filters

Search results; Over 1,000 homes in Oakland

Photo 1 of 29
Top guest favourite
Home in Oakland
Classy AF Home, walk across the street to Colby!
3 bedrooms, 3 beds, 1 private bathroom
18–23 Oct
,
4.95 out of 5 average rating, 86 reviews
Photo 1 of 28
Top guest favourite
Cabin in Oakland
Cozy Lakeside Cottage in Oakland, ME
2 bedrooms, 4 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 13 reviews
Photo 1 of 29
Top guest favourite
Apartment in Oakland
Home away from home cozy new Apartment in Oakland
2 bedrooms, 2 beds, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 113 reviews
Photo 1 of 29
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, 101 reviews
Photo 1 of 6
Top guest favourite
Room in Oakland
Oakland
1 bed, 1 bathroom
17–22 Oct
4.99 out of 5 average rating, 475 reviews
Photo 1 of 29
Top guest favourite
Guest suite in Oakland
Cozy Studio Flat, Belgrade Lakes Region
1 bedroom, 1 king bed, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 289 reviews
Photo 1 of 29
Guest favourite
Home in Oakland
Peaceful 5 bedroom 4.5 bath waterfront house
5 bedrooms, 12 beds, 4.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 41 reviews
Photo 1 of 19
Superhost
Flat in Oakland
The heart of the Belgrade lakes
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.85 out of 5 average rating, 74 reviews
Photo 1 of 24
Top guest favourite
Home in Oakland
Quaint Little Cottage
2 bedrooms, 3 beds, 1 bathroom
22–27 Oct
4.97 out of 5 average rating, 97 reviews
Photo 1 of 29
Top guest favourite
Home in Oakland
Lake Front with Amazing Sunset on McGrath Pond
4 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.94 out of 5 average rating, 62 reviews
Photo 1 of 29
Home in Oakland
Lakefront Home w/ an optional add-on Cabin Rental
3 bedrooms, 4 beds, 2.5 bathrooms
11–16 Oct
New place to stay
Photo 1 of 29
Guest favourite
Home in Oakland
3BR Lakefront Home w/ Shared Dock, Deck + Fire Pit
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 7 reviews
Photo 1 of 25
Cabin in Belgrade
Rustic cabin w/ private boat launch - McGrath Pond
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
New place to stay
Photo 1 of 29
Guest favourite
Home in Oakland
Leaf peeper paradise 4br central Maine
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.92 out of 5 average rating, 159 reviews
Photo 1 of 29
Guest favourite
Home in Oakland
The Lake House on McGrath Pond | 4BR | Waterfront
4 bedrooms, 6 beds, 2.5 bathrooms
1–6 Oct
4.88 out of 5 average rating, 25 reviews
Photo 1 of 26
Cabin in Oakland
Cozy Maine Lakeside Camp
2 bedrooms, 4 beds, 1 bathroom
19–24 Oct
4.69 out of 5 average rating, 29 reviews
Photo 1 of 25
Top guest favourite
Home in Oakland
Ultra Spacious and Hosts are Gracious
3 bedrooms, 3 queen beds, 2.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 49 reviews
Photo 1 of 29
Guest favourite
Cottage in Oakland
Camp Carleton on East Pond Lake-dock/firepit/canoe
3 bedrooms, 9 beds, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 10 reviews
Photo 1 of 18
Guest favourite
Flat in Oakland
Sunny & Central
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 7 reviews