Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome
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 & shared dock
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
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
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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!
Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Augusta
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.
Private and Calming Waterfront to the Rescue!
Spacious Country Home w/ Hot Tub, near Colby/Thomas

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

Sidney
The price is AU$504 per night from 27 Dec to 28 Dec
AU$504
includes taxes & fees
27 Dec - 28 Dec
Located in Augusta, this vacation home is in a rural location, within a 15-minute drive of Kennebec River and Maine Veterans Memorial Cemetery.
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH

Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH

New Vineyard
When you stay at this vacation home in New Vineyard, you'll be on a lake and within a 5-minute drive of Porter Lake.
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH
Lake House Wooded Vacation Retreat and Nature Escape

Lake House Wooded Vacation Retreat and Nature Escape

Farmington
Located in Farmington, this vacation home is on the waterfront, within a 15-minute drive of UMF Art Gallery and Richardson Tract.
Lake House Wooded Vacation Retreat and Nature Escape
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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
120 Holiday Homes
Lowest Price
AU$405
Highest Price
AU$504
Popular accommodation
Cozy Long Pond Cottage: private mooring & shared dock, Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly, 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!, Private and Calming Waterfront to the Rescue!, Spacious Country Home w/ Hot Tub, near Colby/Thomas, Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH, Lake House Wooded Vacation Retreat and Nature Escape

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
Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome
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 & shared dock
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
The price is AU$405 per night from 29 Dec to 30 Dec
AU$405
includes taxes & fees
29 Dec - 30 Dec
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.
Save an average of 15% on thousands of hotels when you're signed in
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.