Oakland Cottages

A lake surrounded by trees with autumn leaves.

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Our top choices for Oakland cottages

1. Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!

Strong

Jacob Z.

includes taxes & fees

19 Aug - 20 Aug

2. Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

Belgrade

Steve C.

includes taxes & fees

20 Aug - 21 Aug

3. New spacious-charming one bedroom cottage with loft at Wilson Lake Country Club

Wilton

includes taxes & fees

12 Aug - 13 Aug

4. New spacious-charming one bedroom cottage with loft at Wilson Lake Country Club

Wilton

Ashley F.

includes taxes & fees

19 Aug - 20 Aug

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Top Oakland Hotel Reviews

Senator Inn & Spa

10/10 Excellent

"We liked everything about. We only stayed 1 night but we will definitely be back."

Cozy Long Pond Cottage: community access, private mooring & shared dock.

10/10 Excellent

"Overall larger than expected, otherwise exactly as advertised. Had everything we needed. Host very responsive and kind. Easy short walk to community lake areas. Dog friendly which was fine for us, but definitely evidence of dog (hair etc). Would rent again!"

Charming apartment with waterfront access, modern comforts, and lakeside firepit

10/10 Excellent

"This is such a special property. The apartment was well appointed with everything we could need, with huge windows that let you feel like you’re sleeping in a treehouse. We had coffee with the loons every morning on the dock. It’s at the end of a peninsula and the end of the street, so it feels very private. It was the perfect spot to experience a bit of Maine lake life."

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