Holiday rentals in Skowhegan

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

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!

Cottage That Overlooks The Field

Discover The Cottage that Overlooks the Field—a unique Maine retreat blending New England charm, modern comfort, and inspiring natural beauty. Celebrate milestones, reconnect with friends, or find peaceful solitude while experiencing the true essence of Maine—its landscapes, fresh local flavors, and rich cultural traditions. This soulful space invites you to slow down, awaken your creativity, romanticize everyday moments, and leave deeply refreshed, inspired, and connected to life’s simple joys.

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!!!

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.

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.

Bear Cub Lodge

Nestled in Starks, Maine, this rustic-modern log cabin offers a serene retreat. Primarily crafted from trees on the property, This brand new build boasts a handcrafted log exterior and modern interior comforts. Large windows, a crackling fireplace, and a spacious kitchen invite relaxation. Outside, a sprawling covered deck offers stunning views. Whether for a peaceful escape or outdoor adventures, this cabin strikes the perfect balance of rustic allure and modern convenience.

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.

Halcyon Ridge

Halcyon Ridge is owned by Lynn & Chuck Hadyniak, who live nearby. Lynn & Chuck moved out of New Jersey years ago to get away from the hustle & bustle, & raise a family in peace. They love Freedom for its quiet & natural beauty, & would love to host people at Halcyon Ridge who also want to escape the noise. Stargazers will be delighted: low humidity, expansive view of the southeastern sky, & next to no light pollution, make for wonderful viewing. Rest. Relax. Recharge.

Charlie's Perch -Charming Lakewood Cottage

Nestled in the historic Lakewood Community sits our waterfront home. Walk out of your bedroom door onto a custom deck overlooking Lake Wesserunsett. Enjoy sunsets and tranquil sunrises under the pavilion. Plan your day around fishing, swimming, boating and all the adventures Maine has to offer. Use of the lake is at your own risk and liability. By booking you and all of your quests hold harmless the host and resident of the lake. There is no life guard on duty.

Former Hydro Station

Beautifully converted hydro station on the banks of the Sandy River in Norridgewock Maine. The serene open space features nine large windows with views of the river and surrounding cornfields. Perfect for artists, writers, musicians, chefs... Rustic yet thoughtfully designed– the home has received a preservation award as well as features in magazines such as Down East, Dwell, and Waves & Woods.

Home away from home

Skowhegan, Maine is centrally located to everything. It offers both a vibrant and unique downtown with close proximity to outdoor recreational areas. The Kennebec River runs through Skowhegan’s charming downtown area, and the town is easy to navigate. Pedestrian friendly sidewalks, downtown green spaces, and beautiful facades are worth the trip. Skowhegan has something for everyone.