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Search results; Over 1,000 homes in Oakland

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Guest favourite
Home in Oakland
Lake-House on water, East Lake, Near Waterville
5 bedrooms, 8 beds, 1 shared bathroom
27 Oct – 1 Nov
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4.89 out of 5 average rating, 114 reviews
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Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
2 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds
25–30 Oct
4.99 out of 5 average rating, 100 reviews
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Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
2 bedrooms, 2 beds
23–28 Oct
5.0 out of 5 average rating, 112 reviews
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Guest favourite
Home in Oakland
Peaceful 5 bedroom 4.5 bath waterfront house
5 bedrooms, 12 beds
17–22 Oct
5.0 out of 5 average rating, 41 reviews
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Home in Oakland
Lakefront Home w/ an optional add-on Cabin Rental
3 bedrooms, 4 beds
11–16 Oct
New place to stay
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Guest favourite
Home in Oakland
Rustic lakefront cabin on beautiful Belgrade Lakes
4 bedrooms, 5 beds
1–6 Oct
4.9 out of 5 average rating, 10 reviews
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Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed
1–6 Oct
4.98 out of 5 average rating, 288 reviews
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Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4 bedrooms, 5 beds
1–6 Oct
4.94 out of 5 average rating, 62 reviews
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Cabin in Belgrade
Rustic cabin w/ private boat launch - McGrath Pond
2 bedrooms, 3 beds
1–6 Oct
New place to stay
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Top guest favourite
Room in Oakland
Oakland
1 bed
24–29 Oct
4.99 out of 5 average rating, 475 reviews
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Top guest favourite
Cottage in Oakland
Lakefront camp with kayaks, swimming and views!
4 bedrooms, 5 beds
12–17 Oct
4.95 out of 5 average rating, 38 reviews
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Cabin in Oakland
Cozy Maine Lakeside Camp
2 bedrooms, 4 beds
19–24 Oct
4.68 out of 5 average rating, 28 reviews
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Guest favourite
Home in Oakland
The Lake House on McGrath Pond | 4BR | Waterfront
4 bedrooms, 6 beds
1–6 Oct
4.88 out of 5 average rating, 25 reviews
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Flat in Oakland
The Granite Suite
1 bedroom, 3 beds
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Oakland
Leaf peeper paradise 4br central Maine
4 bedrooms, 5 beds
1–6 Oct
4.92 out of 5 average rating, 159 reviews
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Guest favourite
Cottage in Oakland
Camp Carleton on East Pond Lake-dock/firepit/canoe
3 bedrooms, 9 beds
1–6 Oct
4.9 out of 5 average rating, 10 reviews
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Top guest favourite
Cottage in Oakland
The Rocky Road Camp on East Pond
1 bedroom, 1 queen bed
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
1–6 Oct
5.0 out of 5 average rating, 7 reviews