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Search results; Over 1,000 homes in Oakland

Guest favourite
Home in Oakland
Classy AF Home, walk across the street to Colby!
3 bedrooms, 3 beds, 1 private bathroom
16–21 Aug
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4.95 out of 5 average rating, 82 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 92 reviews
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, 9 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
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
Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds, 1 bathroom
9–16 Aug
4.92 out of 5 average rating, 36 reviews
Cabin in Oakland
Beautiful Cabin on McGrath Pond
3 bedrooms, 4 beds, 1 bathroom
23–28 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, 108 reviews
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
2 beds, 1 bathroom
23–28 Aug
4.85 out of 5 average rating, 33 reviews
Top guest favourite
Cottage in Oakland
The Rocky Road Camp on East Pond
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 125 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
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, 104 reviews
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
11–16 Aug
4.98 out of 5 average rating, 272 reviews
Cabin in Oakland
2BR lakefront - featured on Maine Cabin Masters
2 bedrooms, 4 beds, 1 bathroom
14–19 Aug
4.27 out of 5 average rating, 15 reviews
Cabin in Belgrade
Ellis Cove Cottages, Cottage One
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
New place to stay
Place to stay in Oakland
The Ell Suite
1 bedroom, 1 king bed, 1 bathroom
3–8 Aug
Cabin in Oakland
Waterfront on the Belgrade lakes
2 bedrooms, 4 beds, 1 bathroom
17–22 Aug
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, 61 reviews
Top guest favourite
Farm stay in Oakland
Peaceful retreat in Oakland Maine minutes to lake
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 22 reviews