Oakland Vacations from $719

Things to do in and around Oakland

Oakland, Maryland, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore the scenic beauty of the area, enjoy various outdoor adventures, and take advantage of recreational activities. Popular attractions include local ski resorts and vibrant nightlife options, ensuring there’s something for everyone to enjoy during their stay in this charming town.

Shopping

In Oakland, you can visit local shops like the Oakland Antique Mall for unique finds and handmade crafts. If you're up for a drive, head to the nearby Deep Creek Lake area, where you'll find the Wisp Resort's shops and local boutiques offering a variety of gifts and souvenirs.

Recreation

Explore Swallow Falls State Park for serene hikes among breathtaking waterfalls and lush forests, perfect for relaxation and rejuvenation. Enjoy a round at Lodestone Golf Club, where stunning mountain views meet challenging greens, blending sports with the great outdoors. Experience the cultural charm at Music at Penn Alps, featuring live performances in a cozy theater setting.

Adventure

Experience the thrill of skiing at Wisp Resort, located 11 miles from Oakland, where you can carve through snowy slopes. For water adventures, head to Adventure Sports Center International, 10 miles away, for exciting water sports. Enjoy family-friendly fun at Funland, also 11 miles from Oakland, with arcade games galore.

Nightlife

Oakland's nightlife offers a cozy atmosphere with local bars and live music. Check out the MoonShadow Café for great food and entertainment. For a laid-back vibe, visit the Deep Creek Brewing Company, where you can enjoy craft beers and often catch live performances from talented musicians.

Find the best attractions near Oakland

Oakland, Maryland, is perfect for outdoor enthusiasts and those seeking a romantic getaway. Visitors can explore beautiful lakes, national parks, and nature reserves, making it ideal for family adventures. Don’t miss local attractions like the Oakland Zoo, Oakland Museum, and Oakland Arena for an engaging experience in this charming town.

• Deep Creek Lake: Experience the serene beauty of Deep Creek Lake, a stunning destination perfect for beach outings and romantic sunsets. The lake offers a variety of outdoor activities, from swimming and fishing to kayaking, all set against picturesque scenery that invites relaxation and adventure.
• Cathedral State Park: Immerse yourself in the natural wonders of Cathedral State Park, where adventure awaits amidst towering trees and scenic trails. Ideal for hiking and exploring, this park offers a peaceful retreat with opportunities to connect with nature in a breathtaking outdoor setting.
• Thousand Acres Lakeside Golf Course: Enjoy family-friendly fun at Thousand Acres Lakeside Golf Course, where golf enthusiasts of all ages can play on a beautifully maintained course. The welcoming atmosphere and stunning lakeside views make it a perfect spot for a day of recreation and quality family time.

Best time to go to Oakland

The best time to visit Oakland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	26.4°F (-3.1°C)	Light Rain	Mostly Cloudy	Average	Average
February	30.0°F (-1.1°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
March	37.6°F (3.1°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	47.7°F (8.7°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	57.6°F (14.2°C)	Light Rain	Mostly Cloudy	Average	Average
June	64.9°F (18.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	69.1°F (20.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	61.5°F (16.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	50.7°F (10.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
November	39.0°F (3.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	32.5°F (0.3°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly High

Tips to save on your trip to Oakland

• Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Oakland.
• Consider traveling to Oakland during the low season (March to April and October) for more affordable options.
• Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
• Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.