fully stocked home on Porter Lake, WiFi, Smart TVs, deck & patio, outdoor furniture, grill, hammock, spacious yard and private dock, swim float, just 35 minutes from Sugarloaf USA's ski slopes, and only 20 minutes from the college town of Farmington's restaurants, bars, shops, and more! Direct access to Maine's best network of ATV & snowmobile trails or ice fishing (winter) out the front door! All the comforts of home, Experience Maine's lake lifestyle at its finest!

Guest favorite
Home in Auburn
4.9 out of 5 average rating, 111 reviews

The Loons' Nest: Lakefront oasis w/ private dock

Welcome to Maine. Enjoy the peace and tranquility of Maines pristine lakes, at our modern Scandinavian lakefront home. On a PRIVATE lake, nestled in the heart of the Maine countryside. This charming retreat offers a peaceful getaway, perfect for those looking to escape the hustle and bustle of city life. The whole group will enjoy easy access to Maines world famous food scene. Enjoy a private dock with stunning views where you can swim, fish, or launch a host-provided kayak or canoe.

Superhost
The glamping Geodome is nestled among snow-covered trees, showcasing a warm glow from its interior. The dome's transparent roof allows for views of the sky, while snow blankets the ground, creating a serene winter landscape.
Dome in Buckfield
4.83 out of 5 average rating, 239 reviews

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

Guest favorite
A studio apartment is illuminated by pendant lights, featuring a queen bed with white linens and a decorative pillow. Wooden walls and floors create a rustic ambiance. A kitchenette is visible along one wall, equipped with basic appliances. The entrance to the apartment is to the left.
Cabin in Whitefield
4.96 out of 5 average rating, 123 reviews

Stella the Studio Apartment

Stella is a cabin-style, pet-friendly studio apartment on 100 acres of wooded property. Enjoy the property's amenities (trails, kayaking, canoeing, axe throwing, wood-fired pizza oven) and return to your comfortable space with a hot tub, power, heat, and plumbing! Stella is located at the start of the land, above our storage building, has plenty of parking and can be reached with 2wd vehicles. This is a new space, exterior is unfinished. The hot tub is an Aqualiving 3 person lounge!

Top guest favorite
An outdoor soaking tub with a white finish is positioned near the water's edge, surrounded by a gravel area. String lights hang overhead, providing soft illumination. A serene view of the lake is visible, framed by lush trees, as evening twilight casts a calming atmosphere.
Cottage in Sidney
4.92 out of 5 average rating, 155 reviews

Waterfront Cottage

The Waterfront Cottage sits directly on the shores of Snow Pond, 15 minutes from Colby College and downtown Waterville and 1/2 mile from the Snow Pond Center for the Arts. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have a private outdoor hot soaking tub and water view barrel sauna. Paradise!

Top guest favorite
The cabin is viewed from the water, framed by lush greenery and tall trees. A spacious porch extends across the front, highlighting the cabin's inviting structure, while the calm water reflects the surrounding nature and the bright exterior of the building.
Cabin in Augusta
5 out of 5 average rating, 105 reviews

Price's Point - Cabin on the water

Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.

Top guest favorite
The cabin entrance features a wooden deck with a railing, leading to a welcoming door. Surrounded by trees, the light filters through the foliage, creating a serene atmosphere. A decorative piece hangs beside the entry, adding character to the exterior.
Cabin in Freedom
4.91 out of 5 average rating, 330 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Guest favorite
A relaxing hot tub is positioned on a wooden deck surrounded by trees, overlooking the serene landscape. A person sits at the edge, holding a glass, with soft sunlight filtering through the foliage, creating a peaceful atmosphere.
Treehouse in Belgrade
5 out of 5 average rating, 130 reviews

SkyView Treehouse | Lakefront • Private Hot Tub

Welcome to your dream treehouse escape — tucked among the pines with stunning lake views, a private hot tub, and direct access to Belgrade Stream. Designed for couples, honeymooners, and small families, SkyView Treehouse offers a luxurious retreat in nature. Enjoy starry nights in the hot tub, cozy evenings by the fireplace, and peaceful mornings on your private deck. Rustic charm meets upscale comfort in this unforgettable lakeside getaway.

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