
Waterfront holiday rentals in Oakland
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Oakland
Guests agree: These waterfront accommodation options 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.

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!

Modern Lakefront Home w/ Hot Tub • Winter Escape
Grace's Cottage is a charming 1860's cottage on Lake Saint George. Newly remodeled, the 3 bedroom, 1 bath cottage offers a perfect blend of old-world charm and modern amenities. A spacious screened porch overlooks the lake, and a year-round hot tub provides a perfect spot to relax & unwind. This living space is perfect for gathering with family & friends. Whether you're seeking a romantic getaway or a fun-filled family vacation, Grace's Cottage is the perfect home base for your Maine adventure.

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.

Rustic Family Cabin on China Lake
This rustic cabin has been in my family for 4 generations. It's well loved, a bit quirky, sometimes musty and perfect for a family get away. We welcome well trained dogs, and have high expectations that you will respect the place and leave it in good shape for us and future guests. We welcome families, but after bad experiences, we are not available for your group of friends, reunion, or bachelor/(ette) party. We ask you to bring your own linens. The water in the cabin is not drinkable

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.

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.

Cozy log cabin on private pond, near Reid St Park!
Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

Private Lake House, Firepit & Amazing Sunset Views
Escape to Lakeshore Point, a winter wonder in Maine! This updated, modern lakehouse is nestled in the woods overlooking beautiful Canton Lake. Relax, unwind and recharge as you wake up surrounded by nature and incredible water views. With 200' of lakefront, you're just steps away from the lake with your own private sandy beach. Lakeshore Point is the last house on a private dirt road with all the amenities you're looking for- Full kitchen, wifi, outdoor shower and fire pit.

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.
Popular amenities for Oakland waterfront rentals
Waterfront apartment accommodation

Large Home with Great View next to horse farm

Stunning Royal Richmond 2 Br Apartment Get Away!

Downtown waterfront Belfast with amazing views.

Sail Loft - Upscale Oceanfront on a Pier near BBH!

Parisian apartment in downtown Belfast, Maine

Cottrill House on Damariscotta River # 1

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front

Panoramic Water Views on the Sheepscot
Waterfront house rentals

Manor House on Long Pond with water toys!

Waterfront Gem walkable to Restaurants!

Salmon Lake Retreat

LUX Designer Private Waterfront Hot Tub - Secluded

House in a Mountain Valley Near Hiking & Skiing

Riverside

The Riverfront Retreat - 27 minutes to Sugarloaf!

[Trending Now]Belfast City Park Ocean House
Waterfront condo accommodation

Madison Private Resort / 2 bedrooms 2 bathrooms

Oceanfront, dog-friendly 2BR with harbor view

Saddleback | 15 Clubhouse | Ski in/out, Pet friend

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

Waterfront|Sunsets|Boothbay Harbor
Quick stats about waterfront rentals in Oakland

Total holiday rentals
Explore 40 holiday rentals in Oakland

Nightly prices starting at
Oakland holiday rentals start at $141 AUD per night before taxes and fees

Verified guest reviews
Over 1,020 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Oakland holiday 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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