Holiday houses in Oakland

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)

Quaint Little Cottage

Clean, quiet, cozy, and includes extras that will make your stay a comfortable one. We host short or long term. Located in the Belgrade Lakes region this home is nearby Colby and Thomas College, Maine General Hospital, centrally located between Waterville and Augusta, and 1 hour to the Maine coast as well as ski mountains. Enjoy hiking, fishing, exploring Maine, and more! For great dining options your commute is 5-10 minutes, or you can stay in and have delivery from one of our local eateries.

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!

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.

The Lake House on McGrath Pond | 4BR | Waterfront

Unwind year-round at this stunning lakeside home on McGrath Pond with 100+ ft of private water frontage. Sleeps 10 with 4 spacious bedrooms. Enjoy an open floor plan, fully equipped kitchen, large deck with lake views, WiFi & cable TV. Near Colby College and a short drive to Sugarloaf, Acadia, Bar Harbor & Freeport (LL Bean and outlets). Whether you're kayaking in summer, leaf-peeping in fall, or skiing in winter, this home has everything you need for a memorable Maine escape.

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!

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.

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.

Lake-House on water, East Lake, Near Waterville

Welcome to the Lake House! 5 bedrooms. Access to a mooring. Full bathroom and kitchen with accessories. Bedrooms have locked doors & Wi-Fi. The house has a Deck and Docks, 8 foot by 10 foot floating Island, BBQ Grill. Lakeside Bon Fire Pit. Full bath, 30 feet from Lake! 2 entrances, 3 Kayaks, Fishing/Swimming. Nice neighbors including Camp Manitou, Matoaka and Somerset. Near Public Boat Landing & country store. I reside nearby, and will help with any issues.

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Classy AF Home, walk across the street to Colby!

THE BOOKING CALENDAR OPENS ONE YEAR IN ADVANCE, INCLUDING GRAD WEEKEND. Lovingly renovated three bedroom home across the street from Colby College’s Senior Drive. My grandfather built our house in the 40’s, we have done all of the renovations ourselves to create open, inviting spaces with unique touches while maintaining the original footprint. Our home is a labor of love that we hope YOU love. *Pets ok w/ notice and 50$ fee*

Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets

Escape to our peaceful East Pond lake retreat—where slow mornings, sunset views, and loon calls set the tone for your stay. 🌅 Shared water access + stunning sunsets 🚣 Complimentary kayaks & canoe 🔥 Fire pit, outdoor dining & relaxing lake vibes 🐾 Pet-friendly for your four-legged family members Now offering flexible summer stays—no full-week commitment required. Perfect for long weekends or midweek getaways.