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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cottage in Oakland
The Rocky Road Camp on East Pond
1 bedroom, 1 bed, 1 bathroom
11–16 Sept
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5.0 out of 5 average rating, 125 reviews
Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
2 bedrooms, 4 beds, 1 bathroom
8–13 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, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 90 reviews
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
16–21 Jul
4.98 out of 5 average rating, 263 reviews
Top guest favourite
Home in Oakland
Lake-House on water, East Lake, Near Waterville
5 bedrooms, 8 beds, 1 bathroom
27 Aug – 1 Sept
4.91 out of 5 average rating, 106 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
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, 101 reviews
Top guest favourite
Room in Oakland
Oakland
1 bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 456 reviews
Top guest favourite
Cabin in Oakland
Sister a-frame in Woods (A)
1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.98 out of 5 average rating, 140 reviews
Guest favourite
Home in Oakland
Rustic lakefront cabin on beautiful Belgrade Lakes
4 bedrooms, 5 beds, 1 bathroom
1–6 Sept
4.9 out of 5 average rating, 10 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
Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds, 1 bathroom
2–9 Aug
4.91 out of 5 average rating, 34 reviews
Cabin in Vassalboro
Maine Lakefront Retreat | Kayaks • Fishing • Views
4 bedrooms, 5 beds, 1.5 bathrooms
15–20 Sept
New place to stay
Place to stay in Oakland
The Ell Suite
1 bedroom, 1 king bed, 1 bathroom
12–17 Jul
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, 59 reviews
Guest favourite
Cottage in Oakland
Lakefront home w/Dock & Fire Pit + Pet Friendly
2 bedrooms, 2 beds, 1 bathroom
9–14 Jul
4.89 out of 5 average rating, 36 reviews
Guest favourite
Home in Sidney
Brook Ridge Retreat
2 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
4.87 out of 5 average rating, 112 reviews
Flat in Oakland
Oakland Apt on Messalonskee Lake w/ Dock Access!
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
3 bedrooms, 3 queen beds, 2.5 bathrooms
16–21 Aug
4.97 out of 5 average rating, 39 reviews