Vacation rentals in Oakland

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. Please note some amenities are seasonal. Check out our other listing!

Clean & Comfortable, 2nd Fl Apt

Waterville is a small town just off the interstate in Central Maine and is approximately an hour from all major cities, the mountains, the coast, and about 2 1/2+-hrs to Acadia. The rental is in a residential neighborhood less than a mile from the interstate, Colby, restaurants, shopping, movies, and parks. There are many recreational opportunities nearby to walk/run, hike, bike, and/or kayak. The apartment has a private entrance, on the second floor (13 stairs up) in an owner occupied duplex.

Off-Grid A-Frame - Peaceful w/ Wood Fired Hot Tub

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 Little Pinecone

Unique, comfortable, clean, and close to all amenities while providing a Maine experience. This brand new tiny log home may only be 400 s/f, but it has it all! Enjoy a full kitchen, comfortable furnishings, covered deck with seating and outdoor games, a fire pit for two, and a fun loft. Spend a quiet, cozy day in or explore the lakes region. 5 minutes to Waterville, Colby & Thomas Colleges, and I-95. 15 minutes to Augusta & Maine General Hospital. *Please read other details before booking*

Large house on Farm

Welcome to My Valhalla Farm, a peaceful, pet-friendly 1840’s farmhouse with 3 bedrooms, 2 full bathrooms and a half bath, a full kitchen, outdoor grill and pool, this unique farm stay offers rustic charm with all the modern comforts. Wake up to the sounds of birds and grazing animals, sip coffee on the deck, and spend your days relaxing by the pool or exploring nearby attractions. Whether you’re traveling as a couple, family, or solo guest, this is a serene home base for your Maine getaway.

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.

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.

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.

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 .

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!

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.