A lake surrounded by trees with autumn leaves.

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Oakland cottages

Cottage (2 Bedrooms) | Interior

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
Private Dock on Messalonskee Lake: Cozy Cottage!
Exterior

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
Sidney
9.0 out of 10, Wonderful, (12 reviews)
"Great place to stay for our annual fishing weekend in the Belgrade Lakes region! "
United States
Shawn H.
Private Dock on Messalonskee Lake: Cozy Cottage!
Exterior

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

Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
Strong
9.4 out of 10, Exceptional, (144 reviews)
"Nice little cottage at a good price, thank you! "
United States
Jacob Z.
The price is €152
includes taxes & fees
29 Jul - 30 Jul
Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
Property grounds

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

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (55 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is €547
includes taxes & fees
14 Aug - 15 Aug
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Outdoor dining

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

New spacious-charming one bedroom cottage with loft at Wilson Lake Country Club
Wilton
The price is €239
includes taxes & fees
4 Aug - 5 Aug
New spacious-charming one bedroom cottage with loft at Wilson Lake Country Club
Outdoor dining

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

New spacious-charming one bedroom cottage with loft at Wilson Lake Country Club
Wilton
6.0 out of 10, (2 reviews)
"Tom’s cottage was beautiful and the atmosphere was exactly what we were looking for for our quiet night away! Highly recommend and will definitely be back again soon! "
United States
Ashley F.
The price is €239
includes taxes & fees
26 Jul - 27 Jul
New spacious-charming one bedroom cottage with loft at Wilson Lake Country Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakland Hotel Reviews

Best Western Plus Waterville Grand Hotel

Best Western Plus Waterville Grand Hotel

10/10 Excellent
"Clean property, decent gym, friendly staff"
Shawn 1-night trip
Posted 6 hours ago
Best Western Plus Waterville Grand Hotel

Find out more about Oakland

Oakland Cottages information

Number of reviews
159
Accommodation
88 Cottages
Lowest Price
€152
Highest Price
€547

Frequently asked questions

How much do cottages in Oakland cost?
You'll pay between €152 and €547 per night for cottages in Oakland. No matter your budget, a wonderful stay is only a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Oakland?
Reconnect with nature in one of the 88 cottages located in Oakland. To help you select an ideal property, use our filters to search for perks or amenities you need.
Why book your cottage in Oakland with Expedia?
Booking a cottage in Oakland is as easy as deciding on your travel dates and picking an ideal place for a holiday in nature. From ritzy retreats to low-cost stays and cottages that include perks like a pool, Expedia has something for all tastes. As for the best offers around? We've got them as well!
How can I find cheap cottages in Oakland?
Expedia can help you locate cheap cottages in Oakland. To book your special stay in a couple of clicks, simply use our handy filter tool to refine your search by amenities, star rating and budget.