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Oakland Vacation Packages

Found in a region where you can find some pretty landscapes, Oakland is a great place to explore Western Maryland.

Packages in Oakland

Book a accommodation and flight package with Expedia and earn some savings. We love to minimize your worries by pairing up your lodging and flight bookings for even more great savings. There is a lot your family can do in Oakland with your extra cash.

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With 400 partner airlines and 321,000 worldwide hotels, our exhaustive database can get you to your ideal vacation spot.

For Oakland, Cumberland, you will have a difficult time finding anything better for your budget than the prices at Expedia.

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Oakland Vacation Packages

From Oakland, Pittsburgh is roughly 80 miles northwest, and Charlottesville is 110 miles southeast.

When you start to crave the sights and sounds of Mother Nature, load up your daypack and head to Smoke Hole Caverns, located 30 miles away from Oakland. Another option is Blackwater Falls State Park, 20 miles away.

Snowboard or ski down the trails of Timberline Four Season Resort or Bryce Ski Resort. The first is 25 miles from Oakland, while the second is 50 miles.

If you head 10 miles to the northeast of Oakland you will get to Deep Creek Lake State Park. A trip here gives you the chance to visit Wisp Resort and Thousand Acres Lakeside Golf Course. If you're keen on experiencing even more of the region, go to McHenry and stop by The Drane House and Funland. They are located just 12 miles out of Oakland.

Around 35 miles to the northwest of Oakland is Morgantown, a regional hub where travelers can find West Virginia University, Creative Arts Center and Beverly Hills Memorial Gardens. West Virginia Botanic Garden and Morgantown Farmers Market are also worth calling on.

One of the best ways to enjoy this region's natural landscapes is to go rock climbing or hiking.

As adventure-loving travelers, we're always after an exciting story to impress our co-workers when we get back home. If you try paragliding when you're in Western Maryland, you'll have plenty to talk about.

Rafting and canoeing are some of the exhilarating watersport activities to keep you on the move.

If you plan to visit on on the 4th of July, you better be ready to party. Every year on this day, the entire nation comes together to celebrate Independence Day.

You shouldn't worry about being late for boarding. Just keep in mind that the closest airport is 35 miles to the northwest.

Accommodation in Oakland

It might be a bit difficult finding accommodation in Oakland itself, as there are currently no vacancies showing up on Expedia's up-to-the-minute database. However, If you're able to commute, you can rest your head at the Inn At Deep Creek, 5 miles away in Deer Park.


Top Hotel Deals

See all 291 Hotels in Oakland
$76
The Garrett Inn

The Garrett Inn

17848 Garrett Highway, Oakland
4.7
of 5, from 44 reviews
3.0 out of 5.0

Situated in Oakland, this motel is within 12 mi (20 km) of Wisp Resort, Thousand Acres Lakeside Golf Course, and Cranesville Swamp Natural Area. Big Run State Park and New Germany State Park are also within 20 mi (32 km).

$125
Inn At Deep Creek

Inn At Deep Creek

19638 Garrett Hwy, Oakland
3.9
of 5, from 111 reviews
3.0 out of 5.0

Located in the heart of Oakland, this hotel is 5.7 mi (9.1 km) from Wisp Resort and within 12 mi (20 km) of Thousand Acres Lakeside Golf Course and Cranesville Swamp Natural Area. Big Run State Park and New Germany State Park are also within 16 mi (25 km).

$82
Oak Mar Motel

Oak Mar Motel

208 N 3rd Street, Oakland
4.3
of 5, from 13 reviews
2.5 out of 5.0

Situated in Oakland, this motel is 11.2 mi (18 km) from Cranesville Swamp Natural Area and 11.9 mi (19.1 km) from Cathedral State Park. Thousand Acres Lakeside Golf Course is 14.6 mi (23.5 km) away.

Beautiful, Charming Lakefront Cabin With Stunning Views And Private Dock

Beautiful, Charming Lakefront Cabin With Stunning Views And Private Dock

1585 Pergin Farm Road, Oakland
4.8
of 5, from 33 reviews
0.0 out of 5.0

Situated on a lake, this cabin is 11.5 mi (18.5 km) from Wisp Resort and within 20 mi (32 km) of Thousand Acres Lakeside Golf Course and Cranesville Swamp Natural Area. Cathedral State Park and Big Run State Park are also within 25 mi (40 km).

Memories Made at the Golden Pond Last a Lifetime

Memories Made at the Golden Pond Last a Lifetime

939 Glendale Rd., Oakland
0.0 out of 5.0

Situated on a lake, this condo is 6.7 mi (10.7 km) from Wisp Resort and 6.9 mi (11.2 km) from Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area and Big Run State Park are also within 16 mi (25 km).

Haley Farm Bed & Breakfast

Haley Farm Bed & Breakfast

16766 Garrett Highway, Oakland
3.0 out of 5.0

Situated in Oakland, this bed & breakfast is 8.5 mi (13.7 km) from Wisp Resort and 10.6 mi (17.1 km) from Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area and Cathedral State Park are also within 20 mi (32 km).

Child-friendly Luxurious Lodge one Block From the Lake

Child-friendly Luxurious Lodge one Block From the Lake

267 Gila Trail, Oakland
4.5
of 5, from 24 reviews
0.0 out of 5.0

Situated in Oakland, this vacation home is 3.8 mi (6.1 km) from Wisp Resort and 10.5 mi (16.8 km) from Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area and Big Run State Park are also within 20 mi (32 km).

Wispy Mountain Hop @ Deep Creek Lake

Wispy Mountain Hop @ Deep Creek Lake

140 Taylor Lane, McHenry
0.0 out of 5.0

Situated in Oakland, this chalet is 3 mi (4.9 km) from Wisp Resort and 11.2 mi (18 km) from Cranesville Swamp Natural Area. Thousand Acres Lakeside Golf Course and Casselman River Bridge State Park are also within 25 mi (40 km).

Top Deals on Flights

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.