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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
27 Aug – 1 Sept
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4.91 out of 5 average rating, 107 reviews
Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
2 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds
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
13–18 Sept
5.0 out of 5 average rating, 104 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds
26–31 Jul
Top guest favourite
Cottage in Oakland
The Rocky Road Camp on East Pond
1 bedroom, 1 queen bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 125 reviews
Cabin in Oakland
Beautiful Cabin on McGrath Pond
3 bedrooms, 4 beds
19–24 Jul
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed
11–16 Aug
4.98 out of 5 average rating, 269 reviews
Top guest favourite
Room in Oakland
Oakland
1 bed
5–10 Aug
4.99 out of 5 average rating, 459 reviews
Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds
9–16 Aug
4.91 out of 5 average rating, 35 reviews
Top guest favourite
Cottage in Oakland
Lakefront camp with kayaks, swimming and views!
4 bedrooms, 5 beds
9–14 Sept
4.95 out of 5 average rating, 37 reviews
Cabin in Vassalboro
Maine Lakefront Retreat | Kayaks • Fishing • Views
4 bedrooms, 5 beds
15–20 Sept
New place to stay
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
2 beds
23–28 Aug
4.84 out of 5 average rating, 32 reviews
Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4 bedrooms, 5 beds
5–10 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Cabin in Mercer
Cozy Lakefront Retreat
2 bedrooms, 3 beds
3–8 Oct
4.94 out of 5 average rating, 66 reviews
Guest favourite
Home in Oakland
Rustic lakefront cabin on beautiful Belgrade Lakes
4 bedrooms, 5 beds
1–6 Sept
4.9 out of 5 average rating, 10 reviews
Place to stay in Oakland
The Ell Suite
1 bedroom, 1 king bed
19–24 Jul
Guest favourite
Home in Oakland
The Lake House on McGrath Pond | 4BR | Waterfront
4 bedrooms, 6 beds
24–31 Aug
4.86 out of 5 average rating, 22 reviews
Top guest favourite
Tiny home in Belgrade
epicurean feast with zen like surroundings
1 bed
26–31 Jul
4.99 out of 5 average rating, 83 reviews