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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
Room in Oakland
Oakland
1 bed, 1 bathroom
17–22 Oct
4.99 out of 5 average rating, 464 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, 276 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, 107 reviews
Top guest favourite
Cottage in Oakland
The Rocky Road Camp on East Pond
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 125 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 93 reviews
Flat in Oakland
Oakland Apt on Messalonskee Lake w/ Dock Access!
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.25 out of 5 average rating, 4 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Aug
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
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 Oakland
The heart of the Belgrade lakes
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.86 out of 5 average rating, 65 reviews
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
2 beds, 1 bathroom
23–28 Aug
4.85 out of 5 average rating, 33 reviews
Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
3 bedrooms, 3 queen beds, 2.5 bathrooms
24–29 Aug
4.98 out of 5 average rating, 42 reviews
Guest favourite
Cottage in Oakland
Lakefront cottage in Belgrade Lakes
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.9 out of 5 average rating, 62 reviews
Cottage in Oakland
Belgrade Lakes McGrath Pond
3 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.87 out of 5 average rating, 15 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
Cabin in Oakland
Cozy Maine Lakeside Camp
2 bedrooms, 4 beds, 1 bathroom
9–14 Sept
4.7 out of 5 average rating, 23 reviews
Guest favourite
Home in Oakland
Updated 4br Family Home Near Belgrade Lakes
4 bedrooms, 5 beds, 2.5 bathrooms
16–21 Aug
4.92 out of 5 average rating, 152 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, 144 reviews