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Search results; Over 1,000 homes in Oakland

Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4 bedrooms, 5 beds, 2 private bathrooms
5–10 Sept
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4.93 out of 5 average rating, 61 reviews
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, 10 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 93 reviews
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
2 beds, 1 bathroom
23–28 Aug
4.85 out of 5 average rating, 34 reviews
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, 37 reviews
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 277 reviews
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
Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 107 reviews
Guest favourite
Cabin in Oakland
Sister a-frame in Woods (B)
1 bedroom, 4 beds, 1 bathroom
24–29 Aug
4.83 out of 5 average rating, 47 reviews
Top guest favourite
Home in Oakland
Lake-House on water, East Lake, Near Waterville
5 bedrooms, 8 beds, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 110 reviews
Place to stay in Oakland
The Ell Suite
1 bedroom, 1 king bed, 1 bathroom
15–20 Aug
Cabin in Oakland
2BR lakefront - featured on Maine Cabin Masters
2 bedrooms, 4 beds, 1 bathroom
14–19 Aug
4.27 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Oakland
Sister a-frame in Woods (A)
1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.98 out of 5 average rating, 145 reviews
Top guest favourite
Home in Smithfield
Stunning Lakefront Retreat set on 9 Private acres
3 bedrooms, 8 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Sidney
Brook Ridge Retreat
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.86 out of 5 average rating, 117 reviews
Superhost
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds, 1 bathroom
23–30 Aug
4.89 out of 5 average rating, 37 reviews
Top guest favourite
Home in Oakland
Quaint Little Cottage
2 bedrooms, 3 beds, 1 bathroom
21–26 Aug
4.97 out of 5 average rating, 89 reviews
Guest favourite
Flat in Winslow
Entire 3 BR apartment in Winslow| 2nd FL | 3 BR
3 bedrooms, 3 queen beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 7 reviews