Book Exclusive Oakland Vacation Packages

Choose one or more items to build your trip:

Oakland flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Cannon Hill Inn

Cannon Hill Inn

4 out of 5
per person
Apr. 3 - Apr. 7
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Morgantown (MGW)
Stay at this 4-star inn in Rowlesburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Janet and Imre Szilagyi Center for the Visual and Performing Arts and Cannon Hill are located nearby.
Hampton Inn & Suites Morgantown / University Town Centre

Hampton Inn & Suites Morgantown / University Town Centre

2.5 out of 5
per person
Apr. 3 - Apr. 7
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Morgantown (MGW)
Book a stay at this business-friendly hotel in Morgantown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Monongalia County Ballpark and Dick Dlesk Soccer Stadium are located nearby.
La Quinta Inn & Suites by Wyndham Morgantown

La Quinta Inn & Suites by Wyndham Morgantown

2.5 out of 5
per person
Apr. 3 - Apr. 7
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Morgantown (MGW)
Book a stay at this business-friendly hotel in Morgantown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions University Town Center and Earl L. Core Arboretum are located nearby.
Lakeview Golf Resort

Lakeview Golf Resort

3.5 out of 5
per person
Apr. 3 - Apr. 7
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Morgantown (MGW)
Stay at this 3.5-star golf resort in Morgantown. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions Lakeview Resort Golf Course and West Virginia Botanic Garden are located nearby.
Hotel Morgan a Wyndham Hotel

Hotel Morgan a Wyndham Hotel

3.5 out of 5
per person
Apr. 3 - Apr. 7
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Morgantown (MGW)
Stay at this 3.5-star business-friendly hotel in Morgantown. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Morgantown Farmers Market and Mountaineer Field are located nearby.

Top Oakland hotels deals

Riverside Suites

Riverside Suites

2 out of 5
1501 Maryland Hwy, Oakland, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $153 per night
CA $153
CA $175 total
includes taxes & fees
14 Mar - 15 Mar
Stay at this motel in Oakland. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Broadford Park and Broadford Recreation Area are located nearby.
Parking included
Free WiFi
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,

Get rates
Stay at this vacation home in Oakland. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Deep Creek Lake and Wisp Resort are located nearby.
Kitchen
Washer
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 $143 per night
CA $143
CA $163 total
includes taxes & fees
2 Mar - 3 Mar
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 Wisp Resort are located nearby.
Modern house on the lake with private dock, hot tub, air hockey & central AC

Modern house on the lake with private dock, hot tub, air hockey & central AC

Get rates
Stay at this vacation home in Oakland. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Deep Creek Lake and Deep Creek Lake State Park are located nearby.
Hot tub
Kitchen
Bright condo with Deep Creek Lake views, wood fireplace

Bright condo with Deep Creek Lake views, wood fireplace

Get rates
Stay at this condo in Oakland. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Deep Creek Lake and Deep Creek Lake State Park are located nearby.
Kitchen
Washer
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

Get rates
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Deep Creek Lake and Deep Creek Lake State Park are located nearby.
Hot tub
Kitchen
Don't see what you're looking for?
See all available properties in Oakland
View all properties
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

Swallow Falls State Park

Swallow Falls State Park

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.

Swallow Falls State Park
Herrington Manor State Park

Herrington Manor State Park

You can take time to visit Herrington Manor State Park during your travels to Oakland. While you're in the area, stroll along the lakeside.

Herrington Manor State Park

Garrett Regional Medical Center

Though Garrett Regional Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Oakland while you are here.

Garrett Regional Medical Center

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 $859, 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

Photo by KM Moore
Photo by KM Moore
Photo by Tash Foe
Photo by Tash Foe
Photo by Rachel Drury
Photo by Rachel Drury
Photo by Shelly Sisler
Photo by Shelly Sisler
Photo by Laura
Photo by Laura