Deals on vacations and trips to Oakland

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Oakland flight + hotel vacation packages

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

Cannon Hill Inn

2 out of 5
Price was $1,056, price is now $982 per person
$982
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Morgantown (MGW)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A virtual front desk are provided for your convenience.
La Quinta Inn & Suites by Wyndham Morgantown

La Quinta Inn & Suites by Wyndham Morgantown

3 out of 5
Price was $1,284, price is now $1,205 per person
$1,205
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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 buffet breakfast and free self parking.
Hampton Inn & Suites Morgantown / University Town Centre

Hampton Inn & Suites Morgantown / University Town Centre

2.5 out of 5
Price was $1,299, price is now $1,231 per person
$1,231
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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.
Sonesta Essential Morgantown

Sonesta Essential Morgantown

2.5 out of 5
Price was $1,105, price is now $1,048 per person
$1,048
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Morgantown (MGW)
This hotel doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A computer station is provided and the front desk is staffed around-the-clock.
Lakeview Golf Resort

Lakeview Golf Resort

3.5 out of 5
Price was $1,045, price is now $991 per person
$991
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Morgantown (MGW)
A golf course and a gym are featured at this smoke-free resort. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, a library, and dry cleaning are also on offer.

Top Oakland hotels deals

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy Oakland MD
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $119 total per night
$119 total
Sep 30 - Oct 1
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

The Garrett Inn

2.5 out of 5
17848 Garrett Highway Oakland MD
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $144 total per night
$144 total
Sep 1 - Sep 2
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

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
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,

Oakland MD
Get rates
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Oakland MD
Get rates
A hot tub is featured at this cabin, along with laundry facilities.
Hot Tub
Kitchen
The winter is coming !!!

The winter is coming !!!

Oakland MD
$416 nightly
The price is $441 total per night
$441 total
Sep 1 - Sep 2
Total with taxes and fees
A hot tub is featured at this cabin, along with laundry facilities.
Hot Tub
Kitchen
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See all available properties in Oakland
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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.

Stay near popular Oakland attractions

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

Swallow Falls State Park

9.8/10 (138 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.
See properties

Frequently asked questions

How much are vacation packages to Oakland?
With vacation packages being sold for just $982, 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.

Photos of local treasures

Browse Oakland vacation photos for more inspiration

A river flowing through a forest with a waterfall.
A waterfall cascading down a rocky cliff surrounded by dense green foliage.
A frozen waterfall with icicles hanging from the edges.
A waterfall cascading down a rocky cliff surrounded by dense forest.
A waterfall cascading over rocks in a forested area.