Title: Book the Best Oakland FAMILY FRIENDLY Hotels from CA $170 - 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 $170 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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 [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-15&endDate=2025-10-16&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-16&endDate=2025-10-17&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-24&endDate=2025-10-26&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Family Hotels ![Exterior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/d68aefb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/067bcc9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/b7ecb6ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/4e8ed583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats. Oakland 10/10 Exceptional (3) "The place was so clean and fully stocked. We had a wonderful stay. Five stars!! " CA $137 CA $492 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Oakland-Hotels-Lake-Views-HOT-TUB-Central-Location-Walk-To-Coffee.h115182127.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) ![Exterior](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/a46aee5d.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) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/1f9afee2.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 (31) "We LOVED the house! Clean, cozy, great little town. Couldn’t ask for better hosts!" CA $205 CA $822 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Oakland-Hotels-Unwind-At-Jamesons-Cabin-Pet-Friendly.h91123713.Hotel-Information) ![Children's area](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/9bf21fe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/1bbbf0db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/7ca08395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/c6c26a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wooded Retreat w Hot Tub, Loft, Game Room & Sauna Oakland 10/10 Exceptional (1) "Wonderful place for the perfect getaway! Just like the photos definitely worth every penny. Just have in mind that you are in the woods so the bugs are inevitable but the inside of the place was very clean.Me and my family took advantage of all the amenities from the grill, hot tub, fire place. Don't think twice and book this place!" [](https://www.expedia.ca/Oakland-Hotels-Wooded-Retreat-W-Hot-Tub.h115059189.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106260000/106251600/106251530/98df61f3.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) ![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) ### 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 $314 CA $1,033 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/106000000/105650000/105641600/105641553/dd1f53ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105650000/105641600/105641553/f42198b8.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) ![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) ### Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger! Oakland 10/10 Exceptional (16) "We rented " CA $252 CA $972 total includes taxes & fees Oct 29 - Oct 30 [](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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102130000/102120300/102120259/a012a856.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 $285 CA $665 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Oakland-Hotels-In-The-Heart-Of-Deep-Creek-Lake-Shamrock-Inn.h102120259.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91910000/91907800/91907749/2b163960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91910000/91907800/91907749/6738b703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91910000/91907800/91907749/fb075558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/92000000/91910000/91907800/91907749/w1199h675x1y0-839184c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LakeAccess 4BR DeckSlide OD Movies HotTub Kayaks Oakland 10/10 Exceptional (13) "There were 6 of us. We had a great time. House is beautiful. Great location. " [](https://www.expedia.ca/Oakland-Hotels-Redesigned-Cabin.h91907749.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) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115770000/115760100/115760069/fb4d79f0.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) ### Private & Spacious 8-bedroom lodge with amazing outdoor space and game room Oakland CA $1,333 CA $2,379 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Oakland-Hotels-Private-Spacious-8-Bedroom-Lodge-With-Amazing-Outdoor-Space-And-Game-Room.h115760069.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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4150000/4144900/4144866/w3837h2557x3y3-65d16e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave (with Single Sofabed;Larger Room)](https://images.trvl-media.com/lodging/5000000/4150000/4144900/4144866/92c63a63.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) ### SureStay Plus Hotel by Best Western Keyser Keyser 8.8/10 Excellent (529) "Easy registration and friendly service. Free hot breakfast was yummy!" CA $172 CA $193 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Keyser-Hotels-SureStay-Plus-Hotel-By-Best-Western-Keyser.h4144866.Hotel-Information) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1347/d408e68b.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 (696) "Family friendly. Easy access to interstate" CA $149 CA $170 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Cumberland-Hotels-Comfort-Inn-Grantsville.h1347.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=2025-10-29&endDate=2025-10-30®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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