Photo by Marc Maheu

Search Cottages in Oakland

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Cottages in Oakland and around

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
View from property
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
9.4 out of 10, Exceptional, 109 reviews
"The property had everything we needed and more. Access to lake and nice beach with bathroom. We had a very peaceful visit. Would highly recommend. Great for kids."
The price is €178
includes taxes & fees
23 Jun - 24 Jun
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof
Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof
10.0 out of 10, Exceptional, 107 reviews
"Peter and Jane are terrific hosts of a beautiful spot on the lake. We did all the things. We hiked Mt. Blue to the top. We peddled the boat out onto the lake. We watched the sunrise and sunset on the screened in porch. We made fires and roasted marshmallows. We had a terrifically beautiful family vacation at this perfect little cottage on the lake."
Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof
The Cabbage on Olive Street, overlooking Hayden Brook
Property grounds
The Cabbage on Olive Street, overlooking Hayden Brook
10.0 out of 10, Exceptional, 3 reviews
"Met our needs very well located. We would certainly recommend for future use"
The Cabbage on Olive Street, overlooking Hayden Brook
Three waterfront cottages with private sandy beach - Family Getaway
On the beach
Three waterfront cottages with private sandy beach - Family Getaway
10.0 out of 10, Exceptional, 20 reviews
"WE HAD AN AMAZING STAY! MOST ENJOYABLE AND BEAUTIFUL PROPERTY"
Three waterfront cottages with private sandy beach - Family Getaway
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
Property grounds
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
7.6 out of 10, Good, 22 reviews
"The location of King’s Kastle on Salmon Lake is excellent. The lake is wide at that point and offers great views of the sunrise, particularly from the upstairs master bedroom suite. The lake has less development than others where we have stayed in Maine. We enjoyed seeing loons, eagles, and osprey which are abundant. We went in the latter part of August when the kids’ summer camps had closed, which reduced boat traffic. The cottage is roomy and has a long list of amenities. All appliances were...
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
Cozy Lake House on Cobbosseeconte Lake
Outdoor dining
Cozy Lake House on Cobbosseeconte Lake
10.0 out of 10, Exceptional, 39 reviews
"The almost permanent view of the lake was magnificent. Since the lake is west of the property, the sunsets are also wonderful. I even took one of the kayaks out to the Lighthouse. Even though it looks far away but it only took about 10 minutes of easy paddling. Great place for a peaceful vacation. Bar Harbour was close enough for quick day trip and then the Loop at Acadia Nat'l Park provided great panoramic views."
The price is €625
includes taxes & fees
20 Jun - 21 Jun
Cozy Lake House on Cobbosseeconte Lake
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.6 out of 10, Exceptional, 42 reviews
"The picture you show was the owners 1st property and we could not access the property with my elderly family. When I called the owner, he offered me a second option of another property. That is the property I rated. It was very kind of the owner to accomodate us. It was a lit more driving than we intended but the accommodstions were much better for us."
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Unique Cottage
Exterior
Unique Cottage
10.0 out of 10, Exceptional, 21 reviews
"We would definitely choose to go back to this cottage if we were to vacation in that area again!"
Unique Cottage
Dog-friendy lakefront cottage w/gas fireplace, firepit, dock, grill, & 3 kayaks
Fridge, microwave, oven, stovetop
Dog-friendy lakefront cottage w/gas fireplace, firepit, dock, grill, & 3 kayaks
8.8 out of 10, Excellent, 3 reviews
"This place has a great waterfront perch, with nice swimming off the dock and a full complement of kayaks. House was well-outfitted and super-comfy, with big windows to enjoy the soothing pond view, even on a rainy day. The one downside was cleaning: we were greeted with a bunch of dirty utensils—does anybody look at what’s in the drawer?—a hurriedly wiped fridge and clump of hair in the shower."
Dog-friendy lakefront cottage w/gas fireplace, firepit, dock, grill, & 3 kayaks
Peaceful lakeside getaway
Property grounds
Peaceful lakeside getaway
9.8 out of 10, Exceptional, 66 reviews
"We enjoyed our stay !!! Very convenient and beautiful location"
Peaceful lakeside getaway
Lake Great Pond, Dog Friendly, Boat Ramp & Trailer parking
Terrace/patio
Lake Great Pond, Dog Friendly, Boat Ramp & Trailer parking
10.0 out of 10, Exceptional, 25 reviews
"Everything went well with our stay. Alana was timely and helpful in all our communications. The property was clean and exactly as presented in the listing. My wife is handicapped with mobility issues and found getting around was no problem. The only challenge for us was using the TV, since we are not up on the latest technology. We also aren’t familiar with the immediate area which made it harder for us to find alternatives to our planned outside activities on rainy days."
Lake Great Pond, Dog Friendly, Boat Ramp & Trailer parking
Bright, new cottage w/ open loft, farm view and trails.
Fridge, microwave, oven, stovetop
Bright, new cottage w/ open loft, farm view and trails.
9.8 out of 10, Exceptional, 12 reviews
"Beautiful spot, quiet and private. Home was clean, it had everything we needed for a peaceful getaway."
The price is €187
includes taxes & fees
25 Jun - 26 Jun
Bright, new cottage w/ open loft, farm view and trails.
Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop
Cottage on Cobbosseecontee Lake. Dates available.
10.0 out of 10, Exceptional, 151 reviews
"Had an awesome time staying at Kara’s house on Lake Cobbosseecontee in Winthrop. She was an excellent host and the property is amazing. Absolutely are looking forward to going back next year. Thanks again"
Cottage on Cobbosseecontee Lake. Dates available.
Family Cottage On Androscoggin Lake
Property grounds
Family Cottage On Androscoggin Lake
9.6 out of 10, Exceptional, 29 reviews
"Large beautiful Lake with excellent kayaking and fishing. Cabin well supplied and very clean. Owners very friendly and helpful. Spectacular Sunsets with campfire on Lake."
Family Cottage On Androscoggin Lake
Life on the Lake with Private Dock & Fire Pit!
Beach
Life on the Lake with Private Dock & Fire Pit!
9.8 out of 10, Exceptional, 13 reviews
"The property was gust what we wanted. Peaceful spot and well equipped and comfortable. The only short coming was the the kitchen equipment. We opted to buy some pans to allow proper meal preparation."
Life on the Lake with Private Dock & Fire Pit!
Peaceful lakefront home steps from the water. Private dock!
Property grounds
Peaceful lakefront home steps from the water. Private dock!
Peaceful lakefront home steps from the water. Private dock!
The cottage sits on Belgrade Lake, perfect for relaxing in the heat.
Property grounds
The cottage sits on Belgrade Lake, perfect for relaxing in the heat.
The cottage sits on Belgrade Lake, perfect for relaxing in the heat.
Belgrade lakes waterfront on Messalonskee 4 bedroom cabin
Interior
Belgrade lakes waterfront on Messalonskee 4 bedroom cabin
6.0 out of 10, 2 reviews
"Property was as expected. No frills just a small cabin, clean and has everything one would need. Landscaping and some updates needed but not required. A little more “rustic” than I thought but overall it was a good stay."
Belgrade lakes waterfront on Messalonskee 4 bedroom cabin
Vintage Rustic Cottage on Brettun’s Pond, boat accessible, PET FRIENDLY!
Property grounds
Vintage Rustic Cottage on Brettun’s Pond, boat accessible, PET FRIENDLY!
9.2 out of 10, Wonderful, 57 reviews
"Cabin was well stocked with supplies and just about anything you could need. The cabin could definitely use some upgrades including a way of locking the premises, shower losing warm water consistently, and mice definitely being active. Yard had a lot of dog poop that wasn't cleaned up. Overall enjoyed our stay due to location and privacy of the beautiful lakefront property."
Vintage Rustic Cottage on Brettun’s Pond, boat accessible, PET FRIENDLY!
Don't see what you're looking for?
See all available properties in Oakland
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.

Other property types in Oakland

Central Maine Apartment offering 4 Seasons of Fun.
TV
Central Maine Apartment offering 4 Seasons of Fun.
9.8 out of 10, Exceptional, 25 reviews
"This was such an awesome place To stay. They had snacks and coffee. Enjoyed all the special touches!"
The price is €239
includes taxes & fees
23 Jun - 24 Jun
Central Maine Apartment offering 4 Seasons of Fun.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.6 out of 10, Exceptional, 42 reviews
"The picture you show was the owners 1st property and we could not access the property with my elderly family. When I called the owner, he offered me a second option of another property. That is the property I rated. It was very kind of the owner to accomodate us. It was a lit more driving than we intended but the accommodstions were much better for us."
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Fridge, microwave, oven, stovetop
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
7.8 out of 10, Good, 6 reviews
"Everything we had hoped for. :)"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
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.

Oakland Cottages information

Number of reviews
Accommodation
 Cottages
Lowest Price
Highest Price

Recent Reviews in Oakland
Expedia verified reviews

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

5/5 Excellent
"Nice stay, pet friendly"
A verified traveller stayed at Fireside Inn & Suites Waterville
Posted 2 days ago
Fireside Inn & Suites Waterville