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Cottages in Oakland

Lakefront Maine House ~ 4 Mi to Colby College
House (4 Bedrooms) | Interior

Lakefront Maine House ~ 4 Mi to Colby College

3.0 star property
Lakefront Maine House ~ 4 Mi to Colby College
Private Dock on Messalonskee Lake: Cozy Cottage!
Cottage (2 Bedrooms) | Interior

Private Dock on Messalonskee Lake: Cozy Cottage!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
Private Dock on Messalonskee Lake: Cozy Cottage!
Near Waterville: Cozy Midcoast Vacation Rental!
House (3 Bedrooms) | Interior

Near Waterville: Cozy Midcoast Vacation Rental!

3.0 star property
Near Waterville: Cozy Midcoast Vacation Rental!
Readfield Retreat w/ Lake Maranacook Views!
House (3 Bedrooms) | Interior

Readfield Retreat w/ Lake Maranacook Views!

3.0 star property
Readfield Retreat w/ Lake Maranacook Views!
Private Dock & Deck: Tranquil Dam Pond Cottage!
Cottage (2 Bedrooms) | Interior

Private Dock & Deck: Tranquil Dam Pond Cottage!

3.0 star property
Private Dock & Deck: Tranquil Dam Pond Cottage!
Quaint Oakland Getaway on East Pond Lake!
Terrace/patio

Quaint Oakland Getaway on East Pond Lake!

2.0 star property
9.0 out of 10, Wonderful, (2)
"Lovely little cabin on a lake. No frills just quiet! Bed very comfortable. Hot water in shower. Dishes and accessories all provided. Only additions could be a coffee maker. French press was there but I was looking for a regular drip pot. Some better assortment of games might be nice too. Playing Clue with only 2 people is a little pointless!! 😂😂😂 Country Deli on the corner was great for coffee and sandwiches. Less than a mile up the road. "
Quaint Oakland Getaway on East Pond Lake!
The Locke-ness Pond Cabin in Chesterville!
House (3 Bedrooms) | Interior

The Locke-ness Pond Cabin in Chesterville!

3.0 star property
The Locke-ness Pond Cabin in Chesterville!
Charming Wilton Vacation Rental w/ Fire Pit
House (4 Bedrooms) | Interior

Charming Wilton Vacation Rental w/ Fire Pit

3.0 star property
Charming Wilton Vacation Rental w/ Fire Pit
Cozy & Peaceful Waterfront Cabin on Porter Lake!
House (3 Bedrooms) | Front of property

Cozy & Peaceful Waterfront Cabin on Porter Lake!

3.0 star property
Cozy & Peaceful Waterfront Cabin on Porter Lake!
Peaceful Lakefront Maine Cabin w/ Sunset Views
House (3 Bedrooms) | Interior

Peaceful Lakefront Maine Cabin w/ Sunset Views

3.0 star property
Peaceful Lakefront Maine Cabin w/ Sunset Views
2 Mi to Colby College: Peaceful Home in Waterville
House (1 Bedroom) | Interior

2 Mi to Colby College: Peaceful Home in Waterville

3.0 star property
2 Mi to Colby College: Peaceful Home in Waterville
Pet-friendly Togus Pond Home: Kayak & Canoe!
Interior

Pet-friendly Togus Pond Home: Kayak & Canoe!

3.0 star property
Pet-friendly Togus Pond Home: Kayak & Canoe!
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
House (2 Bedrooms) | Interior

Unique Maine Log Cabin w/ Trout Ponds & Sauna!

3.0 star property
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
Waterville Home Rental w/ Private Yard + Deck!
House (5 Bedrooms) | Interior

Waterville Home Rental w/ Private Yard + Deck!

3.0 star property
Waterville Home Rental w/ Private Yard + Deck!
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
House (2 Bedrooms) | Interior

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

3.0 star property
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Maine Cottage w/ Dock & Kayaks, Near Augusta!
Cottage (2 Bedrooms) | Interior

Maine Cottage w/ Dock & Kayaks, Near Augusta!

3.0 star property
Maine Cottage w/ Dock & Kayaks, Near Augusta!
Life on the Lake With Private Dock & Fire Pit!
Cottage (2 Bedrooms) | Interior

Life on the Lake With Private Dock & Fire Pit!

3.0 star property
Life on the Lake With Private Dock & Fire Pit!
Cape House in Farmington w/ Shared Outdoor Pool!
Interior

Cape House in Farmington w/ Shared Outdoor Pool!

3.0 star property
Cape House in Farmington w/ Shared Outdoor Pool!
Annabessacook Lake Retreat w/ Deck: Pets Welcome!
House (3 Bedrooms) | Interior

Annabessacook Lake Retreat w/ Deck: Pets Welcome!

3.0 star property
Annabessacook Lake Retreat w/ Deck: Pets Welcome!
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

Comfort Inn & Suites Wilton

Comfort Inn & Suites Wilton

10/10 Excellent
"Clean, friendly, location, and amazing pillows. Not just great pillows, head snugging "wow" fluffy, foam squishy things from heaven. "
Marie 1-night trip
Posted 2 days ago
Comfort Inn & Suites Wilton

Frequently asked questions

How much do cottages in Oakland cost?
You'll pay between and 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 19 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 vacation 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!