Oakland Vacation Packages 2026 from $2,395

Oakland flight + hotel vacation packages

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

Lasting Impressions

$2,395

per person

Apr 6 - Apr 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Morgantown (MGW)

A restaurant and a hot tub are featured at this vacation home. WiFi in public areas is free.

Under the Stars

Mountainside

$5,746

per person

Apr 6 - Apr 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Morgantown (MGW)

This smoke-free cabin features 2 hot tubs, an indoor pool, and a restaurant. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Barbecue grills are provided for your convenience.

Celebration at Deep Creek

$4,282

per person

Apr 6 - Apr 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Morgantown (MGW)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A restaurant is also provided.

Bear Hollow Lodge by Taylor Made Deep Creek

$2,741

per person

Apr 6 - Apr 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Morgantown (MGW)

This vacation home features a restaurant, free WiFi in public areas, and barbecue grills.

Owl Be Back

$2,501

per person

Apr 6 - Apr 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Morgantown (MGW)

A restaurant and free WiFi in public areas are featured at this vacation home.

Top Oakland hotels deals

The Garrett Inn

17848 Garrett Highway Oakland MD

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$123 total

Mar 8 - Mar 9

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

Get rates

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

Baja Motel

1501 Maryland Hwy Oakland MD

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$143 total

Mar 7 - Mar 8

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 winter is coming !!!

Oakland MD

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A hot tub is featured at this cabin, along with laundry facilities.

Hot Tub

Kitchen

Level lakefront, family-friendly, hot tub, low fees, private dock

Oakland MD

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A hot tub is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.

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

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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

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 $2,395, 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.