Book Hotels in Oakland, Maryland

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Nov 27 - Nov 28
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Nov 28 - Nov 29
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Dec 2 - Dec 4

Most frequently booked Oakland hotels

Inn At Deep Creek

Inn At Deep Creek

2.5 out of 5
19638 Garrett Hwy, Oakland, MD, 21550
Free Cancellation
Reserve now, pay when you stay
7.79 mi from city center
The price is $119 per night
$119
per night
Nov 28 - Nov 29
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free Internet in public areas. There's a seasonal outdoor pool on site, and laundry facilities and concierge services are also offered.
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway, Oakland, MD, 21550
6.1 mi from city center
The price is $94 per night
$94
per night
Nov 28 - Nov 29
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Suites at Silver Tree A124

Suites at Silver Tree A124

3.5 out of 5
Oakland, MD
8.03 mi from city center
The price is $106 per night
$106
per night
Nov 28 - Nov 29
Free WiFi in public areas is available at this condo. Take advantage of the free self parking.
The Haven 8 Bedroom House

The Haven 8 Bedroom House

4 out of 5
1131 Lake Shore Drive, Oakland, MD, 21550
7.24 mi from city center
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This vacation home features an outdoor pool and an indoor pool. Enjoy the spa tub and perks like free self parking. Barbecue grills are provided for your convenience.
Johnny Appleseed

Johnny Appleseed

3.5 out of 5
159 Sorbus Lane, Oakland, MD, 21550
7.51 mi from city center
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This vacation home features an outdoor pool and an indoor pool. Free self parking and barbecue grills are also offered on site.
Home Sweet Cabin 4 Bedroom House

Home Sweet Cabin 4 Bedroom House

3.5 out of 5
350 Maple Del Lane, Oakland, MD, 21550
6.41 mi from city center
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A spa tub is featured at this cabin, along with barbecue grills. Take advantage of the free self parking.
Bear Feet 3 Bedroom Townhome

Bear Feet 3 Bedroom Townhome

3.5 out of 5
74 Timberloft Lane #9, Oakland, MD, 21550
8.35 mi from city center
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This apartment features a gym and a spa tub. Free self parking and barbecue grills are also offered on site.
Sunset Delight 9 Bedroom House

Sunset Delight 9 Bedroom House

3.5 out of 5
25 Old Chestnut Drive, Oakland, MD, 21550
8.23 mi from city center
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A spa tub is featured at this vacation home, along with barbecue grills. Take advantage of the free self parking.
Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!

Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!

Oakland, MD
2.41 mi from city center
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This vacation home features an indoor pool and a spa tub. Concierge services and barbecue grills are also provided.
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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.

Top family friendly Oakland hotel deals

Top hotels in Oakland for Extended Stay

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.

Seize your some day

Oakland Hotel & Travel Guide\n

Oakland currently has no Travelocity accommodations itself. That said, there are no less than 2 places to rest an easy drive away.

The Inn At Deep Creek, Maryland, which is the nearest Travelocity-listed hotel, is located 9 miles (14 kilometers) from central Oakland. For an alternative, why not have a look at the Quality Inn Deep Creek Lake, located in Maryland, which is 12 miles (20 kilometers) outside of the city center.

20 miles (32 kilometers) away from the city center of Oakland, you will find the Microtel Inn & Suites by Wyndham Hazelton/Bruceton Mills. The The Lodges at Sunset Village is 12 miles (19 kilometers) away. The Blue Moon Rising along with the Alpine Lake Resort are two other Travelocity-listed places to base yourself in Oakland.

For those longing to see more of the mountains that are found in this part of the country, you could also plan some extra days in other destinations in Western Maryland. Wise travelers should explore regional places of interest or try your luck at cross-country skiing before you check in to a local Travelocity-listed room.

The closest accommodation options in Cumberland are Frostburg and Historic Downtown Cumberland. Frostburg is 30 miles (48 kilometers) to the northeast of Oakland, while Historic Downtown Cumberland is 40 miles (61 kilometers) to the northeast. Travelocity-registered hotels in Frostburg are the Hampton Inn Frostburg and Quality Inn & Suites. The Fairfield Inn & Suites by Marriott Cumberland and Ramada Cumberland Downtown are a selection of the Travelocity-registered places to stay in Historic Downtown Cumberland.

Why not spend an afternoon cheering along with excited lovers of sports at an exciting match. You'll find Mountaineer Field 35 miles (56 kilometers) to the northwest of Oakland. Anybody that need to find a hotel near the stadium can take their choice from the The Chestnut Boutique Hotel or the Residence Inn by Marriott Morgantown.

Morgantown Municipal Airport is a primary arrival point for flights, and is found 35 miles (54 kilometers) from Oakland's downtown area. Nearby accommodation options include Holiday Inn Express Morgantown and Euro Suites Hotel.

Frequently asked questions

What are the top kid-friendly hotels in Oakland?
Take some of the challenges out of traveling with kids by choosing a family-friendly Oakland hotel. From fun amenities to additional services, these properties come with perks that’ll make your getaway an effortless one: Cozy Cabin w/Indoor Hot Tub, 2 Wood Fireplaces, Foosball Table, & Central A/C! will help make your break the most memorable one yet. It comes with plenty of nice little touches, such as a fireplace and a king bed. Oak Mar Motel is another great choice. After a fun day of exploring, come home to your comfortable room and amenities like a fridge and a microwave oven.
Where can I find cheap hotels in Oakland?
At Travelocity you’ll find really nice hotels in Oakland at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Oakland rather than in Oakland. We may find you even better rates, too.
How do I find the best Oakland hotel deals?
Simple! On Travelocity, look through the fantastic offers we’ve already found in Oakland then use our filters to find a great deal that’s perfect for you. Enter your travel dates, select the number of rooms you need, and we’ll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Oakland?
The cheapest hotel in Oakland is $87. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel’s location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Oakland?
There are 807 hotels in Oakland on Travelocity.
What are the best hotels in Oakland?
Oakland has so many great hotels to choose from at Travelocity — and it’s so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Oakland for you!
When is the best time to visit Oakland?
If you want the joy of a fun-filled trip in peak season, visit Oakland during . If you’d prefer the peace of off-season, book a stay during quieter months, such as .
When is the cheapest time to stay in Oakland?
Based on historic data is usually the cheapest month to visit Oakland. However, we have incredible deals all year round, so we’re confident you’ll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Oakland?
There are multiple hotels in Oakland that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We’ve got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Oakland. We have plenty of kid-friendly hotels in Oakland to choose from on Travelocity!
Why book a hotel in Oakland through Travelocity?
Because we have the top hotels in Oakland! We want to help you travel more and worry less. That’s why we’ve put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you’re getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Oakland on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Oakland hotel reviews by fellow wanderers

  • Inn At Deep Creek

    Inn At Deep Creek

    5 out of 5
    Posted 13 days ago
    travelocity Verified Review
    "This place was beautiful!! Great location as well!! I’ve already started making plans with friends do go back and show it off to others. This place is just cozy and inviting. I can’t say enough to how fantastic of a find this place is. Don’t hesitate. Don’t second guess. You won’t be disappointed. "
    A verified traveler stayed at Inn At Deep Creek
    Inn At Deep Creek