Oakland vacation rentals

Why visit Oakland

• Outdoor Adventures: Oakland is a paradise for nature lovers, offering stunning lakes and beautiful state parks for hiking, fishing, and boating.
• Scenic Beauty: The breathtaking scenery of the serene valley provides a perfect backdrop for relaxation and romantic getaways.
• Charming Neighborhoods: Explore vibrant neighborhoods that blend luxury and ecotourism, showcasing local culture and charm.
• Seasonal Attractions: Experience unique seasonal destinations that cater to various interests year-round, making each visit special.
• Diverse Accommodations: Enjoy a range of lodging options, from cozy cabins to modern condos, ensuring a comfortable stay.

Popular types of accommodation in Oakland

If you're exploring vacation rentals in Oakland, you're in luck. Our most popular accommodations include Houses, cozy Cabins, and modern Condos. Whether you're looking for spacious house rentals, essential amenities for a convenient stay, or options for an extended visit, you'll find something that suits your needs. Discover the perfect MD houses for rent and enjoy a memorable getaway in this vibrant city.

• Houses: The top choice for travelers in Oakland, offering spacious and comfortable stays ideal for families or groups.
• Cabins: A popular option for those seeking a rustic experience, these cozy retreats blend nature with comfort.
• Condos: Conveniently located, these rentals provide a modern atmosphere with amenities for a relaxed vacation.
• Chalets: Charming and often set in scenic areas, chalets offer a unique stay with alpine-inspired decor.
• Cottages: Perfect for a quaint getaway, these small homes provide a homey feel and are close to local attractions.**

Top attractions in and around Oakland

Oakland, Maryland, is a perfect destination for outdoor enthusiasts and those seeking a romantic getaway. With stunning lakes, beautiful state parks, and serene nature reserves, you'll find plenty of attractions to explore. Whether you're traveling with family or looking for an adventure, Oakland offers a variety of experiences that cater to all types of travelers. Don’t miss out on the breathtaking scenery and outdoor activities that make this area a must-visit.

• Deep Creek Lake: A picturesque destination perfect for relaxation and romance, Deep Creek Lake offers stunning beaches and scenic views. Enjoy outdoor activities such as boating, swimming, and fishing while soaking in the natural beauty of the area, just 9 miles from Oakland.
• Herrington Manor State Park: Nestled within Oakland, this state park is an outdoor adventure haven. Explore its scenic trails, enjoy hiking, and immerse yourself in nature’s beauty, making it ideal for outdoor enthusiasts.
• Thousand Acres Lakeside Golf Course: Located 9 miles from Oakland, this family-friendly golf course features beautiful lakeside views and well-maintained greens, perfect for a relaxing day of golfing with loved ones.

Things to do recommended for couples

Enjoy a romantic getaway in Oakland, Maryland. Hit the slopes at Wisp Resort for thrilling skiing or embrace adventure at the Adventure Sports Center International with exciting water activities. Both experiences promise unforgettable moments surrounded by stunning outdoor scenery.

Things to do recommended for families

Your family will love exploring the natural beauty of Swallow Falls State Park, where relaxation awaits. For more excitement, head to Funland, an arcade adventure zone just 11 miles away, perfect for family fun and thrilling activities.

Things to do recommended for groups

Experience the great outdoors in Oakland, Maryland, with a round of golf at Lodestone Golf Club or Oakland Golf Course. For adventure seekers, hike the scenic Allegheny Trail, located 14 miles away, and soak in the beautiful landscapes with your group.

What do I need to keep in mind when booking a vacation in Oakland

If you’re planning a trip with friends, family, pets, or looking for extended stays, be sure to prioritize your filters accordingly. Here are some helpful tips for booking on Vrbo.

• Traveling to Oakland with a group: Think about how many bedrooms you’ll require, as well as any amenities like a full kitchen or outdoor area for group get-togethers. Luckily, you can easily filter for all of these options and more on Vrbo.
• Traveling to Oakland with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you are to attractions that are enjoyable for families.
• Taking your pets with you to Oakland: For many families, a trip isn’t truly fulfilling without their furry companions. If that describes you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Oakland: If you're searching for vacation rentals that offer discounts for extended stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Oakland

Oakland, Maryland, offers a delightful mix of outdoor adventures and stunning scenery, perfect for a romantic getaway or family vacation. Explore the vibrant city and its charming neighborhoods, where luxury meets ecotourism. Enjoy the serene atmosphere of the scenic valley, ideal for relaxation and seclusion. Oakland’s seasonal destinations provide unique experiences year-round, making it a must-visit for travelers seeking both tranquility and trendy vibes.

• Thayerville: Nestled within the beautiful landscapes of Oakland, Thayerville is a quaint village that offers a perfect blend of outdoor adventure and serenity. Visitors are drawn to its picturesque scenery, making it an ideal spot for romantic getaways. The area boasts a range of recreational activities, including skiing and access to ski resorts. Nature lovers will appreciate the nearby national parks and lakes, providing ample opportunities for hiking, fishing, and enjoying stunning views. Thayerville's charm and proximity to natural attractions make it a must-visit for those seeking relaxation and adventure.
• Alpine Lake: Located approximately 7 miles from Oakland, Alpine Lake is a hidden gem that attracts travelers looking for outdoor experiences and breathtaking scenery. This village is perfect for couples seeking a romantic retreat, with its tranquil lake and surrounding parks. Popular activities include skiing and enjoying recreational areas, making it a great destination regardless of the season. The nearby national state park enhances the allure, offering hiking trails and opportunities to immerse yourself in nature's beauty. Alpine Lake is truly a picturesque escape for outdoor enthusiasts and lovers of serene landscapes.
• Swanton: About 10 miles from Oakland, Swanton is a vibrant city that offers a wealth of outdoor activities and stunning scenery. Known for its romantic ambiance, Swanton invites visitors to explore its recreational areas and ski resorts. The proximity to lakes and rivers provides a perfect backdrop for fishing, boating, and hiking adventures. With its stunning natural beauty and easy access to national parks, Swanton is an excellent choice for travelers seeking both relaxation and outdoor excitement. This charming city is sure to provide memorable experiences for everyone.

Best time to go to Oakland

If you're planning a trip to Oakland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	26.4°F (-3.1°C)	Light Rain	Mostly Cloudy	Average	Slightly High
February	30.0°F (-1.1°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly High
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	Average
August	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Average
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

Booking with Vrbo is simple

Are you aiming to save on your upcoming journey? Being open to adjusting your travel dates can really help, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for planning new trips, managing your existing travel plans, or reviewing and organizing your bookings. Your saved or reserved properties are categorized into Potential, Upcoming, or Current Trips for easy access. To discover all the features of Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

A gateway to untamed Maryland

Surrounded by towering forests and shimmering lakes, Oakland is a laid-back town in the heart of Garrett County. A true all-season destination, it lures sunseekers, snow bunnies and leaf peepers alike. Whether you want to whitewater raft down the Youghiogheny River, hit the slopes at Wisp Resort or simply relax on the deck of your Oakland vacation rentals hideaway, it's an enchanting slice of Maryland. You'll also be an easy hop from Deep Creek Lake, a year-round outdoor playground offering swimming, fishing, boating, hiking and more.

Discover Oakland's flourishing arts scene

With its scenic setting and free-spirited lifestyle, Oakland is a hotspot for artists. Check out local talent at the Spruce Forest Artisan Village, where you can wander around historic workshops and chat to resident artists. The Simon Pearce Glassblowing Workshop is another highlight, treating visitors to demonstrations, workshops and a colorful gift store. While nearby Broadford Lake is a favorite with locals, Deep Creek Lake steals the spotlight. It serves up endless family fun, from kayaking and sailing to jet skiing and speed boating.

Leaf peeping in Oakland

Every fall, Oakland explodes in a sea of reds, yellows and golds. In fact, it's regularly named one of the best places in America to admire fall foliage. The town celebrates with the annual Autumn Glory Festival, a 5-day celebration filled with music, art, parades, street stalls and, of course, fiery fall colors. Summer is also a busy time, especially over the US school holidays. Planning a family vacation? With plenty of pet-friendly Oakland vacation rentals to choose from, whisking the whole family to Maryland has never been easier.

Reel in monster-sized trout

Set in Garrett County, Oakland is tucked away in a scenic valley. It's surrounded by white pines, hemlocks, maples, hickories and, of course, plenty of oaks. The town is just 10 miles from Deep Creek Lake, one of Maryland's most visited summer destinations. The Youghiogheny River carves through the landscape and is brimming with monster-sized trout. From family-friendly walks to backcountry hikes, Garrett County is surrounded by national parks and state forests. You can mountain bike in Swallow Falls State Park, hike through heritage-listed oak groves in Garrett State Forest or relax by the lake in Broadford Park.

Transportation to and around Oakland

The nearest airport is in Morgantown, WV (MGW-Morgantown Municipal), located 31.8 mi (51.2 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Elkins, WV (EKN-Randolph County), which is 43.3 mi (69.7 km) away.