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Search results; Over 1,000 homes in Oakland

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Top guest favourite
Cabin in Oakland
Sister a-frame in Woods (A)
1 bedroom, 3 beds, 1 private bathroom
27 Sept – 2 Oct
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4.98 out of 5 average rating, 148 reviews
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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, 112 reviews
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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, 12 reviews
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Top guest favourite
Room in Oakland
Oakland
1 bed, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 475 reviews
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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, 286 reviews
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Cabin in Belgrade
Rustic cabin w/ private boat launch - McGrath Pond
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Sept
New place to stay
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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, 98 reviews
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Superhost
Flat in Oakland
The heart of the Belgrade lakes
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.85 out of 5 average rating, 71 reviews
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Guest favourite
Cabin in Oakland
Sister a-frame in Woods (B)
1 bedroom, 4 beds, 1 bathroom
6–11 Dec
4.84 out of 5 average rating, 51 reviews
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Guest favourite
Flat in Oakland
Sunny & Central
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds, 1 bathroom
17–24 Sept
4.9 out of 5 average rating, 39 reviews
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Guest favourite
Home in Oakland
Leaf peeper paradise 4br central Maine
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 159 reviews
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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
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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, 96 reviews
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Top guest favourite
Cottage in Oakland
The Rocky Road Camp on East Pond
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 125 reviews
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Guest favourite
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 7 reviews
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Superhost
Cabin in Oakland
Lakeside Cabin Retreat
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
New place to stay
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Home in Oakland
Lakefront Home w/ an optional add-on Cabin Rental
3 bedrooms, 4 beds, 2.5 bathrooms
11–16 Oct
New place to stay
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Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
3 bedrooms, 3 queen beds, 2.5 bathrooms
17–22 Sept
4.98 out of 5 average rating, 48 reviews