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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
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 270 reviews
Top guest favourite
Room in Oakland
Oakland
1 bed, 1 bathroom
5–10 Aug
4.99 out of 5 average rating, 461 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
Quaint Little Cottage
2 bedrooms, 3 beds, 1 bathroom
8–13 Aug
4.97 out of 5 average rating, 88 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 92 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, 104 reviews
Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 9 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Jul
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, 40 reviews
Guest favourite
Cottage in Oakland
Lakefront cottage in Belgrade Lakes
2 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.9 out of 5 average rating, 62 reviews
Guest favourite
Room in Waterville
Welcome to Anchor house!
1 bed, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 13 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, 150 reviews
Flat in Oakland
2BR Charming apartment w/ Lakeside Firepit & Dock
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.5 out of 5 average rating, 6 reviews
Superhost
Flat in Winslow
Entire 3 BR apartment in Winslow. 2nd FL
3 bedrooms, 3 queen beds, 1 bathroom
27 Jul – 1 Aug
New place to stay
Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
4.93 out of 5 average rating, 61 reviews
Top guest favourite
Tiny home in Belgrade
epicurean feast with zen like surroundings
1 bed, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 84 reviews
Guest favourite
Home in Oakland
Classy AF Home, walk across the street to Colby!
3 bedrooms, 3 beds, 1 bathroom
4–9 Aug
4.95 out of 5 average rating, 82 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