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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
11–16 Sept
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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
8–13 Sept
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
4.99 out of 5 average rating, 90 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
Room in Oakland
Oakland
4.99 out of 5 average rating, 456 reviews, 1 bed, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
5.0 out of 5 average rating, 101 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
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
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
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
Lake-House on water, East Lake, Near Waterville
4.91 out of 5 average rating, 106 reviews, 5 bedrooms, 8 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
4.97 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
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
Top guest favourite
Home in Oakland
Quaint Little Cottage
4.97 out of 5 average rating, 86 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–13 Aug
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
4.98 out of 5 average rating, 263 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Jul
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
31 Jul – 5 Aug
Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4.93 out of 5 average rating, 59 reviews, 4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
Top guest favourite
Farm stay in Oakland
Peaceful retreat in Oakland Maine minutes to lake
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
4.84 out of 5 average rating, 32 reviews, 1 bedroom, 3 beds, 1 bathroom
13–18 Jul