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Search results; Over 1,000 homes in Oakland

Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
2 bedrooms, 2 beds, 1 bathroom
23–28 Oct
5.0 out of 5 average rating, 111 reviews
Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
2 bedrooms, 4 beds, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 97 reviews
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 285 reviews
Top guest favourite
Room in Oakland
Oakland
1 bed, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 474 reviews
Cabin in Belgrade
Rustic cabin w/ private boat launch - McGrath Pond
2 bedrooms, 3 beds, 1.5 bathrooms
14–19 Sept
New place to stay
Top guest favourite
Home in Oakland
Quaint Little Cottage
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
4.97 out of 5 average rating, 95 reviews
Top guest favourite
Farm stay in Oakland
Fall Foliage Farmhouse Getaway in Oakland
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Oakland
Sunny & Central
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Oakland
Updated 4br Family Home Near Belgrade Lakes
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 158 reviews
Superhost
Cabin in Oakland
Lakeside Cabin Retreat
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
New place to stay
Guest favourite
Cottage in Belgrade
Belgrade Lakes Salmon Waterfront
2 bedrooms, 6 beds, 1 bathroom
11–16 Sept
4.89 out of 5 average rating, 36 reviews
Guest favourite
Home in Sidney
Lakeside retreat/Belgrade Lakes area
4 bedrooms, 6 beds, 2 bathrooms
12–19 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
3 bedrooms, 3 queen beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 47 reviews
Home in Oakland
Lakefront Home w/ an optional add-on Cabin Rental
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Sept
New place to stay
Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds, 1 bathroom
13–20 Sept
4.9 out of 5 average rating, 39 reviews
Top guest favourite
Home in Oakland
Cute 2-bedroom home in convenient central location
2 bedrooms, 3 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 114 reviews