
Waterfront holiday rentals in Oakland
Find and book unique waterfront rentals on Airbnb
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 €87 per night before taxes and fees

Verified guest reviews
Over 920 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Oakland holiday rentals include wifi 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!
Top-rated waterfront rentals in Oakland
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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!
4.96 out of 5 average rating, 234 reviews
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
4.94 out of 5 average rating, 243 reviews
Farm house, River, Island, animals & private Chef.
MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!
4.94 out of 5 average rating, 173 reviews
Lakefront Home w/ Dock | Porter Lake | Sugarloaf
Lakefront paradise on Porter Lake with a private dock, swim float, spacious yard, hammock, deck, patio, grill, fast WiFi, smart TVs, and all the comforts of home. Enjoy direct access to Maine’s ATV and snowmobile trail network right from the property, plus excellent fishing, boating, kayaking, swimming, & ice fishing. Just 20 minutes from Farmington and 35 minutes from Sugarloaf Resort and the Bigelow Mountains. Experience Maine lake living at its finest in every season with stunning lake views
4.92 out of 5 average rating, 180 reviews
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
4.99 out of 5 average rating, 99 reviews
Lakeside retreat on quiet cove on Cobbessee Lake!
Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.
4.84 out of 5 average rating, 115 reviews
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.
4.86 out of 5 average rating, 118 reviews
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!
4.92 out of 5 average rating, 173 reviews
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.
4.89 out of 5 average rating, 114 reviews
Timeless Tides Cottage
This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.
4.96 out of 5 average rating, 215 reviews
Visit Beautiful Home on Snow Pond
Belgrade Lakes, Maine's premiere lakes region. Beautiful, four season home on 9 mile long, Messalonskee Lake also known as, Snow Pond. Come to experience life the way it should be. Sunrise view, from master bedroom and lakeside deck surrounded by undeveloped wooded shoreline. Swim, canoe and kayak from private dock. Loons, eagles, osprey, and beavers can be your neighbors for a relaxing week at the lake. Open concept kitchen dinning and living room.
4.82 out of 5 average rating, 128 reviews
Price's Point - Cabin on the water
Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.
5.0 out of 5 average rating, 129 reviewsPopular amenities for waterfront rentals in Oakland
Waterfront apartment rentals

On The River 2 with Lucy the resident cat
4.96 out of 5 average rating, 430 reviews
Stunning Royal Richmond 2 Br Apartment Get Away!
4.92 out of 5 average rating, 186 reviews
"Ship Shape": waterfront, cozy studio- downtown
4.85 out of 5 average rating, 618 reviews
Two bedroom duplex across st from crystal lake
4.95 out of 5 average rating, 184 reviews
Cottrill House on Damariscotta River # 1
4.95 out of 5 average rating, 403 reviews
Garden view near Bowdoin College
4.96 out of 5 average rating, 217 reviews
Loft - Downtown Augusta - 1 Bedroom
4.93 out of 5 average rating, 82 reviews
More Boathouse than Lakehouse
5.0 out of 5 average rating, 27 reviewsWaterfront house rentals

Mirror Pond Cottage
4.92 out of 5 average rating, 149 reviews
Peaceful Oasis by the Great Salt Bay - 3BR/2Ba
4.98 out of 5 average rating, 213 reviews
Modern Lakefront Home w/ Hot Tub • Summer Vacation
4.87 out of 5 average rating, 122 reviews
The Modern Lakehouse
5.0 out of 5 average rating, 246 reviews
The Pearl of Lake Saint George
4.94 out of 5 average rating, 179 reviews
Maine Waterfront Hideaway
4.96 out of 5 average rating, 133 reviews
Extreme Oceanfront House
4.95 out of 5 average rating, 101 reviews
Veedon Fleece on the Lake
4.95 out of 5 average rating, 105 reviewsWaterfront apartment rentals

Waterviews|Sunsets|Boothbay|Gardens Aglow
4.97 out of 5 average rating, 70 reviews
Coastal Sunrise Condo 2 bd (1 king,1 twin) Balcony
4.86 out of 5 average rating, 29 reviews
Oceanfront Multi-level Condo with Prime Amenities
5.0 out of 5 average rating, 9 reviews
Lovely 2 bedroom updated riverside condo with pool
4.96 out of 5 average rating, 69 reviews
Rockland Central Over Main, downtown living
4.7 out of 5 average rating, 10 reviews
Wilson Lake Inn - Studio 1st Floor

Historic Condo in Downtown Camden, steps to Harbor
5.0 out of 5 average rating, 3 reviews
Mabel's Maine Studio on the River
4.4 out of 5 average rating, 5 reviewsWhen is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €268 | €261 | €257 | €230 | €218 | €254 | €268 | €261 | €257 | €238 | €247 | €258 |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Destinations to explore
- Montreal Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Salem Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Bar Harbor Holiday rentals
- Cambridge Holiday rentals
- New Haven Holiday rentals
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Saddleback Ski Mountain Maine
- The Camden Snow Bowl
- Maine Maritime Museum
- Rockland Breakwater Light
- Camden Hills State Park
- Farnsworth Art Museum
- Maine Lighthouse Museum
- Moose Point State Park
- Cellardoor Winery
- Hollywood Slots Hotel & Raceway
- Black Mountain of Maine
- Belgrade Lakes Golf Club
- Range Ponds State Park
- Lost Valley Ski Area
- Sugarloaf Golf Club





