Vacation rentals in Oakland

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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.

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.

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 paddle board, kayak or keep your own smaller boat at your own dock in this protected shallow cove. Explore the 7 miles of shoreline or check out Ellis aka Salmon Lake, by boating through the well marked ''Narrows'' thoroughfare where the public boat ramp access.

Tiny home on wheels

Experience the charm of camping right in the front yard with this one-of-a-kind tiny home on wheels! Recently built, it features high ceilings, a full-size kitchen, a spacious shower, washer and dryer, a king-size bed, a full-size pullout sofa, and a dining table giving you the comfort and feel of a much larger home. Stay cool with summer AC or unwind by the outdoor fireplace for a cozy evening. Spend your days exploring endless recreational activities, China Lake is just 3 minutes away.

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 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.

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 .

Lakefront camp with kayaks, swimming and views!

Relax with the whole family at this comfortable cottage with amazing views from throughout the house. Gather on the deck or enclosed porch with friends and family, while listening to the loons. Recently renovated while maintaining the traditional Maine "camp" vibe, the 4 bedroom*, 2-bathroom vacation rental has all you need for a comfortable stay. There are cozy reading nooks, places to play games or do puzzles, and dine together.