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Find Hotels in Oakland, MD

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104b- Lakefront Condominium, one Bedroom, two Fireplaces & Flat Screen TV!
5/5Exceptional! (2 reviews)
Great Stay!

"Everything worked out great. Comfortable beds with plenty of blankets. Kitchen was well stocked. Shared pool and hot tub were great, although may have had a little too much chlorine. Great location."…"

Reviewed on Jan 30, 2019

104b- Lakefront Condominium, one Bedroom, two Fireplaces & Flat Screen TV!
Stunning log Home That Offers a Phenomenal Lake Front!
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9.5 mi from city center
4.3/5Excellent! (43 reviews)
Nice house on the water

"We enjoyed our week at Morningside Lodge! Nice backyard, although very steep incline from porch to middle of yard, would be nice to have steps/path built down to dock. It was very hard to keep the house cool, we always had to have fans running to keep air moving. It was nice to have 4 suites so each ..."…"

Reviewed on Jul 12, 2020

Stunning log Home That Offers a Phenomenal Lake Front!
Dogs Welcome! Lakefront Home W/private Indoor Pool, Private Dock, & Hot Tub!
4/5Very Good! (2 reviews)
Nice

"It was really a nice get away n clean"…"

Reviewed on Oct 18, 2018

Dogs Welcome! Lakefront Home W/private Indoor Pool, Private Dock, & Hot Tub!

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Cozy Cabin W/indoor Hot Tub, 2 Wood Fireplaces, & Foosball Table!
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8.82 mi from city center
5/5Exceptional! (8 reviews)
Lucky stars

"This was our first trip to Deep Creek Lake so we were unfamiliar with the area. This home had everything we needed and more. The property was conveniently located to attractions...grocery, restaurants & the lake. If we return to the area we’d like to find a property on the lake, but this house was ..."…"

Reviewed on Jul 25, 2020

Cozy Cabin W/indoor Hot Tub, 2 Wood Fireplaces, & Foosball Table!
DOG Welcome! Sandy Beach Lakefront W/private Dock, Hot Tub, & Fire Pit!
4.3/5Excellent! (4 reviews)
beautiful

"enjoyed our stay"…"

Reviewed on Mar 15, 2020

DOG Welcome! Sandy Beach Lakefront W/private Dock, Hot Tub, & Fire Pit!
Dogs Welcome! Log Home W/hot Tub, Fire Pit, & Summer State Park Access!
4.4/5Wonderful! (9 reviews)
Enjoyed our stay.

"Nice place in a quiet neighborhood, close to everything."…"

Reviewed on Sep 28, 2019

Dogs Welcome! Log Home W/hot Tub, Fire Pit, & Summer State Park Access!
Lakefront Home W/private Dock, Sun Room, & Tons of Community Amenities!
Wooded Lake Area Cabin W/hot Tub, Wood Fireplace, & Shuffleboard!
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8.78 mi from city center
4.7/5Exceptional! (7 reviews)
Birthday Getaway

"Had a great time! Close to everything. Loved the hot tub."…"

Reviewed on Dec 6, 2019

Wooded Lake Area Cabin W/hot Tub, Wood Fireplace, & Shuffleboard!
Lake Area Cabin W/hot Tub, Wood Fireplace, & Charcoal Grill!
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8.73 mi from city center
4.6/5Exceptional! (150 reviews)
Cabin Getaway

"Decided to head to the mountains with our 2 grandsons, ages 15 and 12. Perfect spot for base camp. Adults enjoyed downtime out on porch while boys were on phones. Such is life. Sofas a tad tired and sure good use a better mattress in master br but you get what you pay for and all was well. Was happy ..."…"

Reviewed on Jul 28, 2020

Lake Area Cabin W/hot Tub, Wood Fireplace, & Charcoal Grill!
Dogs Welcome! Lake Area Cabin W/hot Tub & Wood Fireplace!
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8.71 mi from city center
4.7/5Exceptional! (134 reviews)
oct 15to 18

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: ALL OF THE CABINS IN YELLOWSTONE VILLAGE ARE NICE ..."…"

Reviewed on Apr 24, 2020

Dogs Welcome! Lake Area Cabin W/hot Tub & Wood Fireplace!
Dogs Welcome! Lake Area Home W/hot Tub!
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8.71 mi from city center
4.6/5Exceptional! (190 reviews)
No Worries cabin

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a great long weekend at this charming cabin ..."…"

Reviewed on Apr 24, 2020

Dogs Welcome! Lake Area Home W/hot Tub!
Dogs Welcome! Lake Area Cabin W/hot Tub, Wood Fireplace, & Charcoal Grill!
4.8/5Exceptional! (67 reviews)
Railey did an incredible job. We left a vital item and got it back so fast during a tough time.

"Property is the perfect single family getaway. Even during the beginning of the quarantine, this respite away from the hustle bustle was essential to the family dynamic and we are so grateful to the community and general vibe, which all takes effort. What a great place. We will be back as soon as ..."…"

Reviewed on Mar 26, 2020

Dogs Welcome! Lake Area Cabin W/hot Tub, Wood Fireplace, & Charcoal Grill!
Inn At Deep Creek
2.5 out of 5
19638 Garrett Hwy, Oakland, MD
The price is $169 per night
8.54 mi from city center
4/5Very Good! (161 reviews)

"Nice lobby, clean room, comfortable bed. Only slight issue we had is the WiFi was weak in the room."…"

Reviewed on Jun 29, 2020

Inn At Deep Creek
Oak Mar Motel
2 out of 5
208 N 3rd Street, Oakland, MD
Free CancellationReserve now, pay when you stay
The price is $99 per night
1.82 mi from city center
4.4/5Excellent! (82 reviews)

"Very clean hotel with a convenient location in downtown Oakland. Front desk was very nice and helpful when we asked for more towels."…"

Reviewed on Jun 30, 2020

Oak Mar Motel
The Garrett Inn
2.5 out of 5
17848 Garrett Highway, Oakland, MD
The price is $100 per night
6.95 mi from city center
4.8/5Exceptional! (149 reviews)

"We liked that it was close to all the attractions we wanted to go. The bed could have been more comfortable."…"

Reviewed on Jul 26, 2020

The Garrett Inn
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Visiting Oakland

Visitors to Oakland are sure to enjoy the lakeside setting. Tourists can also enjoy the city's ski areas and ecotours.

  • You'll find 797 Expedia hotels and other accommodations in the larger area of Cumberland
  • The closest major airport is in Morgantown, WV (MGW-Morgantown Municipal), 33.3 mi (53.6 km) from the city center
  • The next closest is in Elkins, WV (EKN-Randolph County), 42.8 mi (68.9 km) away

Sightseeing and Staying in Oakland

The city's natural setting is picturesque, including the lakeside and Deep Creek Lake. In the area, you'll also find Cathedral State Park and Thousand Acres Lakeside Golf Course.

In Oakland, you'll be able to select from 362 hotels and other lodging options so you'll have a variety of choices for a perfect holiday retreat. Below are top ranked ones based on our user reviews:

  • The Garrett Inn - Amenities at this 2.5-star motel include free parking and free WiFi. It's a favorite with Expedia travelers for its central location and WiFi.
  • Oak Mar Motel - Our customers like the dining options and breakfast at this motel. With a stay at this 2-star motel, guests can enjoy access to a restaurant and free parking, along with free WiFi.
  • Haley Farm Bed & Breakfast - With a stay at this 3-star bed & breakfast, guests can enjoy access to free breakfast and free parking, along with free WiFi.

Dressing for Oakland

  • Between January and March, you can expect average temperatures of 52°F during the day and 17°F at night
  • From April to June, the average during the day is 78°F, while the average at night is 31°F
  • July through September has daytime averages of 79°F with nighttime averages of 46°F
  • In October-December, you can expect daytime averages of 64°F and nighttime averages of 18°F
  • Oakland gets about 50.16 inches of rain per year
  • Usually August and July are the hottest months with an average of 78°F, whereas January and December are often coldest, averaging 19°F

Frequently asked questions

What's the best place to stay in Oakland?
The Garrett Inn is ranked highly by Expedia customers. This property offers free WiFi and free parking. Reviews from our site also recommend Oak Mar Motel and Inn At Deep Creek as top choices for your trip.
If I need to cancel my hotel reservation in Oakland, will I receive a refund?
Yes! The majority of hotel reservations are fully refundable if cancelled prior to the accommodation’s cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of booking. Put your dates in and click on “Search”, then you can use the “free cancellation” filter to view the best deals in Oakland.
Where can I learn more about changing or cancelling my trip to Oakland?
To access more information about rescheduling or cancelling your trip to Oakland, head over to our customer service page.
What's the best place to stay for families in Oakland?
Oak Mar Motel is a property with a restaurant and free parking, and it’s a top choice on Expedia for families. Other good choices for your kid-friendly vacation include The Garrett Inn and Inn At Deep Creek.
What's the best pet-friendly hotel in Oakland?
Inn At Deep Creek is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and free WiFi for its human guests.
What's the best place to stay with easy access to Deep Creek Lake?
Inn At Deep Creek is one of the top choices for your stay based on our traveler data, and this hotel offers an outdoor pool and free WiFi. It’s located just a short 0.6 mi (0.9 km) from Deep Creek Lake.
What about the best place to stay close to Swallow Falls State Park?
One of the top choices for your stay is Alpine Lake Resort, located 2.6 mi (4.3 km) from Swallow Falls State Park, and this 3-star lodge offers a golf course and a restaurant. Oak Mar Motel and 3bedroom 3.5baths Sleeps 6 are other good choices within 5 miles.
What's the best hotel to stay near the slopes in Oakland?
Based on our travel data, Inn At Deep Creek is a top hotel for hitting the ski slopes, and features free WiFi and free parking. Those looking to ski or snowboard can spend their days at Wisp Resort.
What are some accommodations with pools in Oakland?
Inn At Deep Creek is a top hotel with a children’s pool, a seasonal outdoor pool, and free WiFi.

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