Holiday houses in Oakland

Off-Grid w/ Wood Fired Hot Tub - 4 Kayaks Included

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)

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

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.

Sister A-Frame in Woods (A)

Escape to one of our two sister A frames. This cozy cottages are nestled in the Oakland, Maine woods. Close proximity to major Route I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this A frame a perfect getaway for you and your family. Please note some amenities are seasonal. Feel free to check out our other listings!

The heart of the Belgrade lakes

Located in a quiet country setting just minutes from the Oakland boat launch and McGrath pond, this place is stocked for your convenience with a coffee/tea/cocoa bar, air fryer, and full kitchen. Washer and dryer in unit. Swing set, sand box, and trampoline out back. A short drive to downtown Waterville for shopping and entertainment. A 15 minute drive will take you to Maine General, Colby college, or Belgrade lakes. 20 minutes to Augusta. Owners on property to accommodate your needs.

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.

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.

Kate-Ah-Den Cabin, a soul soothing escape.

Secluded & artistically built - a cozy cabin on top of Hampshire Hill. Relax and enjoy the views, take time to hear yourself think, or go explore 75 acres of private woods w 2 miles of private trails. 10 minutes from downtown Belgrade Lakes & public beaches on Long Pond & Great Pond. Close to Kennebec trails, snowmobile trails, Farmington & Augusta. 1 hr south of ski resorts. Great for stopping for 1 night or for taking a week to escape from the world.

Ultra Spacious and Hosts are Gracious

Enjoy easy access to everything from this centrally located 3 bedroom/2.5 bath home. Newly renovated, very spacious sunlit home only 2 miles from I-95, public beach 1 mile, Colby College 6 miles, Thomas College 3 miles, Waterville 3 miles, Augusta 15 miles, and in the heart of the Belgrade Lakes chain. Many food options in all directions. Clean, comfortable, open, bright, and includes a private yard. This home sleeps up to 6 guests with its 3 queen beds.