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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cottage in Oakland
Lakefront camp with kayaks, swimming and views!
4 bedrooms, 5 beds, 2 private bathrooms
8–13 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
4–9 Oct
5.0 out of 5 average rating, 111 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
Home in Oakland
Lakefront 3 bedroom pet friendly on Messalonski
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 94 reviews
Top guest favourite
Room in Oakland
Oakland
1 bed, 1 bathroom
17–22 Oct
4.99 out of 5 average rating, 472 reviews
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 281 reviews
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Home in Oakland
Lakefront Home w/ an optional add-on Cabin Rental
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Sept
New place to stay
Top guest favourite
Home in Oakland
Quaint Little Cottage
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 90 reviews
Superhost
Flat in Oakland
The heart of the Belgrade lakes
2 bedrooms, 3 beds, 1 bathroom
3–8 Sept
4.85 out of 5 average rating, 68 reviews
Cabin in Oakland
Studio Lakefront Dog Friendly | Patio | Firepit
2 beds, 1 bathroom
7–12 Sept
4.85 out of 5 average rating, 34 reviews
Cabin in Oakland
Cozy Maine Lakeside Camp
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.74 out of 5 average rating, 27 reviews
Top guest favourite
Farm stay in Oakland
Fall Foliage Farmhouse Getaway in Oakland
3 bedrooms, 3 beds, 2.5 bathrooms
6–11 Sept
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
28 Sept – 3 Oct
5.0 out of 5 average rating, 125 reviews
Top guest favourite
Cabin in Oakland
Sister a-frame in Woods (A)
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 145 reviews
Guest favourite
Cabin in Oakland
Sister a-frame in Woods (B)
1 bedroom, 4 beds, 1 bathroom
6–11 Sept
4.84 out of 5 average rating, 49 reviews
Superhost
Cabin in Fairfield
Cabin In The Birches #2
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
4.77 out of 5 average rating, 35 reviews
Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
3 bedrooms, 3 queen beds, 2.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 45 reviews
Superhost
Cottage in Oakland
Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets
2 bedrooms, 5 beds, 1 bathroom
3–10 Sept
4.89 out of 5 average rating, 37 reviews