
House holiday rentals in Oakland
Find and book unique houses on Airbnb
Top-rated house rentals in Oakland
Guests agree: these houses 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!

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

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!!!

Beautiful lakehouse 2.5 hrs Boston, 40 mins Portland
Beautiful lake living: 2.5 hours from Boston, 40 min. from Portland. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

Cozy 3-bedroom residential home on working farm
Ever wanted to chuck it all and buy a farm? We did in 2010 and now want to share it with you. The "Dell" sits at the entrance to Double Z Land & Livestock, a working farm owned and operated by The Abbruzzese family. Rolling hills, open fields, and grazing farm animals grace this 75-acre farm. If you want a glimpse of country life, seek to switch up your work-from-home routine, or just want to get away, come take up residence on the farm. If it's lambing season, you might even see some babies ;)

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.

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/Apple 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 .

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.

Hallowell Hilltop Home with Hot Tub & Sauna
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, 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.

Dockside Retreat - Spring Sale!
This beautiful, newly renovated home is three bedrooms and two bathrooms, with an open living and dining room waiting to give your family or group of friends the ideal Maine vacation experience! On site parking, a lovely yard, a new sauna on a beautiful deck overlooking the water, nearby fields and steps away from the famous Olson House on one side, you can sit on the deck and overlook the working lobster wharf with fishermen coming and going daily on the other side!

The Barnhouse with hot tub
Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

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 house rentals in Oakland
House rentals with a pool

Cove House with Private Pool, Ocean Views, Family

Coastal Retreat with Pool and Cheerful Vibes

Luxe Liberty: Getaway with Heated Indoor Pool!

House in the woods

Ocean View Retreat with Heated Pool / Hot Tub

The Getaway - A River Paradise

SUGARLOAF, TRAILSIDE, 4-BDRM, & AC

Log Cabin on working horse farm
Weekly house rentals

More Boathouse than Lakehouse

Spacious retreat in central Maine

Belgrade Lake house with Dock!

Cozy & Modern 2BR/2BA with Long Pond access

The Maine Oasis - Pondfront Home with Sunset Views

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

Peaceful Lakefront Getaway W/ Sunset Views & Dock

Coveside on Little Sebago
Private house rentals

Hosmer Pond Lake House

Green Acres

The Belle Air

Mountain Escape | Views • Firepit • Near Sugarloaf

Freeport Retreat

Lakefront on Great Pond, Outdoor Hot Tub

Red Cedar Haven | Lakefront • Dock • Kayaks

Classic Maine Lakehouse * 5 Star Views* Boat Dock
Quick stats about house rentals in Oakland

Total holiday rentals
Explore 20 holiday rentals in Oakland

Nightly prices starting at
Oakland holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 1,430 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Oakland holiday rentals include wifi access

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

4.9 Average rating
Oakland stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Boston Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Laurentides Holiday rentals
- Quebec City Area Holiday rentals
- Mont-Tremblant Holiday rentals
- Laval Holiday rentals
- Québec Holiday rentals
- Lanaudière Holiday rentals
- Rentals with a patio Oakland
- Rentals with outdoor seating Oakland
- Rentals with a kayak Oakland
- Pet-friendly rentals Oakland
- Rentals with a firepit Oakland
- Family-friendly rentals Oakland
- Rentals with lake access Oakland
- Waterfront rentals Oakland
- Rentals with a fireplace Oakland
- Rentals with a washing machine and dryer Oakland
- House rentals Maine
- House rentals United States




