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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
,
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
31 Aug – 5 Sept
5.0 out of 5 average rating, 8 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
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, 99 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds, 1 bathroom
17–22 Aug
4.99 out of 5 average rating, 88 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, 139 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
Top guest favourite
Home in Oakland
Lake-House on water, East Lake, Near Waterville
5 bedrooms, 8 beds, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 106 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
Place to stay in Oakland
The Ell Suite
1 bedroom, 1 king bed, 1 bathroom
5–10 Jul
Cabin in Vassalboro
Maine Lakefront Retreat | Kayaks • Fishing • Views
4 bedrooms, 5 beds, 1.5 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Farm stay in Oakland
Peaceful retreat in Oakland Maine minutes to lake
3 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Room in Oakland
Oakland
1 bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 455 reviews
Home in Sidney
Log Cabin on the Lake with private dock!
4 bedrooms, 6 beds, 1 bathroom
6–11 Jul
New place to stay
Guest favourite
Cabin in Oakland
Your Path to Tranquility
2 bedrooms, 4 beds, 1.5 bathrooms
26 Jun – 3 Jul
4.92 out of 5 average rating, 12 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 Sidney
Waterfront Cottage
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 158 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
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