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.
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek
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.
Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard
Close to everything DCL, fun for the whole family

Close to everything DCL, fun for the whole family

Oakland
With a stay at this cottage in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 6 minutes from Deep Creek Lake State Park.
Close to everything DCL, fun for the whole family
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Oakland Retreat ~ 13 Mi to Deep Creek Lake!

Oakland Retreat ~ 13 Mi to Deep Creek Lake!

3 out of 5
Oakland
With a stay at this cottage in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Deer Park Town Hall.
Oakland Retreat ~ 13 Mi to Deep Creek Lake!
Lucky 12

Lucky 12

3.5 out of 5
82 Mountainview Court, Oakland, MD
With a stay at this cottage in Oakland (Mountainside), you'll be a 3-minute drive from Deep Creek Lake and 8 minutes from Wisp Resort.
Lucky 12
Deep Breath

Deep Breath

3.5 out of 5
22 Trailside Way, Oakland, MD
With a stay at this cottage in Oakland (Silver Ridge), you'll be a 1-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State Park.
Deep Breath
Private Family Home w/ Deck, Porch + Forest Views!

Private Family Home w/ Deck, Porch + Forest Views!

3 out of 5
Oakland
With a stay at this cottage in Oakland, you'll be within a 10-minute drive of Deep Creek Lake and Deer Park Town Hall.
Private Family Home w/ Deck, Porch + Forest Views!
Schmidt Lodge

Schmidt Lodge

3.5 out of 5
153 Mallard Loop, Oakland, MD
With a stay at this cottage in Oakland, you'll be on a lake, within a 10-minute drive of Deep Creek Lake and Deer Park Town Hall.
Schmidt Lodge
Fox Den

Fox Den

3.5 out of 5
137 Paradise Gardens Road, Oakland, MD
When you stay at this cottage in Oakland, you'll be next to a golf course, a 3-minute drive from Deep Creek Lake and 8 minutes from Deep Creek Lake State ...
Fox Den
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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
14 Cottages
Lowest Price
AU$184
Highest Price
AU$227
Popular accommodation
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek, Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard, Close to everything DCL, fun for the whole family, Oakland Retreat ~ 13 Mi to Deep Creek Lake!, Lucky 12, Deep Breath, Private Family Home w/ Deck, Porch + Forest Views!, Schmidt Lodge, Fox Den

Top trending hotels in Oakland

Riverside Suites

Riverside Suites

2 out of 5
1501 Maryland Hwy, Oakland, MD
Fully refundableReserve now, pay when you stay
The price is AU$227 per night from 9 May to 10 May
AU$227
includes taxes & fees
9 May - 10 May
With a stay at Riverside Suites in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Mountain Lake Park Town Hall.
Riverside Suites
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway, Oakland, MD
The price is AU$184 per night from 27 Apr to 28 Apr
AU$184
includes taxes & fees
27 Apr - 28 Apr
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.
The Garrett Inn
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Oakland
With a stay at this vacation home in Oakland, you'll be a 3-minute drive from Deep Creek Lake and 9 minutes from Wisp Resort.
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp
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In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Oakland
With a stay at this vacation home in Oakland, you'll be a 3-minute drive from Deep Creek Lake and 7 minutes from Wisp Resort.
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
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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.