Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Belgrade Lake house with Dock!

Belgrade Lake house with Dock!

Rome
Located in Oakland, this vacation home is on a lake, a 1-minute drive from Belgrade Lakes Chain and 9 minutes from Belgrade Lakes Golf.
Belgrade Lake house with Dock!
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
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.
3 Bedroom year round lakefront home on Three Mile Pond with private dock
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
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Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester
The price is AU$492 per night from 17 Aug to 18 Aug
AU$492
17 Aug - 18 Aug
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.
Cozy Cottage on water's edge of Lake Cobbosseecontee
Every window has a spectacular lake view
Low fees

Every window has a spectacular lake view Low fees

Wayne
With a stay at this vacation home in Wayne, you'll be on the waterfront, just steps from Wilson Pond and a 3-minute drive from Mt Pisgah Conservation Area ...
Every window has a spectacular lake view Low fees
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Albion
Located in Albion, this vacation home is on the waterfront, within a 15-minute drive of Lovejoy Pond and Sandy Pond.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
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
Spacious Country Home w/ Hot Tub, near Colby/Thomas

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

Sidney
The price is AU$719 per night from 6 Sept to 7 Sept
AU$719
6 Sept - 7 Sept
includes taxes & fees
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
Lovely Home on Androscoggin Lake

Lovely Home on Androscoggin Lake

Wayne
Located in Wayne, this cottage is on the waterfront, a 1-minute drive from Androscoggin Lake and 9 minutes from Wilson Pond.
Lovely Home on Androscoggin Lake
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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
155 Holiday Homes
Lowest Price
AU$492
Highest Price
AU$719
Popular accommodation
Belgrade Lake house with Dock!, 3 Bedroom year round lakefront home on Three Mile Pond with private dock, Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly, Cozy Cottage on water's edge of Lake Cobbosseecontee, Every window has a spectacular lake view Low fees, Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion , Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak, Spacious Country Home w/ Hot Tub, near Colby/Thomas, Lovely Home on Androscoggin Lake

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
Located in Oakland, this cottage is on the waterfront, within a 15-minute drive of Belgrade Lakes Chain and Tree Spirits.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
32 Belgrade Rd, Oakland, ME
With a stay at Pressey House Lakeside Bed & Breakfast in Oakland, you'll be on the waterfront, just steps from Belgrade Lakes Chain and a 2-minute drive from ...
Pressey House Lakeside Bed & Breakfast
Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

Oakland
Located in Oakland, this cabin is on the waterfront, a 1-minute drive from Belgrade Lakes Chain and 5 minutes from Tree Spirits.
Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!
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Classic and adorable Maine camp on North Pond in the Belgrade Lakes

Classic and adorable Maine camp on North Pond in the Belgrade Lakes

Rome
When you stay at this cabin in Oakland, you'll be on a lake and 11 minutes by car from Belgrade Lakes Chain.
Classic and adorable Maine camp on North Pond in the Belgrade Lakes
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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.