Hot Oakland Cottage Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Cottages in Oakland

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.

Strong
The price is AU$204 per night from 1 Dec to 2 Dec
AU$204
includes taxes & fees
1 Dec - 2 Dec
When you stay at this cottage in Strong, you'll be on a lake and 5 minutes by foot from Porter Lake.
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Cottage on Cobbosseecontee Lake. Dates available.

Cottage on Cobbosseecontee Lake. Dates available.

Winthrop
Located in Winthrop, this cottage is on a lake, a 1-minute drive from Cobbosseecontee Lake and 9 minutes from Augusta Country Club.
Cottage on Cobbosseecontee Lake. Dates available.
Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof

Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof

Wilton
A stay at this cottage places you in the heart of Wilton, a 1-minute drive from Wilson Lake and 7 minutes from Wilson Lake Country Club.
Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof
Save an average of 15% on thousands of hotels when you're signed in
Little Beans Cottage on Great Pond, Belgrade ME

Little Beans Cottage on Great Pond, Belgrade ME

Rome
With a stay at this cottage in Oakland, you'll be next to a golf course, just steps from Belgrade Lakes Chain and a 4-minute drive from Belgrade Lakes Golf.
Little Beans Cottage on Great Pond, Belgrade ME
Camp Quality Time on Wilson Lake 3-bedroom, hot tub

Camp Quality Time on Wilson Lake 3-bedroom, hot tub

Wilton
The price is AU$968 per night from 26 Nov to 27 Nov
AU$968
includes taxes & fees
26 Nov - 27 Nov
With a stay at this cottage in Wilton, you'll be within a 5-minute drive of Wilson Lake and Wilson Lake Country Club.
Camp Quality Time on Wilson Lake 3-bedroom, hot tub
Maine Cottage w/ Dock & Kayaks, Near Augusta!

Maine Cottage w/ Dock & Kayaks, Near Augusta!

Augusta
With a stay at this cottage in Augusta, you'll be within a 15-minute drive of Old Fort Western and Cushnoc Archeological Site.
Maine Cottage w/ Dock & Kayaks, Near Augusta!
2 BR Lakefront Cottage in Belgrade Lakes Region

2 BR Lakefront Cottage in Belgrade Lakes Region

Sidney
Located in Augusta, this cottage is on the waterfront, within a 15-minute drive of Belgrade Lakes Chain and Maine Veterans Memorial Cemetery.
2 BR Lakefront Cottage in Belgrade Lakes Region
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

Rome
Located in Oakland, this cottage is within a 15-minute drive of Belgrade Lakes Chain and Belgrade Lakes Golf.
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
The Cabbage on Olive Street, overlooking Hayden Brook

The Cabbage on Olive Street, overlooking Hayden Brook

Madison
Located in Madison, this cottage is a 4-minute drive from Inland Hospital and 8 minutes from Skowhegan State Fairgrounds.
The Cabbage on Olive Street, overlooking Hayden Brook
Don't see what you're looking for?
See all available properties in Oakland
View all properties
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 Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Oakland will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Oakland definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Oakland, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Oakland Cottages essential information

Accommodation
69 Cottages
Lowest Price
AU$204
Highest Price
AU$968
Popular accommodation
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake., Cottage on Cobbosseecontee Lake. Dates available., Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof, Little Beans Cottage on Great Pond, Belgrade ME, Camp Quality Time on Wilson Lake 3-bedroom, hot tub, Maine Cottage w/ Dock & Kayaks, Near Augusta!, 2 BR Lakefront Cottage in Belgrade Lakes Region, Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College, The Cabbage on Olive Street, overlooking Hayden Brook

Top trending hotels in Oakland

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Oakland
Located in Oakland, this cabin is on the waterfront, a 1-minute drive from Belgrade Lakes Chain and 8 minutes from Tree Spirits.
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
The price is AU$390 per night from 7 Dec to 8 Dec
AU$390
includes taxes & fees
7 Dec - 8 Dec
Located in Oakland, this apartment is in a rural location, a 1-minute drive from Belgrade Lakes Chain and 7 minutes from Tree Spirits.
Central Maine Apartment offering 4 Seasons of Fun.
Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!

Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!

Rome
Located in Oakland, this vacation home is on a lake, within a 15-minute drive of Belgrade Lakes Chain and Belgrade Lakes Golf.
Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!
Save an average of 15% on thousands of hotels when you're signed in
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Rome
When you stay at this vacation home in Oakland, you'll be on the waterfront and steps from Belgrade Lakes Chain.
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Don't see what you're looking for?
See all available properties in Oakland
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.