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Search results; Over 1,000 homes in Oakland

Top guest favourite
Home in Oakland
Lake-House on water, East Lake, Near Waterville
5 bedrooms, 8 beds, 1 shared bathroom
23–28 Aug
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4.91 out of 5 average rating, 108 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
4.99 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
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
27 Sept – 2 Oct
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
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
4.98 out of 5 average rating, 275 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
5.0 out of 5 average rating, 107 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
2–7 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
Top guest favourite
Cottage in Oakland
The Rocky Road Camp on East Pond
5.0 out of 5 average rating, 125 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Place to stay in Oakland
The Ell Suite
1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4.93 out of 5 average rating, 61 reviews, 4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
4.92 out of 5 average rating, 36 reviews, 2 bedrooms, 5 beds, 1 bathroom
23–30 Aug
Home in Oakland
Belgrade Lakes Messalonskee 4 bedroom cabin
4.83 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
9–14 Aug
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
4.85 out of 5 average rating, 33 reviews, 2 beds, 1 bathroom
7–12 Sept
Top guest favourite
Cabin in Mercer
Cozy Lakefront Retreat
4.94 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Oct
Guest favourite
Cottage in Oakland
Lakefront cottage in Belgrade Lakes
4.9 out of 5 average rating, 62 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
Superhost
Flat in Winslow
Entire 3 BR apartment in Winslow| 2nd FL | 3 BR
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 1 bathroom
8–13 Aug
Top guest favourite
Cabin in Oakland
Sister a-frame in Woods (A)
4.98 out of 5 average rating, 143 reviews, 1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
Superhost
Cabin in Oakland
Sister a-frame in Woods (B)
4.82 out of 5 average rating, 45 reviews, 1 bedroom, 4 beds, 1 bathroom
12–17 Aug