Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

The Johnson House - Historic 5-bedroom Greek Revival in charming Wayne Village!

The Johnson House - Historic 5-bedroom Greek Revival in charming Wayne Village!

Wayne ME
A stay at this vacation home places you in the heart of Wayne, a 1-minute drive from Androscoggin Lake and 8 minutes from Wilson Pond.
Opens in a new windowThe Johnson House - Historic 5-bedroom Greek Revival in charming Wayne Village!
Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min

Oakland ME
The price is AU$293 per night from 25 May to 26 May
AU$293
25 May - 26 May
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
Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Augusta ME
Located in Augusta, this vacation home is on the waterfront, within a 15-minute drive of VA Maine Healthcare System - Togus and Old Fort Western.
Opens in a new windowPrivate and Calming Waterfront to the Rescue!
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Classy AF Home Steps from Colby and Trails

Classy AF Home Steps from Colby and Trails

Oakland ME
With a stay at this vacation home in Oakland, you'll be a 2-minute walk from Colby College and 11 minutes by foot from Gordon Center For Creative & Performing ...
Opens in a new windowClassy AF Home Steps from Colby and Trails
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
Stretch and Space Out on 40 Acres

Stretch and Space Out on 40 Acres

Leeds ME
Located in Leeds, this vacation home is within a 15-minute drive of Androscoggin Lake and Theatre at Monmouth.
Opens in a new windowStretch and Space Out on 40 Acres
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.
The Barn House - Spacious 4-bedroom, 3-bath house in the heart of Wayne Village.

The Barn House - Spacious 4-bedroom, 3-bath house in the heart of Wayne Village.

Wayne ME
Located in Wayne, this vacation home is a 1-minute drive from Androscoggin Lake and 8 minutes from Maranacook Lake.
Opens in a new windowThe Barn House - Spacious 4-bedroom, 3-bath house in the heart of Wayne Village.
Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester ME
The price is AU$469 per night from 17 May to 18 May
AU$469
17 May - 18 May
includes taxes & fees
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 windowCozy Cottage on water's edge of Lake Cobbosseecontee
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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
139 Holiday Homes
Lowest Price
AU$293
Highest Price
AU$507
Popular accommodation
The Johnson House - Historic 5-bedroom Greek Revival in charming Wayne Village!, Discover Oakland charm near Colby College 10 min, Private and Calming Waterfront to the Rescue!, Classy AF Home Steps from Colby and Trails, 3 Bedroom year round lakefront home on Three Mile Pond with private dock, Stretch and Space Out on 40 Acres, Cozy House in the heart of Waterville Maine., The Barn House - Spacious 4-bedroom, 3-bath house in the heart of Wayne Village., Cozy Cottage on water's edge of Lake Cobbosseecontee

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 Belgrade Lakes Chain and Lake Minnehonk.
Opens in a new windowCozy Long Pond Cottage: community access, private mooring & shared dock.
Pool, fire pit & minutes to Messalonskee Lake!

Pool, fire pit & minutes to Messalonskee Lake!

Oakland ME
The price is AU$507 per night from 17 May to 18 May
AU$507
17 May - 18 May
includes taxes & fees
Located in Oakland, this vacation home is in a rural location, a 1-minute drive from Belgrade Lakes Chain and 5 minutes from Tree Spirits.
Opens in a new windowPool, fire pit & minutes to Messalonskee Lake!
Save an average of 15% on thousands of hotels when you're signed in
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

Rome ME
Located in Oakland, this cottage is within a 15-minute drive of Belgrade Lakes Chain and Lake Minnehonk.
Opens in a new windowBelgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Don't see what you're looking for?
See all available properties in Oakland
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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.

Top Picks

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^Subject to availability and chosen travel dates.