Family-friendly holiday rentals in Oakland

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.

Camp at Shale Creek Homestead

Stay with us at Shale Creek homestead! No cleaning fee!! Come enjoy the charm of rural Maine! Countless beautiful ponds and lakes minutes away. Spectacular views of the Milky Way on clear nights and much more! Short drives to the Belfast/costal areas and Augusta. A manageable distance from the mountains of western Maine. Beautiful Branch pond at the end of the street. Lake St. George and China Lake under 10 minutes away. A Great location to enjoy Maine Kayak rentals available on site

The Modern Maine Retreat

Stay at our Maine Getaway. Our fully renovated 1940s New Englander is sure to bring you peaceful vibes and luxury. Come play Pickleball with just a quick walk over to the courts, driving not necessary!Close to downtown Waterville, Colby College, Thomas College, UMaine Farmington. 2 min from Messalonskee Lake boat launch where you can boat, kayak, canoe, & ice fish. Proximity to ski mountains, Titcomb, Black Mountain, Sugar Loaf & Sunday River. Please note BBQ is only accessible May-October.

Hilltop Hideaway with Hot Tub & Sauna

Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub or infrared sauna, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

The Rocky Road Camp on East Pond

Welcome to camp life on East Pond. A 1 bedroom home located in Oakland Maine. Your quiet weekend getaway awaits you. Located in central Maine. You will be about a 60 mile drive to the coast or about a 70 foot walk to the lake. Oakland is just a 20 minute drive to Waterville where both Colby and Thomas Colleges are located. East Pond is the host of several area summer camps. The camp will give you beautiful views of the lake. Sit on the deck and enjoy the loons and other lake activity.

The cottage at Marble Farm.

This beautiful private cottage is the perfect place to unwind after a long day of adventure! New, bright and comfortable, this secluded cottage is conveniently located just 40 minutes from Sugarloaf, 50 minutes from Saddleback and 10 minutes to downtown Farmington. Feel free to walk, fat bike or x-country ski on nearly 4 miles of groomed private trails located just outside your front door! Contains a full kitchen for meal prep, as well as high speed internet, and climate control.

Cozy House in Waterville

Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .

Escape and Engage at Bray Barn Farm!

Spacious, quiet carriage house in the Western Maine foothills nestled between farmhouse and barn. 15 acres of gardens, meadows and woods. Great for meandering and wandering about, walking the labyrinth, resting in the shade garden and orchid. Sleeps five. Great for time with family and friends, as well as solitude. We gladly accept persons 21 and older. We welcome children and infants. 4 miles north of Farmington towards Sugarloaf.

Searsmont Studio

Fight inflation with a reasonably priced Maine vacation. Low prices, excellent value. Check our ratings. Peak Foliage Oct. 14-20 Entire studio efficiency apartment w/ private entrance above our garage. Fully furnished, including washer and dryer. Country setting on quiet road. Starlink High Speed WiFi/Satellite TV, full kitchen. gardens, lawns and picnic table. Close to Camden, Rockport and Belfast, but in the country.