
Waterfront vacation rentals in Oakland
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Oakland
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Loon Lodge
Located on beautiful Damariscotta Lake, "Loon Lodge" is a rustic cabin from another era. Fall asleep to the sound of crickets and frogs and wake every morning to the call of the lake's many loons. The cabin is 30 minutes from Augusta and 15 minutes from Damariscotta. Hiking enthusiasts will enjoy climbing the Camden Hills-a quick 45 minute drive from the lake. You’ll love my place because of the views, the ambiance, the people, and the location. My place is good for couples and solo adventurers.

Cozy cabin with Hot Tub on Lemon Stream
Relax at this unique, conveniently situated 2 bedroom cabin located on Route 27 between Farmington (15 miles) and Kingfield (7 miles). For winter skiing and summer activities as well, Sugarloaf is just 30 minutes away. The cabin is just off the main road to minimize weather issues. Lemon Stream runs through the property and you can go fishing and explore the 3 acre woodland. Nicely furnished with new appliances, a new hot tub, and all the amenities, this little cabin is the perfect getaway!

Quiet cottage on the bay
Settle in at this mid-coast Maine treasure, where you will find more than you hoped for in a getaway. Located in a private neighborhood and setback on a private road on 2.5 acres. You can take a short stroll down a wooded path to the Belfast bay and watch the sunset or simply enjoy the view from living room. The rocky beach gives you access to a wonderful piece of the Maine coastline. Come make some memories at this unique, pet and family-friendly quiet cottage just 1 mile to downtown Belfast.

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak
Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

Lobstermen's ocean-front cottage
Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Waterfront Sunrise Cove Cottage
Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Not recommended for those with mobility issues. Bathroom is downstairs, bedroom is upstairs. Owners live on property with small dog.

On The River 2 with Lucy the resident cat
On the River 2 is located in the heart of the historic downtown Kingfield on Main street with river views of the Carrabassett river. Miss Lucy Lu (Lucy) is the cat residents who lives in this special apartment. She is the host and will greet you. She loves people. She is an indoor kitty. There is a restaurant next door, the gallery is downstairs, swimming out the back of the building. Sugarloaf mountain close by. Mountains of possibilities to explore in the western area of Maine.

Belfast Ocean Breeze
Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.

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!

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.

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.

SkyView Treehouse | Lakefront • Private Hot Tub
Welcome to your dream treehouse escape — tucked among the pines with stunning lake views, a private hot tub, and direct access to Belgrade Stream. Designed for couples, honeymooners, and small families, SkyView Treehouse offers a luxurious retreat in nature. Enjoy starry nights in the hot tub, cozy evenings by the fireplace, and peaceful mornings on your private deck. Rustic charm meets upscale comfort in this unforgettable lakeside getaway.
Popular amenities for Oakland waterfront rentals
Waterfront apartment rentals

Large Home with Great View next to horse farm

Stunning Royal Richmond 2 Br Apartment Get Away!

Downtown waterfront Belfast with amazing views.

Parisian apartment in downtown Belfast, Maine

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front

Downtown Augusta - 1 Bedroom Loft

Panoramic Water Views on the Sheepscot

Welcome to "West Winds at Pemaquid"
Waterfront house rentals

Gorgeous Studio on the Kennebec

LUX Designer Private Waterfront

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

House in a Mountain Valley Near Hiking & Skiing

Riverside

The Riverfront Retreat - 27 minutes to Sugarloaf!

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Private Lake House, Firepit & Amazing Sunset Views
Waterfront condo rentals

Madison Private Resort / 2 bedrooms 2 bathrooms

Oceanfront, dog-friendly 2BR with harbor view

Oceanfront Multi-level Condo with Prime Amenities

Family Condo 5 min to Sugarloaf

Mabel's Maine Studio on the River

1BR Waterview | Deck | Partial AC

2 Rangeley Lake unit 2 Condo Dock, Kayaks and more

Waterviews + Sunsets + Boothbay/Gardens Aglow
Quick stats about waterfront rentals in Oakland

Total vacation rentals
Explore 40 vacation rentals in Oakland

Nightly prices starting at
Oakland vacation rentals start at R1,713 ZAR per night before taxes and fees

Verified guest reviews
Over 970 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Oakland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oakland rentals

4.8 Average rating
Oakland stays are highly rated by guests—averaging 4.8 out of 5!
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- Pemaquid Beach
- Saddleback Ski Mountain Maine
- Belgrade Lakes Golf Club
- Coastal Maine Botanical Gardens
- Hermon Mountain Ski Area
- Black Mountain of Maine
- Dragonfly Farm & Winery
- Sandy Point Beach
- Fox Ridge Golf Club
- Bear Island Beach
- Maine Maritime Museum
- Sugarloaf Golf Club
- Eaton Mountain Ski Resort
- The Camden Snow Bowl
- Brunswick Golf Club
- Wadsworth Cove Beach
- Spragues Beach
- Farnsworth Art Museum
- Narrow Place Beach
- Rockland Breakwater Light
- Islesboro Town Beach
- Three Island Beach
- Driftwood Beach
- North Point Beach




