Oakland Vacation Packages 2026 from $869

Oakland flight + hotel vacation packages

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

Super 8 by Wyndham Fairmont

$869

per person

Sep 16 - Sep 20

found 24 hours ago

Roundtrip non-stop flight included

Greenville (GSP) to Morgantown (MGW)

This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A fireplace in the lobby and a picnic area are also provided.

Sonesta Essential Fairmont

$874

per person

Sep 16 - Sep 20

found 24 hours ago

Roundtrip non-stop flight included

Greenville (GSP) to Morgantown (MGW)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the business center, laundry service, and conference space. There's a gym on site, and a 24-hour front desk and a picnic area are also provided.

Best Western Plus Bridgeport Inn

$965

per person

Sep 16 - Sep 20

found 24 hours ago

Roundtrip non-stop flight included

Greenville (GSP) to Morgantown (MGW)

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

Holiday Inn Express & Suites Bridgeport by IHG

$1,026

per person

Sep 16 - Sep 20

found 24 hours ago

Roundtrip non-stop flight included

Greenville (GSP) to Morgantown (MGW)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.

Wingate by Wyndham Bridgeport/Clarksburg

$969

per person

Sep 16 - Sep 20

found 24 hours ago

Roundtrip non-stop flight included

Greenville (GSP) to Morgantown (MGW)

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

Top Oakland hotels deals

Baja Motel

1501 Maryland Hwy Oakland MD

$109 nightly

$124 total

Jul 9 - Jul 10

Total with taxes and fees

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

Parking included

Free WiFi

The Garrett Inn

17848 Garrett Highway Oakland MD

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$142 total

Jun 28 - Jun 29

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

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

Oakland MD

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This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden and barbecue grills are also provided.

Hot Tub

Kitchen

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Oakland MD

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This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Mc Henry 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/Dock/Amazing views HotTub

Oakland MD

$1,216 nightly

$1,374 total

Jul 1 - Jul 2

Total with taxes and fees

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

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

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

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.

A log cabin with a stone chimney, surrounded by snow-covered ground and trees.

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.

Lower Deep Creek Heritage Conservation Fund Site

You can take time to visit Lower Deep Creek Heritage Conservation Fund Site during your travels to Oakland. While you're in the area, stroll along the lakeside.

Frequently asked questions

How much are vacation packages to Oakland?

With vacation packages being sold for just $869, 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.