Holiday houses in Skowhegan

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Top-rated holiday rentals in Skowhegan

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

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Top Guest favourite
Cabin in Chesterville
5.0 out of 5 average rating, 212 reviews

Off-Grid Cabin with 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- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

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Guest favourite
Apartment in Skowhegan
4.92 out of 5 average rating, 12 reviews

Cute, newly renovated, modern duplex - Unit B

Enjoy a stylish experience at this centrally located space. This is a renovated duplex, created from a little brick schoolhouse built in the early 1900's. It has a tiny home feel. Original, historic maple wood floors mixed with a modern style. Gorgeous windows allow in natural lighting. Loft bedroom, full kitchen, and washer/dryer combo unit. Everything you need for a private night / weekend away. Walking distance to downtown & hospital. Private drive. Best for 1 person CAN fit 3 if small family

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Top Guest favourite
Home in Madison
5.0 out of 5 average rating, 18 reviews

The Shore House

Welcome to your perfect lakeside retreat on the peaceful shores of beautiful Lake Wesserunsett w/ 3 beds/1.5 baths! Main living area has natural wood, cottage ambiance & stunning wall of windows w/ gorgeous lake views. Enjoy private dock, canoe, kayak, 2 decks & large lawn for cornhole. Sleeps 6 w/ king, queen & full beds. Pet-friendly, Wi-Fi, 2 TV's & parking for 4. Mins to breweries, golf, snow trails, theater, skiing, dining & more. Perfect for year-round fun—swim, fish, boat, snowmobile!

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Top Guest favourite
A spacious farmhouse stands amidst a grassy area, illuminated by warm light from numerous windows. A covered porch extends along the front, featuring wooden chairs. The surrounding landscape includes mature trees providing a natural backdrop.
Home in Starks
4.94 out of 5 average rating, 172 reviews

Farm house, River, Island, animals & private Chef.

MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow 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 unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!

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Top Guest favourite
The open-concept living area showcases natural wood walls and a ceiling, with large windows allowing ample light. A soft sofa and a daybed are arranged around a round coffee table on a striped area rug. A staircase leads to the upper level, visible in the background.
Home in Farmington
4.97 out of 5 average rating, 333 reviews

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

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Guest favourite
The kitchen features dark blue walls and modern cabinetry. Granite countertops surround a stainless steel oven and microwave. A double basin sink is present, with a wooden framed chalkboard on the wall and hooks displaying kitchen towels.
Apartment in Skowhegan
4.9 out of 5 average rating, 41 reviews

Apartment in Skowhegan

Located right in town you are within walking distance to several quaint little shops, restaurants bars, and pubs. The newly listed apartment offers 2 bedrooms with 3 beds. Kitchen is nicely equipped! Great place to stay while experiencing activities of Maine. Minutes away from fairgrounds, bounce house, golfing , 4 wheeling/biking/hiking/ITS/xcountry & skiing trails, swimming, rec center, Whitewater rafting, skydiving and a little over an hour to ski areas. Large parking area for trailers.

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Guest favourite
Home in Canaan
4.98 out of 5 average rating, 62 reviews

Dog Friendly | Hot Tub | Lakefront

Escape to Zeus's Landing, a beautifully remodeled 4-season lakefront cottage on Sibley Pond. Nestled in a lakeside community with only four homes, our cottage offers a secluded feel where you can truly disconnect. This Maine retreat comfortably sleeps 6 and features a saltwater hot tub, kayaks, and high-speed Wi-Fi. Enjoy stunning water views from the edge of the lake, a fully stocked kitchen, and beachfront. Perfect for a peaceful getaway with modern comforts and authentic cottage charm.

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Top Guest favourite
Condo in Oakland
5.0 out of 5 average rating, 112 reviews

Home away from home cozy new Apartment in Oakland

Escape to this newly built apartment in Oakland for a relaxing and peaceful getaway. Unwind on the porch while enjoying Maine’s beautiful wildlife, breathtaking sunsets, and star-filled skies. Conveniently located just minutes from Colby College, Thomas College, Snow Pond public beach/boat landing, Bowl in the Pines, and many local restaurants, shops, and outdoor attractions. Perfect for a vacation exploring beautiful Central Maine, visiting family, college visits, or business travel.

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Top Guest favourite
The lakeside cottage features multiple decks, offering expansive outdoor space and views of the surrounding trees. A terraced lawn leads down to the water's edge, where a rocky shoreline can be seen. The building's warm color complements the natural setting.
Home in Belgrade
5.0 out of 5 average rating, 40 reviews

Enjoy a gorgeous sunset steps away from Great Pond

Relax, swim, boat, kayak and enjoy time with your family at beautiful Great Pond Lake. This home is located steps from Great Pond and has 3 lovely decks from which to enjoy the sunset. Great Pond is located only an hour North of Portland in Belgrade Maine. Belgrade Lakes Golf Club is one of the top rated courses in Maine and is a public course. There is easy access to multiple hiking trails. There are also many winter activities - snow shoeing, cross country skiing and ice skating!

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Top Guest favourite
Home in Hartland
4.94 out of 5 average rating, 54 reviews

Waterside Getaway

Come getaway at our waterfront house located in Hartland Maine. This is a perfect spot to unwind and enjoy the peaceful water while relaxing and having fun with your friends and family . A 30 min drive to downtown Waterville where you can find shopping and dining places for the whole family . Enjoy fishing , swimming and more right outside your door . The house also has a boat launch and dock for your boat if you choose to bring one. We hope you enjoy staying at our home.

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Top Guest favourite
The exterior of the house is presented, featuring a green metal roof and a large driveway leading to a two-car garage. Lush green grass surrounds the home, while trees and a clear blue sky enhance the peaceful rural atmosphere.
Home in Cornville
4.98 out of 5 average rating, 50 reviews

Modern Cornville Ranch

Escape to peaceful Cornville and relax at our newly renovated house. Our house features a new kitchen, stylish furniture, and a luxurious primary suite with a king-size bed and private bathroom. The second bedroom offers 2 full-sized beds. Stay connected with high-speed internet and TVs in every room. Conveniently located just 10 minutes from Skowhegan, close to ATV and snowmobile trails, and only an hour away from Sugarloaf ski resort, Greenville, Augusta, and Bangor.

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Guest favourite
The cabin's exterior is framed by lush green foliage, showcasing a welcoming wooden porch with steps leading up to the entrance. The log cabin features large windows and a combination of wood and lattice detailing on the lower level, surrounded by a serene natural setting.
Cabin in Madison
4.94 out of 5 average rating, 34 reviews

Grace Landing

In the heart of central Maine our charming, secluded cabin is nestled on a peaceful dirt road. This spacious home offers 4 cozy bedrooms and 2.5 bathrooms, making it perfect for families or groups of friends. Whether you’re looking to relax by the fireplace, enjoy the serenity of the surrounding woods, or explore the nearby lakes and trails, our cabin has everything you need for a memorable stay.

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Popular amenities for Skowhegan holiday rentals