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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cottage in Oakland
The Rocky Road Camp on East Pond
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
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5.0 out of 5 average rating, 125 reviews
Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
4.99 out of 5 average rating, 91 reviews, 3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
5.0 out of 5 average rating, 103 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Guest favourite
Home in Oakland
Rustic lakefront cabin on beautiful Belgrade Lakes
4.9 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 1 bathroom
1–6 Sept
Guest favourite
Home in Oakland
Peaceful 5 bedroom 4.5 bath waterfront house
5.0 out of 5 average rating, 36 reviews, 5 bedrooms, 12 beds, 4.5 bathrooms
25–30 Aug
Top guest favourite
Cottage in Oakland
Lakefront camp with kayaks, swimming and views!
4.95 out of 5 average rating, 37 reviews, 4 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
Guest favourite
Home in Oakland
The Lake House on McGrath Pond | 4BR | Waterfront
4.86 out of 5 average rating, 22 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
24–31 Aug
Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4.93 out of 5 average rating, 60 reviews, 4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
Top guest favourite
Room in Oakland
Oakland
4.99 out of 5 average rating, 458 reviews, 1 bed, 1 bathroom
28 Jul – 2 Aug
Cabin in Oakland
Beautiful Cabin on McGrath Pond
3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Guest favourite
Cottage in Oakland
Lakefront cottage in Belgrade Lakes
4.9 out of 5 average rating, 61 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
Guest favourite
Home in Oakland
Updated 4br Family Home Near Belgrade Lakes
4.92 out of 5 average rating, 149 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
4.91 out of 5 average rating, 34 reviews, 2 bedrooms, 5 beds, 1 bathroom
2–9 Aug
Top guest favourite
Home in Oakland
Lake-House on water, East Lake, Near Waterville
4.91 out of 5 average rating, 107 reviews, 5 bedrooms, 8 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Home in Oakland
Quaint Little Cottage
4.97 out of 5 average rating, 88 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–13 Aug
Top guest favourite
Home in Oakland
Lakefront cottage on East Pond
5.0 out of 5 average rating, 19 reviews, 4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct