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Featured Holiday Homes in Oakland

Waterfront retreat with stunning views, dock access and washer/dryer

Waterfront retreat with stunning views, dock access and washer/dryer

Winthrop
With a stay at this vacation home in Winthrop, you'll be on the waterfront, just steps from Cobbosseecontee Lake and a 5-minute drive from Augusta Country ...
Waterfront retreat with stunning views, dock access and washer/dryer
Lakefront, Stunning Home only 30 min to Sugarloaf!

Lakefront, Stunning Home only 30 min to Sugarloaf!

Strong
The price is AU$635 per night from 2 June to 3 June
AU$635
includes taxes & fees
2 June - 3 June
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!
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
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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
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
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Mount Vernon
With a stay at this vacation home in Mount Vernon, you'll be on the waterfront, and 5.1 mi (8.2 km) from Belgrade Lakes Chain and 6.5 mi (10.4 km) from Maranacook ...
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
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$836 per night from 3 June to 4 June
AU$836
includes taxes & fees
3 June - 4 June
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
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!
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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$382
Highest Price
AU$836
Popular accommodation
Waterfront retreat with stunning views, dock access and washer/dryer, Lakefront, Stunning Home only 30 min to Sugarloaf!, Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME, Every window has a spectacular lake view Low fees, Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly, Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting, Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak, Spacious Country Home w/ Hot Tub, near Colby/Thomas, Private and Calming Waterfront to the Rescue!

Top trending hotels in Oakland

Historic 1840’s Farmhouse Duplex with Modern Comfort – Pets Welcome

Historic 1840’s Farmhouse Duplex with Modern Comfort – Pets Welcome

Oakland
The price is AU$652 per night from 2 June to 3 June
AU$652
includes taxes & fees
2 June - 3 June
Located in Oakland, this farm stay is a 1-minute drive from Belgrade Lakes Chain and 5 minutes from Tree Spirits.
Historic 1840’s Farmhouse Duplex with Modern Comfort – Pets Welcome
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
The price is AU$382 per night from 2 June to 3 June
AU$382
includes taxes & fees
2 June - 3 June
Located in Oakland, this vacation home is a 1-minute drive from Belgrade Lakes Chain and 7 minutes from Tree Spirits.
Sister A-Frame in Woods B
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
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
Located in Oakland, this cottage is within a 15-minute drive of Belgrade Lakes Chain and Belgrade Lakes Golf.
Belgrade 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.

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^Subject to availability and chosen travel dates.