Oakland Vacation Packages 2025/2026 from $174

Oakland flight + hotel vacation packages

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

Euro Suites Hotel

Save 100% on your flight

$174

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Morgantown (MGW)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy free perks like free self parking and an area shuttle.

Laurel River Club Bed & Breakfast

Save 100% on your flight

$276

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Morgantown (MGW)

A sauna, free self parking, and a virtual front desk are featured at this bed & breakfast. Enjoy the free full breakfast each morning. A coffee shop, a garden, and a picnic area are also on offer.

Hampton Inn & Suites Morgantown / University Town Centre

Save 100% on your flight

$228

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Morgantown (MGW)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Lakeview Golf Resort

$226

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Morgantown (MGW)

A golf course and an indoor pool are featured at this smoke-free resort. Enjoy the gym and perks like free self parking and free WiFi. There's a restaurant and a bar/lounge for dining and drinks, and also a sauna on site.

Hotel Morgan a Wyndham Hotel

$252

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Morgantown (MGW)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a business center, and a coffee shop are also offered.

Top Oakland hotels deals

The Garrett Inn

17848 Garrett Highway Oakland MD

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$101 total

Nov 23 - Nov 24

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and express check-in are also on offer.

Parking included

Free WiFi

Baja Motel

1501 Maryland Hwy Oakland MD

Get rates

Free WiFi in public areas is available at this motel. Take advantage of the free self parking.

Parking included

Free WiFi

Amazing Central Location! Lakefront! Hot tub/dock!

Oakland MD

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A hot tub is featured at this vacation home, along with laundry facilities and concierge services. Barbecue grills are provided for your convenience.

Hot Tub

Kitchen

Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

Oakland MD

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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.

Hot Tub

Kitchen

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

Oakland MD

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A hot tub is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.

Hot Tub

Kitchen

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

Oakland MD

$644 nightly

$729 total

Dec 3 - Dec 4

Total with taxes and fees

This cabin features a gym and a hot tub. Families will appreciate the arcade/game room and onsite laundry facilities. A garden and barbecue grills are also provided.

Hot Tub

Kitchen

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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.

Popular places to visit

Gorgeous fall day! Lots of people, but there was room to walk

Swallow Falls State Park

5/5(29 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.

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.

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.

Frequently asked questions

How much are vacation packages to Oakland?

With vacation packages being sold for just $174, 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 110 mi 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 30 mi to reach inner Oakland. Another possibility is North Central West Virginia Airport (CKB), 45 mi 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.