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Search results; Over 1,000 homes in Oakland

Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
2 bedrooms, 2 beds, 1 private bathroom
4–9 Oct
,
5.0 out of 5 average rating, 111 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds
25–30 Oct
4.99 out of 5 average rating, 94 reviews
Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
2 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
Home in Oakland
Lakefront Home w/ an optional add-on Cabin Rental
3 bedrooms, 4 beds
9–14 Sept
New place to stay
Top guest favourite
Cottage in Oakland
Lakefront camp with kayaks, swimming and views!
4 bedrooms, 5 beds
8–13 Sept
4.95 out of 5 average rating, 38 reviews
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed
18–23 Sept
4.98 out of 5 average rating, 282 reviews
Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4 bedrooms, 5 beds
5–10 Sept
4.94 out of 5 average rating, 62 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Oakland
Classy AF Home, walk across the street to Colby!
3 bedrooms, 3 beds
7–12 Sept
4.95 out of 5 average rating, 84 reviews
Guest favourite
Home in Oakland
The Lake House on McGrath Pond | 4BR | Waterfront
4 bedrooms, 6 beds
1–8 Sept
4.88 out of 5 average rating, 24 reviews
Guest favourite
Cottage in Oakland
Camp Carleton on East Pond Lake-dock/firepit/canoe
3 bedrooms, 9 beds
15–20 Sept
4.89 out of 5 average rating, 9 reviews
Guest favourite
Home in Oakland
Rustic lakefront cabin on beautiful Belgrade Lakes
4 bedrooms, 5 beds
1–6 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Oakland
Quaint Little Cottage
2 bedrooms, 3 beds
9–14 Sept
4.97 out of 5 average rating, 91 reviews
Cabin in Oakland
Cozy Maine Lakeside Camp
2 bedrooms, 4 beds
20–25 Sept
4.74 out of 5 average rating, 27 reviews
Top guest favourite
Farm stay in Oakland
Fall Foliage Farmhouse Getaway in Oakland
3 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
3 bedrooms, 3 queen beds
7–12 Sept
4.98 out of 5 average rating, 45 reviews
Flat in Oakland
2BR Charming apartment w/ Lakeside Firepit & Dock
2 bedrooms, 3 beds
19–24 Sept
4.63 out of 5 average rating, 8 reviews
Superhost
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds
3–10 Sept
4.89 out of 5 average rating, 38 reviews
Place to stay in Oakland
The Ell Suite
1 bedroom, 1 king bed
1–6 Sept