Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Manchester
Located in Manchester, this vacation home is on the waterfront, within a 15-minute drive of Cobbosseecontee Lake and Augusta Country Club.
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME

Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME

Mount Vernon
Located in Mount Vernon, this vacation home is on the waterfront, within a 10-minute drive of Lake Minnehonk and Echo Lake.
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access

The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access

Augusta
Located in Augusta, this vacation home is on the waterfront, within a 15-minute drive of Old Fort Western and Cushnoc Archeological Site.
The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access
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Charming Wilton Vacation Rental w/ Fire Pit

Charming Wilton Vacation Rental w/ Fire Pit

Wilton
With a stay at this vacation home in Wilton, you'll be within a 5-minute drive of Wilson Lake and Wilson Lake Country Club.
Charming Wilton Vacation Rental w/ Fire Pit
Veedon Fleece on the Lake

Veedon Fleece on the Lake

Manchester
Located in Manchester, this vacation home is a 1-minute drive from Cobbosseecontee Lake and 6 minutes from Augusta Country Club.
Veedon Fleece on the Lake
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Augusta
Located in Augusta, this vacation home is on the waterfront, within a 15-minute drive of Old Fort Western and Cushnoc Archeological Site.
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Readfield
With a stay at this vacation home in Readfield, you'll be near the beach, a 4-minute walk from Maranacook Lake and a 4-minute drive from Town Beach.
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Lakefront, Stunning Home only 30 min to Sugarloaf!

Lakefront, Stunning Home only 30 min to Sugarloaf!

Strong
When you stay at this vacation home in Strong, you'll be on the waterfront and 11 minutes by foot from Porter Lake.
Lakefront, Stunning Home only 30 min to Sugarloaf!
Light-Filled Log Home, 4 Wooded Acres, & Lake Access.  The water is 0.4 mi away.

Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.

Fayette
Located in Fayette, this vacation home is in a rural location, within a 5-minute drive of David Pond and Parker Pond.
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
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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
125 Holiday Homes
Lowest Price
AU$396
Highest Price
AU$567
Popular accommodation
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly, Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME, The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access, Charming Wilton Vacation Rental w/ Fire Pit, Veedon Fleece on the Lake, Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak, Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK, Lakefront, Stunning Home only 30 min to Sugarloaf!, Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.

Top trending hotels in Oakland

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Oakland
Located in Oakland, this cabin is on the waterfront, a 1-minute drive from Belgrade Lakes Chain and 8 minutes from Tree Spirits.
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
The price is AU$396 per night from 18 Nov to 19 Nov
AU$396
includes taxes & fees
18 Nov - 19 Nov
Located in Oakland, this apartment is in a rural location, a 1-minute drive from Belgrade Lakes Chain and 7 minutes from Tree Spirits.
Central Maine Apartment offering 4 Seasons of Fun.
Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!

Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!

Rome
The price is AU$567 per night from 18 Nov to 19 Nov
AU$567
includes taxes & fees
18 Nov - 19 Nov
Located in Oakland, this vacation home is on a lake, within a 15-minute drive of Belgrade Lakes Chain and Belgrade Lakes Golf.
Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!
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Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Rome
When you stay at this vacation home in Oakland, you'll be on the waterfront and steps from Belgrade Lakes Chain.
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
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.

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^Subject to availability and chosen travel dates.