Holiday rentals with a kayak in Messalonskee Lake

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Top-rated Accommodation with a Kayak in Messalonskee Lake

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Top Guest favourite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 404 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top Guest favourite
Cabin in Chesterville
5 out of 5 average rating, 160 reviews

Off-Grid A-Frame - Peaceful w/ Wood Fired Hot Tub

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 favourite
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
4.94 out of 5 average rating, 253 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 $150.

Guest favourite
A spacious dome tent is nestled among tall trees, with sunlight filtering through the leaves, creating a warm glow. The forest floor is covered with soft earth and scattered leaves, enhancing the natural surroundings, while the calm ambiance invites visitors to relax and enjoy the scenery.
Island in Monmouth
4.97 out of 5 average rating, 254 reviews

Hammock Haven Island Dome

The Hammock Haven Island Dome looks at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals, hammock nap on a dock in the water, bask in the glow of the fire or wood stove, hear the calls of the loons, play on the rope swing, canoe, kayak, or paddle board the lake, and explore the trails of this 14 acre wooded island, and then repeat as needed. We greet you at our shoreside dock and help you settle into island-life. Enjoy super clean, Superhost, Maine Guide hospitality.

Top Guest favourite
A spacious farmhouse exterior is illuminated by warm lights against the evening sky. The porch features several wooden chairs, inviting relaxation. Large windows reveal the welcoming interior, surrounded by lush greenery.
Home in Starks
4.93 out of 5 average rating, 145 reviews

Fall in Maine! Farm Stay with River.

Medicine Hill is a 125 acre farm on the Sandy river complete with an old fashioned swimming hole and an entire island to explore. We grow a wide variety of vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch taking it all in. 4 bedrooms have incredible views and are surrounded by trees or fields. And if the Chef is available..eat!

Top Guest favourite
Home in Oxford
5 out of 5 average rating, 219 reviews

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Top Guest favourite
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
4.95 out of 5 average rating, 102 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!

Guest favourite
An airy cabin interior features wood beams and a large sliding glass door, providing access to a deck and surrounding greenery. A small dining area with a table and two chairs is visible alongside a well-equipped kitchen area, complete with modern appliances.
Tiny home in Bowdoinham
4.9 out of 5 average rating, 136 reviews

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

Top Guest favourite
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 favourite
A serene landscape captures a vibrant sunset reflected on calm water. The sky displays shades of orange and pink, blending into deep purple hues, while the silhouette of trees lines the horizon. The tranquil scene conveys a peaceful natural setting.
Loft in West Gardiner
4.97 out of 5 average rating, 209 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment above our garage. 15 minutes to Gardiner/Augusta, 15 minutes to I95/295. Less than one hour from Portland. Sit by the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and play. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Guest favourite
A serene lakeside scene features a blue canoe resting on sandy shores, with a solitary blue adirondack chair positioned nearby. The calm water reflects the surrounding trees, creating a peaceful connection with nature.
Chalet in Belgrade
4.98 out of 5 average rating, 114 reviews

Sunset Chalet Lakefront Hot Tub Game Room

Tucked along the peaceful shore of Belgrade Stream, Sunset Chalet is a private, waterfront escape designed for cozy connection and quiet joy. With a hot tub beneath the trees, a warm fire flickering inside, and a playful game room downstairs, it’s the perfect space to unwind and make memories. Whether you’re celebrating a honeymoon, anniversary, or enjoying a relaxed family getaway, Sunset Chalet offers a setting that feels both special and deeply comforting.

Guest favourite
A serene lakeside view reveals calm waters reflecting the sky. Pine trees frame the scene, with a wooden railing suggesting a deck area. The landscape is peaceful, featuring a distant tree-lined shore under a clear blue sky.
Chalet in Belgrade
4.81 out of 5 average rating, 121 reviews

Visit Beautiful Home on Snow Pond

Belgrade Lakes, Maine's premiere lakes region. Beautiful, four season home on 9 mile long, Messalonskee Lake also known as, Snow Pond. Come to experience life the way it should be. Sunrise view, from master bedroom and lakeside deck surrounded by undeveloped wooded shoreline. Swim, canoe and kayak from private dock. Loons, eagles, osprey, and beavers can be your neighbors for a relaxing week at the lake. Open concept kitchen dinning and living room.

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