A lake surrounded by trees with autumn leaves.

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Oakland cottages

Cottage (2 Bedrooms) | Interior

1. 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
The price is €279
includes taxes & fees
16 Sept - 17 Sept
Private Dock on Messalonskee Lake: Cozy Cottage!
Property grounds

2. 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, (56 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is €383
includes taxes & fees
20 Sept - 21 Sept
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Exterior

3. 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

4. Dog Friendly, Steps to Lake, Golf, & Theate

Dog Friendly, Steps to Lake, Golf, & Theate
Madison
The price is €447
includes taxes & fees
8 Sept - 9 Sept
Dog Friendly, Steps to Lake, Golf, & Theate
Terrace/patio

5. Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks

Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks
Wayne
10.0 out of 10, Exceptional, (2 reviews)
"This is a beautiful, quiet location, and the cabin is well maintained. The grill worked well, the kitchen had everything we needed, and lots of towels were provided, even swim towels, which we didn't expect. There are three bedrooms with doors, though the last is a single pull out that was fine for our 20 year old daughter. The water at the end of the dock is about 3 feet deep, so it'd be a good spot for small children. With 2 kayaks and a canoe, we explored the coastline and saw loons and...
United States
Julie D.
Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks
Exterior

6. 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, (149 reviews)
"Amazing host. Very nice place and very accommodating!!"
United States
Lilly B.
The price is €164
includes taxes & fees
27 Sept - 28 Sept
Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
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

8/10 Good
"Great to stay with pets, but room is a little outdated."
Alexandre 1-night trip
Posted 6 hours ago
Best Western Plus Waterville Grand Hotel

Find out more about Oakland

Oakland Cottages information

Number of reviews
220
Accommodation
88 Cottages
Lowest Price
€164
Highest Price
€447

Frequently asked questions

How much do cottages in Oakland cost?
You'll pay between €164 and €447 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.