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Search results; Over 1,000 homes in Oakland

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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
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5.0 out of 5 average rating, 111 reviews
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Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 95 reviews
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Guest favourite
Home in Oakland
Peaceful 5 bedroom 4.5 bath waterfront house
5 bedrooms, 12 beds, 4.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 38 reviews
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Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Cottage in Oakland
Lakefront camp with kayaks, swimming and views!
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.95 out of 5 average rating, 38 reviews
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Farm stay in Oakland
Fall Foliage Farmhouse Getaway in Oakland
3 bedrooms, 3 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 26 reviews
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Guest favourite
Home in Oakland
Rustic lakefront cabin on beautiful Belgrade Lakes
4 bedrooms, 5 beds, 1 bathroom
1–6 Sept
4.9 out of 5 average rating, 10 reviews
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Superhost
Cabin in Oakland
Lakefront Cottage Retreat
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
New place to stay
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Guest favourite
Home in Oakland
The Lake House on McGrath Pond | 4BR | Waterfront
4 bedrooms, 6 beds, 2.5 bathrooms
1–8 Sept
4.88 out of 5 average rating, 24 reviews
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Home in Oakland
Lakefront Home w/ an optional add-on Cabin Rental
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Sept
New place to stay
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Top guest favourite
Home in Oakland
Quaint Little Cottage
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 93 reviews
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Guest favourite
Home in Oakland
Updated 4br Family Home Near Belgrade Lakes
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 156 reviews
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Room in Oakland
Oakland
1 bed, 1 bathroom
17–22 Oct
4.99 out of 5 average rating, 473 reviews
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Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
3 bedrooms, 3 queen beds, 2.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
4.94 out of 5 average rating, 62 reviews
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Cabin in Oakland
Cozy Maine Lakeside Camp
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.74 out of 5 average rating, 27 reviews
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Home in Oakland
Lakefront Maine House ~ 4 Mi to Colby College
4 bedrooms, 6 beds, 1.5 bathrooms
1–6 Sept
4.43 out of 5 average rating, 23 reviews
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Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 282 reviews