
House vacation rentals in Oakland
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Top-rated house rentals in Oakland
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Sail Loft
Just 1 hour from Acadia National Park, "Mayor's Mansion", home to Ralph Johnson, the first Mayor of Belfast and William V Pratt, Chief of Naval Operations during the Depression. Built in 1812 just as the war of 1812 was beginning, this historic Greek Revival is located in the center of Belfast Maine sited along the waters of Penboscot Bay. 2 min walk to the downtown square. 2 bedrooms and 2.5 baths with full kitchen, washer/dryer, and desk for work. No parties that could cause damage or a mess

LUX Designer Private Waterfront
Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Lakefront: Private Hot Tub, Sauna & Free Massages!
Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!

Lakefront Log Cabin on Pleasant Lake
Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

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.

The Modern Lakehouse
This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Hallowell Hilltop Home and Hot Tub
Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub or infrared sauna, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

Farmington! Walk to town & trails! Family-Friendly
We take great pride in providing a stay that you will remember for years to come. Our moose house is well-stocked with all essential amenities and a few extra surprises! Quaint, convenient neighborhood walking distance to UMF and downtown Farmington. Franklin Memorial Hospital is a short drive. Sugarloaf and Rangeley areas are 45 minutes. WIFI and smart TVs. (No cable.) Washer/Dryer with detergent available. Great place to stay for exploring Maine or a visit with your family and friends.

The Barn
I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton, Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

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 .
Popular amenities for Oakland house rentals
House rentals with a pool

Coastal Retreat with Pool and Cheerful Vibes

Luxe Liberty: Getaway with Heated Indoor Pool!

Stay Together in Style

House in the woods

The Getaway - A River Paradise

Ocean View Retreat with Pool / Hot Tub

Home away from home

3.5k sq ft | Pool, Hot Tub, Sauna & More!
Weekly house rentals

Classy AF Home, walk across the street to Colby!

Cute 2-bedroom home in convenient central location

Spacious retreat in central Maine

The HideAway - Starks

Belgrade Lake house with Dock!

Family's Paradise: 3BR/2BA,Game Room & Lake Access

Lake Front with Amazing Sunset on McGrath Pond

NEW! Long Pond Lake View/Pet-Friendly Getaway, ME
Private house rentals

Manor House on Long Pond with water toys!

The Little Castle

2 Acre Waterfront w/Canoes & Kayaks, Game Room

Antique Barn Apartment at Salt Water Farm

Newly built in 2024, Long Pond lake access

Lakefront on Great Pond | Outdoor Hot Tub | Sauna

Waterside Getaway

Wildewood Haven on beautiful Long Pond
Quick stats about house rentals in Oakland
Total rentals
20 properties
Nightly prices starting at
€ 43 before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Rentals with a fire pit Oakland
- Pet-friendly rentals Oakland
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- Waterfront rentals Oakland
- Family-friendly rentals Oakland
- Rentals with lake access Oakland
- Rentals with a kayak Oakland
- Rentals with a patio Oakland
- House rentals Maine
- House rentals United States
- Pemaquid Beach
- Saddleback Ski Mountain Maine
- Belgrade Lakes Golf Club
- Samoset Resort
- Coastal Maine Botanical Gardens
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Fox Ridge Golf Club
- Sandy Point Beach
- Sugarloaf Golf Club
- Black Mountain of Maine
- Bear Island Beach
- Brunswick Golf Club
- Maine Maritime Museum
- Eaton Mountain Ski Resort
- Farnsworth Art Museum
- Spragues Beach
- Narrow Place Beach
- Three Island Beach
- Driftwood Beach
- Wadsworth Cove Beach
- Islesboro Town Beach
- The Camden Snow Bowl
- North Point Beach