Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Luxurious Lakefront Log Home with Private Dock and fenced in yard

Luxurious Lakefront Log Home with Private Dock and fenced in yard

Augusta ME
With a stay at this vacation home, you'll be centrally located in Augusta, within a 10-minute drive of Old Fort Western and Cushnoc Archeological Site.
Opens in a new windowLuxurious Lakefront Log Home with Private Dock and fenced in yard
Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min

Oakland ME
The price is AU$306 per night from 9 Apr to 10 Apr
AU$306
9 Apr - 10 Apr
includes taxes & fees
Located in Oakland, this vacation home is a 5-minute drive from Belgrade Lakes Chain and 5 minutes from Tree Spirits.
Opens in a new windowDiscover Oakland charm near Colby College 10 min
3 Bedroom year round lakefront home on Three Mile Pond with private dock

3 Bedroom year round lakefront home on Three Mile Pond with private dock

China ME
With a stay at this vacation home in South China, you'll be 7.6 mi (12.2 km) from Natanis Golf Course and 8.6 mi (13.9 km) from Kennebec River.
Opens in a new window3 Bedroom year round lakefront home on Three Mile Pond with private dock
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Modern Cornville Ranch

Modern Cornville Ranch

Cornville ME
When you stay at this vacation home in Skowhegan, you'll be 14 minutes by car from Kennebec River.
Opens in a new windowModern Cornville Ranch
Cozy Long Pond Cottage: community access, private mooring & shared dock.

Cozy Long Pond Cottage: community access, private mooring & shared dock.

Rome ME
Located in Oakland, this vacation home is on a lake, within a 15-minute drive of Lake Minnehonk and Belgrade Lakes Golf.
Opens in a new windowCozy Long Pond Cottage: community access, private mooring & shared dock.
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Manchester ME
Located in Manchester, this vacation home is on the waterfront, within a 15-minute drive of Cobbosseecontee Lake and Augusta Country Club.
Opens in a new windowSpectacular Cobbossee Lakefront with Hot Tub & Dog Friendly
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Spacious Country Home w/ Hot Tub, near Colby/Thomas

Sidney ME
Located in Augusta, this vacation home is in a rural location, within a 15-minute drive of Kennebec River and Maine Veterans Memorial Cemetery.
Opens in a new windowSpacious Country Home w/ Hot Tub, near Colby/Thomas
Peaceful Farmhouse Retreat- Pets welcome

Peaceful Farmhouse Retreat- Pets welcome

Oakland ME
The price is AU$595 per night from 31 Mar to 1 Apr
AU$595
31 Mar - 1 Apr
includes taxes & fees
Located in Oakland, this vacation home is in a rural location, within a 10-minute drive of Tree Spirits and Inland Hospital Diabetes.
Opens in a new windowPeaceful Farmhouse Retreat- Pets welcome
Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.

Waterville ME
With a stay at this vacation home in Waterville, you'll be within a 5-minute drive of Redington Museum and Common Street Arts.
Opens in a new windowCozy House in the heart of Waterville Maine.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oakland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oakland vacation homes are the perfect way for you to wing it.

Holiday houses in Oakland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oakland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oakland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oakland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oakland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oakland Holiday Homes essential information

Accommodation
133 Holiday Homes
Lowest Price
AU$306
Highest Price
AU$595
Popular accommodation
Luxurious Lakefront Log Home with Private Dock and fenced in yard, Discover Oakland charm near Colby College 10 min, 3 Bedroom year round lakefront home on Three Mile Pond with private dock, Modern Cornville Ranch, Cozy Long Pond Cottage: community access, private mooring & shared dock., Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly, Spacious Country Home w/ Hot Tub, near Colby/Thomas, Peaceful Farmhouse Retreat- Pets welcome, Cozy House in the heart of Waterville Maine.

Top trending hotels in Oakland

Weekly discounts avail. Get away from it all on the start of  The Belgrade Lakes

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Oakland ME
Located in Oakland, this cottage is on the waterfront, within a 15-minute drive of Belgrade Lakes Chain and Tree Spirits.
Opens in a new windowWeekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Cozy Long Pond Cottage: community access, private mooring & shared dock.

Cozy Long Pond Cottage: community access, private mooring & shared dock.

Rome ME
Located in Oakland, this vacation home is on a lake, within a 15-minute drive of Lake Minnehonk and Belgrade Lakes Golf.
Opens in a new windowCozy Long Pond Cottage: community access, private mooring & shared dock.
Peaceful Farmhouse Retreat- Pets welcome

Peaceful Farmhouse Retreat- Pets welcome

Oakland ME
The price is AU$595 per night from 31 Mar to 1 Apr
AU$595
31 Mar - 1 Apr
includes taxes & fees
Located in Oakland, this vacation home is in a rural location, within a 10-minute drive of Tree Spirits and Inland Hospital Diabetes.
Opens in a new windowPeaceful Farmhouse Retreat- Pets welcome
Save an average of 15% on thousands of hotels when you're signed in
Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

Oakland ME
The price is AU$397 per night from 31 Mar to 1 Apr
AU$397
31 Mar - 1 Apr
includes taxes & fees
Located in Oakland, this guesthouse is on the waterfront, within a 15-minute drive of Tree Spirits and Inland Hospital Diabetes.
Opens in a new windowLakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore
Don't see what you're looking for?
See all available properties in Oakland
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Picks

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^Subject to availability and chosen travel dates.