Book Exclusive Oakland Vacation Packages

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Oakland flight + hotel packages

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Holiday Inn Express and Suites Fairmont by IHG

Holiday Inn Express and Suites Fairmont by IHG

2.5 out of 5
Price was CA $2,383, price is now CA $2,285 per person
CA $2,285
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Morgantown (MGW)
Book a stay at this business-friendly hotel in Fairmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Valley Worlds of Fun and Middletown Mall are located nearby.
Holiday Inn Express & Suites Bridgeport by IHG

Holiday Inn Express & Suites Bridgeport by IHG

2.5 out of 5
Price was CA $2,561, price is now CA $2,439 per person
CA $2,439
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Morgantown (MGW)
Book a stay at this business-friendly hotel in Bridgeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cinemark Meadowbrook Mall and Meadowbrook Mall are located nearby.
Courtyard by Marriott Bridgeport Clarksburg

Courtyard by Marriott Bridgeport Clarksburg

3 out of 5
Price was CA $2,473, price is now CA $2,441 per person
CA $2,441
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Morgantown (MGW)
Book a stay at this business-friendly hotel in Bridgeport. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Cinemark Meadowbrook Mall and Meadowbrook Mall are located nearby.
SpringHill Suites Bridgeport Clarksburg

SpringHill Suites Bridgeport Clarksburg

2.5 out of 5
Price was CA $2,471, price is now CA $2,440 per person
CA $2,440
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Morgantown (MGW)
Book a stay at this business-friendly hotel in Bridgeport. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bridgeport Public Library and Quarry Park are located nearby.
Fairfield Inn & Suites by Marriott Fairmont

Fairfield Inn & Suites by Marriott Fairmont

3 out of 5
Price was CA $2,423, price is now CA $2,393 per person
CA $2,393
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Morgantown (MGW)
Book a stay at this business-friendly hotel in Fairmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Middletown Mall and Valley Worlds of Fun are located nearby.

Top Oakland hotels deals

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy Oakland MD
Free cancellation
Reserve now, pay when you stay
The price is CA $146 per night
CA $146
CA $167 total
Aug 16 - Aug 17
includes taxes & fees
Stay at this motel in Oakland. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Broadford Park and Broadford Lake are located nearby.
Parking included
Free WiFi
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway Oakland MD
Free cancellation
Reserve now, pay when you stay
The price is CA $176 per night
CA $176
CA $200 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this motel in Oakland. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Deep Creek Lake and Deep Creek Lake State Park are located nearby.
Parking included
Free WiFi
That Special Place

That Special Place

Oakland MD
The price is CA $312 per night
CA $312
CA $673 total
Aug 31 - Sep 1
includes taxes & fees
Stay at this cabin in Oakland. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Deep Creek Lake and Deep Creek Lake State Park are located nearby.
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
Get rates
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Deep Creek Lake and Deep Creek Lake State Park are located nearby.
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
Get rates
Stay at this vacation home in Oakland. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Deep Creek Lake and Deep Creek Lake State Park are located nearby.
Kitchen
Washer
AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table, NEW FIRE PIT

AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table, NEW FIRE PIT

Oakland MD
Get rates
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Deep Creek Lake and Deep Creek Lake State Park are located nearby.
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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.

Stay near popular Oakland attractions

A waterfall cascading over a rocky cliff surrounded by lush greenery.

Swallow Falls State Park

9.8/10 (138 reviews)
You can take time to visit Swallow Falls State Park during your travels to Oakland. Stroll along the riverfront in this family-friendly area, or seek out the ski slopes.
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Oakland Vacations

Accidentally stumbling upon somewhere new is precisely what makes travel so special, But of course, it certainly never hurts to research a bit about the area before you set off. We'll get you up to speed on the basic facts about Oakland.

This town is located 130 miles (209 kilometers) to the west of Washington, the nation's lively capital. Keyser is a close-by significant area that's just 20 miles (32 kilometers) to the east.

2,000 friendly locals reside in this part of Maryland.

Places to visit in Oakland

Whether you're chasing powder or you just want to relax inside with a hot drink, book accommodation at Wisp Resort and experience their awesome amenities. Need more ideas? Being among nature is proven to enhance both your physical and spiritual well-being. Spend time at Cathedral State Park and enjoy the benefits of reconnecting with the natural environment. And there's more going on in the surrounding area. Dress in your finest khakis and reach for your lucky putter. If you're to itching to head outdoors for a day on the fairways, reserve a tee time at Thousand Acres Lakeside Golf Course.

Where do you fly into for Oakland?

Stow your tray table, fasten your seatbelt and get ready to say hello to Oakland! Once you disembark at Morgantown Municipal Airport (MGW), the bustling main streets will be just 35 miles (56 kilometers) to the southeast from here.

Frequently asked questions

How much are vacation packages to Oakland?
With vacation packages being sold for just CA $2,285, there's no need to blow out the credit card to travel to Oakland. Travelocity can help. Bundle up hotels, flights and experiences into a convenient package and land fantastic discounts. The more you book, the greater the savings.
How long should my Oakland vacation be?
If you need some guidance, most travelers spend roughly 2 nights in Oakland. But to uncover the true spirit of this destination, stay a little longer. That way you can cross off more attractions and really experience the local culture.
Where can I get the best vacation package deals for Oakland?
It's hard to top Travelocity when it comes to finding your Oakland package deal. There are as many as 400 airlines and 1,000,000 properties worldwide to choose from. Book your vacation now and get ready to cross another amazing destination off your list.
Why should I book my Oakland vacation package via Travelocity?
Whether you're planning a weeks-long vacation or a last-minute escape, we have many tempting destinations to choose from at a great price. In addition, we provide 24/7 support, superb service and a Price Match Guarantee. Save yourself money and time and book your dream vacation now.
Can I save on my Oakland car rental if I book it with my hotel or flight?
You certainly can — combine your car, flight and hotel into an Oakland vacation package and you'll save loads. With so much to see and do in Oakland, having your own wheels will come in handy. Once you've buckled yourself in, turn up the stereo and find your way to Monticello, an unmissable attraction around 177 kilometers from Oakland.
Which airport is best for Oakland?
One option is Morgantown Municipal Airport (MGW). From here, you'll have to travel southeast for roughly 48 kilometers to reach inner Oakland. Another possibility is North Central West Virginia Airport (CKB), 72 kilometers away from central Oakland.
What is there to do in Oakland?
While hopping off the tourist trail is no doubt rewarding, you shouldn't ignore the popular attractions that make a destination famous. Swallow Falls State Park and Herrington Manor State Park are just two of them in Oakland.
Where should I stay when visiting Oakland?
If you're looking for someplace comfortable to base yourself, check out the The Garrett Inn. It's the top choice for many visitors.

Photos of local treasures

Browse Oakland vacation photos for more inspiration

A river flowing through a forest with a waterfall.
A waterfall cascading down a rocky cliff surrounded by dense green foliage.
A frozen waterfall with icicles hanging from the edges.
A waterfall cascading down a rocky cliff surrounded by dense forest.
A waterfall cascading over rocks in a forested area.