Book Hotels in Oakland, MD

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Top Oakland hotels

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Oakland
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Great location, property, house and owner communication - would definitely stay there again!

Reviewed on Oct 23, 2025

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Opens in a new windowLakefront, dog friendly, dock slip, hot tub, and fire pit
Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

Oakland
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 ...
Beautiful house and property, grandkids loved fishing off the dock, the fire pit and hot tub were big hits . Would go back again, house was very accommodating to our large group. Thank you

Reviewed on Sep 1, 2025

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Opens in a new windowStunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

2 out of 5
Oakland
$641 nightly
The price is $725 total per night from Nov 10 to Nov 11
$725 total
Nov 10 - Nov 11
Total with taxes and fees
This cabin features a gym and a hot tub. Families will appreciate the arcade/game room and onsite laundry facilities. A garden and barbecue grills are also ...
Great spot for a team retreat!

Reviewed on Oct 10, 2025

Opens in a new windowNew Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Oakland
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Great place! Lots of space for our kids and dog. Really enjoyed the firepit, games, and comfortable beds. Check in and out was very easy. Would definitely book again.

Reviewed on Oct 20, 2025

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Opens in a new windowGathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
Level lakefront, family-friendly, hot tub, low fees, private dock

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

Oakland
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, ...
Great house, attentive host. Lake access, hot tub, great bar / pool table room, fire pit. I was there with friends but also noticed it was well configured for families.

Reviewed on Oct 1, 2025

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Opens in a new windowLevel lakefront, family-friendly, hot tub, low fees, private dock
Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

Oakland
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.
We had a wonderful time at the lake loft. Great time with friends in a lovely home. Everything was clean and the beds were comfy--and an incredible outdoor setup

Reviewed on Oct 20, 2025

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Opens in a new windowLakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway, Oakland, MD
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $123 total per night from Nov 10 to Nov 11
$123 total
Nov 10 - Nov 11
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.
We have stayed here numerous times over the past 10 years. The Garrett Inn has always been a pleasure, clean rooms, affordable rates and a friendly and welcoming staff.

Reviewed on Nov 3, 2025

Opens in a new windowThe Garrett Inn
Amazing Central Location! Lakefront! Hot tub/dock!

Amazing Central Location! Lakefront! Hot tub/dock!

Oakland
A hot tub is featured at this vacation home, along with laundry facilities and concierge services. Barbecue grills are provided for your convenience.
Great property. Well-equipped for large families.

Reviewed on Oct 13, 2025

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Opens in a new windowAmazing Central Location! Lakefront! Hot tub/dock!
Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy, Oakland, MD
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
Cute little motel
Super cute outside! Clean room, dated. TV took a bit to get set up. Fridge was good. Sleep was not the best. We had noisy late night guests above us until about 2:30. A train came by overnight and honked twice. The road noise settles down late.

Reviewed on Oct 20, 2025

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Opens in a new windowBaja Motel
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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.

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?
From cool amenities to bigger rooms, kid-friendly hotels come with features that can help transform a routine family vacation into a sensational one. These Oakland properties make traveling with little ones a breeze: Your gang will enjoy their time at Swimming Bear Lodge. A nearby beach and a fireplace are just a few of the things that help make this hotel an attractive option. Unreel is another top pick. After an exciting day of sightseeing, come back home to your cozy room and perks like a fireplace and a barbecue grill.
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 $123. 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 894 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 January, April and May. If you'd prefer the peace of off-season, book a stay during quieter months, such as July, August and December.
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

Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

5 out of 5
Posted 5 days ago
Travelocity Verified Review
"Great with communication "
A verified traveler stayed at Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

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