Holiday rentals in Messalonskee Lake and Stream

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Top-rated holiday rentals in Messalonskee Lake and Stream

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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, 190 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)

Top guest favourite
A circle of white Adirondack chairs is arranged around a fire pit on a manicured lawn. Tall trees provide shade, and a serene lake is visible in the background, reflecting the soft light of the evening. The scene conveys a peaceful outdoor gathering space.
Home in Oakland
4.99 out of 5 average rating, 84 reviews

Lakefront 3 bedroom pet friendly on Messalonski

Make memories of a lifetime at this unique and cozy family-pet-friendly private lakefront on Messalonskee. Beautifully manicured lawn/gardens with a fire pit surrounded by the peaceful sounds of nature. A large dock to take in the spectacular views of bald eagles, loons, and blue herons. Owners boat is attached for occasional boat rides. This guesthouse is newly built with a covered porch overlooking the serene lake. Comes w/3 kayaks, 2 paddle boards, a paddle boat, life jackets, and a canoe

Top guest favourite
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
4.98 out of 5 average rating, 132 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. Check out our other listings managed by Hall’s Homes RE online!

Top guest favourite
The guest cottage features a warm yellow exterior complemented by green trim. A small porch with a green chair invites relaxation amidst the surrounding trees and fallen leaves. The structure showcases a single door with a window, offering a glimpse of the peaceful wooded environment.
Tiny home in Belgrade
4.99 out of 5 average rating, 79 reviews

epicurean feast with zen like surroundings

My sister and i will welcome you to our guest cottage on a quiet lake in Belgrade. We are including a dropped off gourmet breakfast-you pick the time, between 7:30 and 9:00. We include waterfront access as well as use of a kayak. We are located on a beautiful lake in the middle of the woods. Peaceful and absolulely quiet. We will practice extreme sanitation as well as social distancing. One well behaved dog is welcome as long as they are not left alone in the cottage- dog bed supplied.

Guest favourite
A serene outdoor area is framed by lush greenery and trees, showcasing vibrant orange flowers in the foreground. A meandering stone path leads towards a gathering area in the distance, partially visible through the foliage.
Home in Sidney
4.87 out of 5 average rating, 112 reviews

Brook Ridge Retreat

Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.

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, 439 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 does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top guest favourite
Farm stay in Oakland
5 out of 5 average rating, 17 reviews

Cozy Maine Farm Retreat w/pool & dog friendly

Offering 3 Bedrooms, 2+ bathrooms, fully stocked kitchen, pool and fire pit — your Belgrade Lakes farmhouse getaway just an easy 15 minutes to Waterville and Colby College. Enjoy sunny afternoons by the pool, boating or kayaking is just a short 5-minute drive to Messalonskee Lake. Relax in the evenings around the fire pit. Fully stocked kitchen, peaceful country setting, and the perfect mix of comfort and convenience. Summer dates fill quickly — book early!

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
4.82 out of 5 average rating, 122 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.

Top guest favourite
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, 110 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.

Guest favourite
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, 132 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.

Top guest favourite
A spacious two-story home is showcased amidst a snowy landscape. Snow covers the roof and ground, while evergreen trees flank the entrance. Festive decorations accent the front door, and a gentle snowfall creates a serene atmosphere on the property.
Guest suite in Oakland
4.98 out of 5 average rating, 256 reviews

Cozy Studio Flat, Belgrade Lakes Region

Kick back and relax in this calm, stylish, newly renovated second floor space over the garage. Enjoy four seasons in the Belgrade Lakes region of Central Maine. Hunting, fishing, hiking, biking, skiing, and snowmobiling, to name a few of the many activities available. We are 2 miles from Oakland Waterfront Park on Messalonskee Lake and just over an hour drive from both beaches and ski resorts.

Top guest favourite
An open-concept kitchen and living space features exposed wooden beams and a sleek black stove. Green cabinetry complements the stainless steel appliances. Two bar stools are positioned at the kitchen island, while a cozy sitting area overlooks the wooded surroundings through large windows.
Tiny home in Freeport
4.99 out of 5 average rating, 368 reviews

Cozy Rock Cabin #thewaylifeshouldbe

*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire. Follow the journey on IG at @cozyrockcabin!

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