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Find Family Hotels in Oakland, MD

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Check availability on Oakland Family Hotels

Our top choices for Oakland family-friendly hotels

Deluxe Suite | Private kitchen | Microwave, coffee/tea maker
Baja Motel

Baja Motel

2.0 star property
Oakland
8.8 out of 10, Excellent, (84)
"It was a nice place to stay for the night while traveling "
United States
William
Baja Motel
Game room
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!

2.0 star property
Oakland
10.0 out of 10, Exceptional, (12)
"Nothing negative to say. Beautiful place and friendly owner. Owner is accessible and very accommodating. "
United States
Sean
The price is SAR 807
SAR 2,704 total
includes taxes & fees
10 Dec - 11 Dec
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Fridge, microwave, oven, dishwasher
Cubs Den - Hot Tub- Walk to Lake-Fire Pit -Kayaks

Cubs Den - Hot Tub- Walk to Lake-Fire Pit -Kayaks

Oakland
9.0 out of 10, Wonderful, (9)
"We were very pleased with our"
United States
Inna D.
The price is SAR 428
SAR 2,100 total
includes taxes & fees
15 Dec - 16 Dec
Cubs Den - Hot Tub- Walk to Lake-Fire Pit -Kayaks
Game room
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!

Oakland
10.0 out of 10, Exceptional, (34)
"Great property, loved our stay here! We will definitely stay here again! "
United States
Shawnnelle H.
The price is SAR 692
SAR 2,409 total
includes taxes & fees
18 Dec - 19 Dec
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
3 bedrooms, desk, free WiFi, bed sheets
In the heart of Deep Creek Lake! - "Shamrock Inn"

In the heart of Deep Creek Lake! - "Shamrock Inn"

Mountainside
9.6 out of 10, Exceptional, (5)
"Place was absolutely gorgeous host was very accommodating. Can't say enough good things about it"
United States
Michael M.
The price is SAR 706
SAR 1,743 total
includes taxes & fees
10 Dec - 11 Dec
In the heart of Deep Creek Lake! - "Shamrock Inn"
A heated pool
Cove Creek Lodge: 215 Standard Double Queen Room

Cove Creek Lodge: 215 Standard Double Queen Room

2.0 star property
Oakland
10.0 out of 10, Exceptional, (2)
"It was very clean and the workers were so kind and was the perfect little get away for my family! "
United States
Chris
The price is SAR 891
SAR 1,146 total
includes taxes & fees
20 Dec - 21 Dec
Cove Creek Lodge: 215 Standard Double Queen Room
Exterior
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Oakland
10.0 out of 10, Exceptional, (4)
"The place was so clean and fully stocked. We had a wonderful stay. Five stars!! "
United States
Lori S.
The price is SAR 486
SAR 1,474 total
includes taxes & fees
21 Dec - 22 Dec
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Game room
Will O' The Wisp: 501F Three Bedroom/Two Bath

Will O' The Wisp: 501F Three Bedroom/Two Bath

Mountainside
10.0 out of 10, Exceptional, (1)
"Was a beautiful condo! We had a great time kids loved the beach area "
United States
Chelsy H.
The price is SAR 1,571
SAR 2,025 total
includes taxes & fees
19 Dec - 20 Dec
Will O' The Wisp: 501F Three Bedroom/Two Bath
Game room
Will O' The Wisp: 301D Two Bedroom/Two Bath

Will O' The Wisp: 301D Two Bedroom/Two Bath

Oakland
7.4 out of 10, Good, (3)
"Very easy to book. Room was clean and perfectly met my family's needs. Can't wait to go back."
United States
Jacquelyn P.
The price is SAR 1,433
SAR 1,828 total
includes taxes & fees
10 Dec - 11 Dec
Will O' The Wisp: 301D Two Bedroom/Two Bath
Indoor pool
Comfort Inn Grantsville-Deep Creek Lake

Comfort Inn Grantsville-Deep Creek Lake

2.5 star property
Grantsville
8.4 out of 10, Very Good, (714)
"Friendly staff, clean room"
United States
Linda
The price is SAR 399
SAR 455 total
includes taxes & fees
10 Dec - 11 Dec
Comfort Inn Grantsville-Deep Creek Lake
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.
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Top Oakland Hotel Reviews

The Garrett Inn

The Garrett Inn

10/10 Excellent
"Everything about the place was perfect, centrally located, clean and comfortable. The farmhouse kitcsh was a little overboard but the place was very nice and very clean! "
Karen 3-night trip
Posted 10 days ago
The Garrett Inn

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Frequently asked questions

What's Oakland like for family-friendly vacations?
The destination of Oakland is a great choice if you've been thinking about a vacation with your kids. The horseback riding, sledding, and camping sites are just a few things that make this an attractive vacation spot for families. Take to the air and fly into Morgantown, WV (MGW-Morgantown Municipal), which is located 31.8 mi (51.2 km) from the city center.
When's the best time to book a family-friendly vacation in Oakland?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Oakland are January, December, February, and May, with each month seeing an average of 31 inches of snowfall.
What's there to see and do with your family in Oakland?
Ruth Enlow Library of Garrett County, Wisp Resort, and Funland are interesting attractions you and your family will enjoy exploring while you are staying in Oakland. Make sure you have lots of time for activities like Adventure Sports Center International and Janet and Imre Szilagyi Center for the Visual and Performing Arts.