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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
,
4.91 out of 5 average rating, 106 reviews
Top guest favourite
Room in Oakland
Oakland
1 bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 455 reviews
Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 99 reviews
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
2–7 Jul
4.98 out of 5 average rating, 263 reviews
Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
2 bedrooms, 4 beds, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 7 reviews
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
Farm stay in Oakland
Peaceful retreat in Oakland Maine minutes to lake
3 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Oakland
The heart of the Belgrade lakes
2 bedrooms, 3 beds, 1 bathroom
11–16 Jul
4.85 out of 5 average rating, 62 reviews
Top guest favourite
Cottage in Oakland
Lakefront camp with kayaks, swimming and views!
4 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
4.95 out of 5 average rating, 37 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, 139 reviews
Flat in Oakland
2BR Charming apartment w/ Lakeside Firepit & Dock
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.5 out of 5 average rating, 6 reviews
Guest favourite
Cottage in Oakland
Lakefront home w/Dock & Fire Pit + Pet Friendly
2 bedrooms, 2 beds, 1 bathroom
7–12 Jul
4.89 out of 5 average rating, 36 reviews
Top guest favourite
Home in Oakland
Quaint Little Cottage
2 bedrooms, 3 beds, 1 bathroom
29 Jul – 3 Aug
4.97 out of 5 average rating, 86 reviews
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
1 bedroom, 3 beds, 1 bathroom
6–11 Jul
4.84 out of 5 average rating, 31 reviews
Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds, 1 bathroom
2–9 Aug
4.91 out of 5 average rating, 34 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds, 1 bathroom
17–22 Aug
4.99 out of 5 average rating, 88 reviews
Guest favourite
Home in Oakland
Updated 4br Family Home Near Belgrade Lakes
4 bedrooms, 5 beds, 2.5 bathrooms
31 Jul – 5 Aug
4.92 out of 5 average rating, 149 reviews
Top guest favourite
Cottage in Sidney
Waterfront Cottage
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 158 reviews
Cabin in Oakland
2BR lakefront - featured on Maine Cabin Masters
2 bedrooms, 4 beds, 1 bathroom
27 Jul – 1 Aug
4.36 out of 5 average rating, 14 reviews