Title: Book the Best Oakland FAMILY FRIENDLY Hotels from CA $181 - Kid-Friendly Hotels in Oakland, MD | Expedia.ca [Hotels in Oakland](https://expedia.ca/Oakland-Hotels.d9160.Travel-Guide-Hotels)[Vacation Rentals in Oakland](https://expedia.ca/Oakland-Vacation-Rentals.d9160.Travel-Guide-VacationRentals)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d9160.Car-Rental-Guide)[Oakland Vacation Packages](https://expedia.ca/Oakland.d9160.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/6688cb44f390170dde19d3839b293328.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by KM Moore # Find Family Hotels in Oakland, MD from CA $181 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Oakland Family Hotels Tonight [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-09-29&endDate=2025-09-30&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-09-30&endDate=2025-10-01&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-03&endDate=2025-10-05&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Family Hotels ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/1400/1347/f842eceb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1347/99b644e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1400/1347/12a5bf31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1347/d44865a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Grantsville-Deep Creek Lake Grantsville 8.4/10 Very good (691) "Family friendly. Easy access to interstate" CA $159 CA $181 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Cumberland-Hotels-Comfort-Inn-Grantsville.h1347.Hotel-Information) ![Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/5000000/4150000/4144900/4144866/b098b312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4150000/4144900/4144866/e1aaa3f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/5000000/4150000/4144900/4144866/6c2dee5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4150000/4144900/4144866/w3837h2557x3y3-65d16e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SureStay Plus Hotel by Best Western Keyser Keyser 8.8/10 Excellent (528) "Staff was great! " CA $171 CA $192 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Keyser-Hotels-SureStay-Plus-Hotel-By-Best-Western-Keyser.h4144866.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9720000/9711400/9711388/99f0eeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Local cuisine](https://images.trvl-media.com/lodging/10000000/9720000/9711400/9711388/e8351a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Bungalow, 1 Bedroom](https://images.trvl-media.com/lodging/10000000/9720000/9711400/9711388/0296aa75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9720000/9711400/9711388/e27cccef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Homestead Guest House Reedsville 9.0/10 Wonderful (41) "Quiet and quaint for a true WV country feel. Close to WVU without the hustle and bustle of being downtown. Check in and check out were hassle free and easy. Great communication from the owners. Little cafe across the street is lovely. Had a wonderful experience and will definitely stay here again!" CA $179 CA $192 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Morgantown-Hotels-Modern-Homestead-Guest-House.h9711388.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/107000000/106260000/106251600/106251530/8afacd3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/107000000/106260000/106251600/106251530/88b8da13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106260000/106251600/106251530/21f8f80e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106260000/106251600/106251530/07ac3aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp! Oakland 10/10 Exceptional (8) "Nothing negative to say. Beautiful place and friendly owner. Owner is accessible and very accommodating. " CA $312 CA $1,026 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Oakland-Hotels-New-Listing-Victory-Cabin-Spacious.h106251530.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/5ce2b5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/1f9afee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/be49f9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video-game console, DVD player](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/da0ce863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger! Oakland 10/10 Exceptional (30) "We LOVED the house! Clean, cozy, great little town. Couldn’t ask for better hosts!" CA $187 CA $811 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Oakland-Hotels-Unwind-At-Jamesons-Cabin-Pet-Friendly.h91123713.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/106000000/105650000/105641600/105641553/dd1f53ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105650000/105641600/105641553/89df50c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105650000/105641600/105641553/ca82ac9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, foosball](https://images.trvl-media.com/lodging/106000000/105650000/105641600/105641553/6ac84ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger! Oakland 10/10 Exceptional (16) "We rented " CA $249 CA $974 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Oakland-Hotels-Cozy-Lake-Area-Cabin-Pet-Friendly-EV-Charger.h105641553.Hotel-Information) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102130000/102120300/102120259/w1287h858x1y1-93f76b5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games](https://images.trvl-media.com/lodging/103000000/102130000/102120300/102120259/w1287h858x1y1-aa7e85fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102130000/102120300/102120259/w1287h858x1y1-931787ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102130000/102120300/102120259/w1287h858x1y1-7622c5b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### In the heart of Deep Creek Lake! - "Shamrock Inn" Mountainside 9.6/10 Exceptional (5) "Place was absolutely gorgeous host was very accommodating. Can't say enough good things about it" CA $262 CA $652 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Oakland-Hotels-In-The-Heart-Of-Deep-Creek-Lake-Shamrock-Inn.h102120259.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/116000000/115770000/115760100/115760069/2c6e31e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115770000/115760100/115760069/485d7b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115770000/115760100/115760069/8f9fd4b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115770000/115760100/115760069/86d18cf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private & Spacious 8-bedroom lodge with amazing outdoor space and game room Oakland CA $1,315 CA $2,351 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Oakland-Hotels-Private-Spacious-8-Bedroom-Lodge-With-Amazing-Outdoor-Space-And-Game-Room.h115760069.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/cd4bfe55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/d313359f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/176bea50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/b5edd8d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Board Room-Enchanted Table Meadow. Near Deep Creek Lake & Wisp! Forest View! Accident 9.6/10 Exceptional (73) "Lovely quiet retreat. Comfortable, spacious, and nicely decorated " CA $113 CA $297 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Cumberland-Hotels-The-Board-Room-Enchanted-Table-Meadow-Near-Deep-Creek-Lake-Wisp-Forest-View.h49184146.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/104000000/103590000/103584700/103584616/4c0938dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103590000/103584700/103584616/cde1acb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/104000000/103590000/103584700/103584616/d3d34e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/104000000/103590000/103584700/103584616/0dfaa14e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Home in Garrett County, surrounded by trees, fields and farmland. Grantsville 10/10 Exceptional (37) "We enjoyed our overnight stay here! It’s was clean, plenty of space, cows, creek, and a beautiful starry sky!" CA $208 CA $378 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Grantsville-Hotels-Private-Home-In-Garrett-County.h103584616.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-14&endDate=2025-10-15®ionId=9160&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Oakland Hotel Reviews ![The Garrett Inn](//images.trvl-media.com/lodging/15000000/14920000/14910400/14910340/d2b2d172_y.jpg) ### The Garrett Inn 10/10 Excellent "Safe, quiet, clean, and adorable. " [](https://expedia.ca/Cumberland-Hotels-The-Garrett-Inn.h14910340.Hotel-Information) ## 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. 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