Oakland Vacation Packages 2026 from $2,550

Oakland flight + hotel vacation packages

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

St. Bart's Retreat

$2,550

per person

Feb 19 - Feb 21

found 5 hours ago

Roundtrip non-stop flight included

New York (JFK) to Morgantown (MGW)

A restaurant and a hot tub are featured at this vacation home. Guests will appreciate free perks like free self parking and WiFi in public areas.

Under the Stars

Mountainside

$4,341

per person

Feb 19 - Feb 21

found 5 hours 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.

VVS - Very Very Special

$3,267

per person

Feb 19 - Feb 21

found 5 hours ago

Roundtrip non-stop flight included

New York (JFK) to Morgantown (MGW)

A restaurant and a hot tub are featured at this vacation home. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are provided for your convenience.

Celebration at Deep Creek

$3,072

per person

Feb 19 - Feb 21

found 5 hours 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.

Ever After

$2,841

per person

Feb 19 - Feb 21

found 5 hours 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.

Top Oakland hotels deals

The Garrett Inn

17848 Garrett Highway Oakland MD

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$123 total

Jan 7 - Jan 8

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

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

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

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

Mt. Dew- AMAZING LAKE FRONT! 7 BR Home with Hot Tub, Fire Pit, Dock, Pool Table

Oakland MD

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A water park and a hot tub are featured at this smoke-free vacation home. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also provided.

Hot Tub

Kitchen

Amazing Central Location! Lakefront! Hot tub/dock!

Oakland MD

Get rates

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

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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 $2,550, 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.