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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
17–22 Aug
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4.95 out of 5 average rating, 84 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, 93 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 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, 10 reviews
Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 107 reviews
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 276 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
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
Home in Oakland
Peaceful 5 bedroom 4.5 bath waterfront house
5 bedrooms, 12 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 38 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, 25 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
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
Flat in Oakland
The heart of the Belgrade lakes
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.87 out of 5 average rating, 67 reviews
Place to stay in Oakland
The Ell Suite
1 bedroom, 1 king bed, 1 bathroom
15–20 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
Top guest favourite
Home in Smithfield
Stunning Lakefront Retreat set on 9 Private acres
3 bedrooms, 8 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds, 1 bathroom
23–30 Aug
4.92 out of 5 average rating, 36 reviews
Cabin in Oakland
Beautiful Cabin on McGrath Pond
3 bedrooms, 4 beds, 1 bathroom
6–11 Aug
4.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Belgrade
Belgrade Lakes Salmon Waterfront
2 bedrooms, 6 beds, 1 bathroom
9–14 Aug
4.88 out of 5 average rating, 34 reviews