
Vacation rentals in Oakland
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Top-rated vacation rentals in Oakland
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Oakland vacation rentals
Other great vacation rentals in Oakland
Top guest favourite

Apartment in Waterville
5 out of 5 average rating, 8 reviewsDowntown Waterville Apartment
Guest favourite

Apartment in Waterville
4.83 out of 5 average rating, 6 reviewsDeckBnB
Top guest favourite

Home in Belgrade
5 out of 5 average rating, 5 reviewsSalmon Lake Retreat
Top guest favourite

Home in Oakland
4.92 out of 5 average rating, 52 reviewsLake Front with Amazing Sunset on McGrath Pond
Guest favourite

Cottage in Oakland
4.89 out of 5 average rating, 9 reviewsCamp Carleton on East Pond Lake-dock/firepit/canoe
Guest favourite

Cabin in Oakland
5 out of 5 average rating, 6 reviewsWaterfront Maine log cabin

Home in Oakland
5 out of 5 average rating, 5 reviewsFun 4 bedroom lakeside home
Guest favourite

Cabin in Oakland
4.88 out of 5 average rating, 8 reviewsYour Path to Tranquility
Quick stats about vacation rentals in Oakland
Total rentals
70 properties
Nightly prices starting at
$69 CAD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
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- Waterfront rentals Oakland
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- Saddleback Ski Mountain Maine
- Black Mountain of Maine
- Brunswick Golf Club
- Fox Ridge Golf Club
- Lost Valley Ski Area
- Titcomb Mountain
- Sugarloaf Golf Club
- Belgrade Lakes Golf Club
- Martindale Country Club
- Maine Maritime Museum
- Eaton Mountain Ski Resort
- Coastal Maine Botanical Gardens
- Pemaquid Beach
- Rockland Breakwater Light
- Pinnacle Park
- Hermon Mountain Ski Area
- Narrow Place Beach
- Dragonfly Farm & Winery
- The Camden Snow Bowl
- Pebble Beach
- Farnsworth Art Museum
- Samoset Resort
- Islesboro Town Beach
- Redman Beach