Holiday rentals in Oakland

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.

Lakefront home w/Dock & Fire Pit + Pet Friendly

Nestled right on the picturesque McGrath Pond, this cozy retreat is perfect for you and your loved ones. The back deck is perfect for BBQs or end your day around the fire pit! Enjoy 100' of your own private lakefront where you can canoe, kayak or keep a smaller boat at your own dock in this protected shallow cove. Explore the 7 miles of shoreline or check out Ellis Pond aka Salmon Lake, by boating through the well marked ''Narrows'' thoroughfare where the public boat ramp access is.

Quaint Little Cottage

Clean, quiet, cozy, and includes extras that will make your stay a comfortable one. Located in the Belgrade Lakes region this home is nearby Colby and Thomas College, Maine General and NorthernLight 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 10 minutes, or you can stay in and have delivery from one of our local eateries.

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 .

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.

Sweet Retreat: 2 BDR Home Mins to Colby

Minutes from from Colby College (1.5 miles) , Inland Hospital (1 mile), Maine General (2 miles), Exit 127 on I-95 (5 miles). Forced air heat, WiFi, TV (Hulu & Netflix).The apartment is in a quiet, family friendly Waterville neighborhood on the second story of a two family home- has a private entrance, parking, two bedrooms (queen beds), one bathroom (full bath), dining area, fully equipped kitchen ( stove, oven, microwave), Screened in porch and patio.

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.