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Compare 139 Vacation Homes in Oakland with updated reviews, rates, and availability.

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

Private and Calming Waterfront to the Rescue!
Private and Calming Waterfront to the Rescue!
9.6 out of 10, Exceptional, (77)

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
10.0 out of 10, Exceptional, (240)

The Modern Maine Retreat
The Modern Maine Retreat
10.0 out of 10, Exceptional, (3)

Brand New Waterfront Lake House (completed July 2021)
Brand New Waterfront Lake House (completed July 2021)
10.0 out of 10, Exceptional, (22)

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
10.0 out of 10, Exceptional, (26)

Cozy House in the heart of Waterville Maine.
Cozy House in the heart of Waterville Maine.
9.6 out of 10, Exceptional, (38)
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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Other property types in Oakland

The Modern Maine Retreat
The Modern Maine Retreat
10.0 out of 10, Exceptional, (3)

Cozy Long Pond Cottage: private mooring & shared dock
Cozy Long Pond Cottage: private mooring & shared dock
9.8 out of 10, Exceptional, (13)

The heart of the Belgrade Lakes
The heart of the Belgrade Lakes
10.0 out of 10, Exceptional, (2)
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.
Recent reviews of Oakland hotels
Recent reviews of Oakland hotels

Maine Evergreen Hotel, Ascend Hotel Collection
5/5 Excellent
"Very professional and friendly staff"
A verified traveler stayed at Maine Evergreen Hotel, Ascend Hotel Collection
Posted 20 hours ago