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Search results; Over 1,000 homes in Oakland

Guest favourite
Home in Oakland
Updated 4br Family Home Near Belgrade Lakes
4 bedrooms, 5 beds, 2.5 shared bathrooms
19–24 Jul
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4.92 out of 5 average rating, 149 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
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
4.98 out of 5 average rating, 268 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Aug
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
Cabin in Oakland
Beautiful Cabin on McGrath Pond
3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
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
Top guest favourite
Room in Oakland
Oakland
4.99 out of 5 average rating, 458 reviews, 1 bed, 1 bathroom
28 Jul – 2 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
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
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
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
4.84 out of 5 average rating, 32 reviews, 2 beds, 1 bathroom
23–28 Aug
Flat in Oakland
Oakland Apt on Messalonskee Lake w/ Dock Access!
4.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Jul – 3 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
Cabin in Mercer
Cozy Lakefront Retreat
4.94 out of 5 average rating, 65 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Oct
Top guest favourite
Cottage in Sidney
Waterfront Cottage
4.92 out of 5 average rating, 161 reviews, 1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
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
Cottage in Readfield
Call of the Loon
4.98 out of 5 average rating, 51 reviews, 4 bedrooms, 8 beds, 3 bathrooms
14–19 Aug