Hot Oakland Cottage Rates

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Featured Cottages in Oakland

The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

Oakland
When you stay at this cottage in Oakland, you'll be on a lake, a 1-minute drive from Deep Creek Lake and 9 minutes from Wisp Resort.
Opens in a new windowThe Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek
Bear Hollow Lodge

Bear Hollow Lodge

4 out of 5
20590 GARRETT HWY, Oakland, MD
When you stay at this vacation home in Oakland, you'll be on a lake, a 1-minute drive from Deep Creek Lake and 8 minutes from Wisp Resort.
Opens in a new windowBear Hollow Lodge
Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard

Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard

Oakland
Located in Oakland, this cottage is in a rural location, a 4-minute drive from Deep Creek Lake and 7 minutes from Funland.
Opens in a new windowQuaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard
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Bears Lair

Bears Lair

4 out of 5
94 LEHMAN LN, Oakland, MD
With a stay at this vacation home in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Opens in a new windowBears Lair
Mountain Freedom

Mountain Freedom

4 out of 5
705 MOUNTAINVIEW DR, Oakland, MD
With a stay at this vacation home in Oakland (Mountainside), you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.
Opens in a new windowMountain Freedom
Kare Bear Cabin

Kare Bear Cabin

3.5 out of 5
158 GLENDALE RD, Oakland, MD
With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State Park.
Opens in a new windowKare Bear Cabin
Butterfly Retreat

Butterfly Retreat

4 out of 5
1489 MOUNTAINVIEW DR, Oakland, MD
With a stay at this vacation home in Oakland (Mountainside), you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.
Opens in a new windowButterfly Retreat
A Beautiful View

A Beautiful View

4 out of 5
41 FOX DEN RD, Oakland, MD
With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 9 minutes from Wisp Resort.
Opens in a new windowA Beautiful View
Whispering Pines

Whispering Pines

3.5 out of 5
178 WINDING TRAIL LN # 5B, Oakland, MD
With a stay at this vacation home in Oakland, you'll be a 2-minute drive from Deep Creek Lake and 8 minutes from Deep Creek Lake State Park.
Opens in a new windowWhispering Pines
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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
118 Cottages
Lowest Price
AU$185
Highest Price
AU$185
Popular accommodation
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek, Bear Hollow Lodge, Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard, Bears Lair, Mountain Freedom, Kare Bear Cabin, Butterfly Retreat, A Beautiful View, Whispering Pines

Top trending hotels in Oakland

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy, Oakland, MD
Fully refundableReserve now, pay when you stay
With a stay at Baja Motel in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Mountain Lake Park Town Hall.
Opens in a new windowBaja Motel
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway, Oakland, MD
The price is AU$185 per night from 21 Sept to 22 Sept
AU$185
21 Sept - 22 Sept
includes taxes & fees
When you stay at The Garrett Inn in Oakland, you'll be near the beach, within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Opens in a new windowThe Garrett Inn
Amazing Central Location! Lakefront! Hot tub/dock!

Amazing Central Location! Lakefront! Hot tub/dock!

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront, a 1-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State ...
Opens in a new windowAmazing Central Location! Lakefront! Hot tub/dock!
Save an average of 15% on thousands of hotels when you're signed in
New: Lakefront Luxury Home with Private Indoor Heated Pool!

New: Lakefront Luxury Home with Private Indoor Heated Pool!

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront, a 2-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State ...
Opens in a new windowNew: Lakefront Luxury Home with Private Indoor Heated Pool!
Don't see what you're looking for?
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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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^Subject to availability and chosen travel dates.