Oakland Travel Guide

Tourist Guide

Swallow Falls
Swallow Falls
Gorgeous fall day! Lots of people, but there was room to walk
Swallow falls cliffs. One of my favorite spots to visit in the winter. This trail is directly across the river from the State park side.
By far one of my favorite waterfalls.. Maryland only has a few and this one tops them all.. short hike

Where to stay in Oakland

Default Image

Blakeslee

Blakeslee might not have many top sights, but Deep Creek Lake and Thousand Acres Lakeside Golf Course are two attractions nearby that you can check out.

Blakeslee
Default Image

Timbers on the Yough

While Timbers on the Yough may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Herrington Manor State Park and Broadford Park.

Timbers on the Yough
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway Oakland MD
The price is NZ$205 per night from 10 Feb to 11 Feb
NZ$205
10 Feb - 11 Feb
includes taxes & fees
Stay at this motel in Oakland. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff and the clean rooms in their reviews. Popular ...
9.6/10 Exceptional! (415 reviews)
Clean, quiet, nice amenities - nice!

Reviewed on 6 Feb 2026

The Garrett Inn
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 MD
Stay at this holiday home in Oakland. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Deep Creek Lake and Wisp Resort are located ...
8/10 Very Good! (69 reviews)
Host was great!! Got back to me right away when I had a question. We all had a great time! Great location!!

Reviewed on 18 Jan 2026

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
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 MD
Stay at this family-friendly holiday home in Oakland. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Deep Creek Lake and Wisp Resort are ...
9.4/10 Exceptional! (16 reviews)
My family and I, including our dog Harley, had a great stay. Terry was an amazing host. We had a weather related issue and she was super responsive and extremely helpful. This was our second stay at this property. It fits our needs and was perfect for a few days of skiing and playing in the snow. ...

Reviewed on 5 Jan 2026

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp
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.
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 MD
Stay at this holiday home in Oakland. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Deep Creek Lake and Wisp Resort are located ...
8/10 Very Good! (69 reviews)
Host was great!! Got back to me right away when I had a question. We all had a great time! Great location!!

Reviewed on 18 Jan 2026

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
The winter is coming !!!

The winter is coming !!!

Oakland MD
Stay at this cabin in Oakland. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Deep Creek Lake and Wisp Resort are located nearby.
9.6/10 Exceptional! (51 reviews)
Bring blankets, pillows and clean towels.

Reviewed on 23 Jan 2026

The winter is coming !!!
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 MD
Stay at this family-friendly holiday home in Oakland. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Deep Creek Lake and Wisp Resort are ...
9.4/10 Exceptional! (16 reviews)
My family and I, including our dog Harley, had a great stay. Terry was an amazing host. We had a weather related issue and she was super responsive and extremely helpful. This was our second stay at this property. It fits our needs and was perfect for a few days of skiing and playing in the snow. ...

Reviewed on 5 Jan 2026

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

Popular places to visit

Cities near Oakland