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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
23–28 Aug
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4.91 out of 5 average rating, 108 reviews
Top guest favourite
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
4.99 out of 5 average rating, 92 reviews, 3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
4.92 out of 5 average rating, 36 reviews, 2 bedrooms, 5 beds, 1 bathroom
9–16 Aug
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
Cabin in Oakland
Beautiful Cabin on McGrath Pond
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
4.85 out of 5 average rating, 33 reviews, 2 beds, 1 bathroom
23–28 Aug
Cabin in Belgrade
Ellis Cove Cottages, Cottage One
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
1–8 Aug
Top guest favourite
Cottage in Oakland
The Rocky Road Camp on East Pond
5.0 out of 5 average rating, 125 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
4.98 out of 5 average rating, 271 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Sept
Guest favourite
Home in Oakland
Rustic lakefront cabin on beautiful Belgrade Lakes
4.9 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 1 bathroom
1–6 Sept
Top guest favourite
Cottage in Oakland
Lakefront camp with kayaks, swimming and views!
4.95 out of 5 average rating, 37 reviews, 4 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
Cabin in Oakland
2BR lakefront - featured on Maine Cabin Masters
4.27 out of 5 average rating, 15 reviews, 2 bedrooms, 4 beds, 1 bathroom
14–19 Aug
Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
5.0 out of 5 average rating, 104 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Cabin in Oakland
Waterfront on the Belgrade lakes
2 bedrooms, 4 beds, 1 bathroom
17–22 Aug
Top guest favourite
Farm stay in Oakland
Peaceful retreat in Oakland Maine minutes to lake
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
Home in Oakland
Belgrade Lakes Messalonskee 4 bedroom cabin
4.83 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
9–14 Aug
Cottage in Oakland
Belgrade Lakes McGrath Pond
4.87 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Oakland
Quiet, 6 bedroom lakefront home with sandy beach
5.0 out of 5 average rating, 22 reviews, 6 bedrooms, 10 beds, 3 bathrooms
22–29 Aug