Photo by Jenn Charbonneau

Oakland vacation rentals

We found 1,536 vacation rentals — enter your dates for availability

Select from 471 houses, 53 condos, and other vacation rentals to find the perfect place for your stay in Oakland. Whether you're traveling with a group or just with your pet, vacation homes have the best amenities for spending time at your vacation home, which might include a garden and WiFi. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Oakland

Showing deals for:May 29 - Jun 5

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Find out more about Oakland

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.4°F (-3.1°C)Light RainMostly CloudyAverageSlightly High
February30.0°F (-1.1°C)Light RainMostly CloudySlightly LowSlightly High
March37.6°F (3.1°C)Light RainMostly CloudyAverageSlightly Low
April47.7°F (8.7°C)Light RainMostly CloudyAverageSlightly Low
May57.6°F (14.2°C)Light RainMostly CloudyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
July69.1°F (20.6°C)Light RainMostly SunnySlightly HighAverage
August67.3°F (19.6°C)Light RainMostly SunnyAverageAverage
September61.5°F (16.4°C)Light RainMostly SunnySlightly HighAverage
October50.7°F (10.4°C)Light RainMostly SunnyAverageSlightly Low
November39.0°F (3.9°C)Light RainMostly SunnySlightly LowAverage
December32.5°F (0.3°C)Light RainMostly CloudySlightly LowSlightly 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.

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your reservation. It truly pays off to take the lead in planning. By joining our travel rewards program, One Key, you can easily access member discounts and earn OneKeyCash on qualifying bookings. Sign up today and begin enjoying the savings.

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.

Frequently asked questions

What is the best area to stay in Oakland, Maryland, United States of America when booking a vacation rental?
When looking for the best area to stay in Oakland, Maryland, you might want to consider the charming neighborhoods near Deep Creek Lake. This beautiful area not only offers stunning lake views but also provides access to a variety of outdoor activities, making it a fantastic destination for nature lovers and adventure seekers alike.

The area around the lake features numerous vacation rentals, ranging from cozy cabins to spacious homes, giving you plenty of options to choose from. One of the top attractions nearby is Deep Creek Lake State Park, where visitors can enjoy hiking, fishing, and boating during the warmer months, while in the winter, the area transforms into a winter wonderland superb for skiing and snowboarding at nearby resorts.

Another highlight in the vicinity is the Wisp Resort, which is well-known for its year-round activities, including golf in the summer and skiing in the winter. Staying in this area not only places you near these exciting attractions but also allows you to experience the natural beauty and tranquility that Oakland has to offer.
How much does it cost to rent a vacation home in Oakland?
Prices for vacation rentals in Oakland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oakland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oakland vacation house rentals?
You can find great discounts on house rentals in Oakland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Oakland?
For renting a beach house in Oakland, Maryland, the area around Deep Creek Lake is a prime choice. This picturesque region offers a variety of vacation rentals with stunning lakefront views and easy access to water activities such as boating, fishing, and swimming. Many properties in this area come equipped with amenities like private docks, outdoor fire pits, and spacious decks, great for enjoying the serene surroundings and breathtaking sunsets.

Travelers can also explore the nearby Wisp Resort, where additional accommodations can be found. These rentals often feature cozy interiors, fireplaces, and access to resort amenities, including skiing in the winter and mountain biking during the warmer months. The surrounding area is rich with recreational opportunities, including hiking trails and local parks, making it ideal for nature enthusiasts.

In addition to outdoor activities, the Oakland area provides access to charming local shops and restaurants, ensuring that visitors have everything they need for a comfortable stay. Find your rental near the beach in Oakland.
Where are the best Oakland ski resort rentals?
For the best ski resort rentals near Oakland, Maryland, travelers should focus on the area around Deep Creek Lake, which is approximately a 30-minute drive away. This region is renowned for its winter sports, particularly at Wisp Resort, where visitors can find a variety of accommodations ranging from cozy cabins to spacious lodges. Many of these properties come equipped with modern amenities such as gas fireplaces, hot tubs, and fully equipped kitchens, making them ideal for families and groups looking to unwind after a day on the slopes.

In the vicinity of Deep Creek Lake, there are charming vacation homes and condos that offer stunning views of the lake and surrounding mountains. These rentals often include outdoor decks, superb for soaking in the scenery, and some even feature game rooms or access to community amenities like pools and fitness centers. The area is also dotted with local shops, restaurants, and recreational activities, providing a well-rounded experience for travelers.

Additionally, the nearby state parks offer opportunities for snowshoeing and cross-country skiing, adding to the winter adventure.
What is the most popular type of vacation rental accomodation in Oakland?
In Oakland, vacation houses are the most popular type of rental, with about 355 available throughout the area. These homes typically feature spacious layouts, full kitchens, multiple bedrooms, and often outdoor spaces like decks or patios, making them ideal for families or larger groups looking to enjoy the natural beauty of the surrounding area. Additionally, there are around 92 cottages that offer a charming, cozy atmosphere, often with rustic decor and proximity to local attractions such as Deep Creek Lake and the surrounding state parks. For those seeking a more rustic experience, approximately 73 cabins are available, providing a quintessential getaway in a wooded setting. Condos, numbering around 47, offer a more modern option, usually equipped with amenities like pools or fitness centers. Finally, there are 13 chalets that provide a unique stay, often featuring scenic views and a blend of comfort and adventure.
Are there any family house rentals in Oakland?
In Oakland, Maryland, there are numerous family-friendly house rentals available, with around 431 options to choose from. This charming area near Deep Creek Lake offers a variety of accommodations that cater well to families. Many of these properties feature spacious living areas, fully equipped kitchens superb for preparing family meals, and outdoor spaces where children can play or where families can have barbecues.

Depending on the location of the rental, visitors may find themselves close to attractions such as the scenic Deep Creek Lake State Park, known for its hiking trails, picnic areas, and water activities. Other nearby points of interest include Wisp Resort, which provides opportunities for year-round outdoor fun, including skiing in the winter and mountain biking in the summer. See all family-friendly rentals in Oakland.
Can I rent a vacation home with a pool or hot tub in Oakland?
In Oakland, Maryland, there are plenty of vacation homes available for rent that feature pools or hot tubs, with around 145 options to choose from. This picturesque area offers a range of properties located near Deep Creek Lake, where travelers can enjoy both relaxation and outdoor activities. Many of these rentals come equipped with inviting private pools, hot tubs, and spacious outdoor decks, superb for entertaining or unwinding after a day of adventure.

The amenities you can expect include fully equipped kitchens, cozy living spaces, and often fireplaces, making these homes ideal for families or groups. Additionally, some properties may offer access to lakefront activities, such as boating and fishing, enhancing the overall experience in this beautiful part of Maryland.
Can I find long-stay vacation rentals in Oakland?
A long-stay vacation rental in Oakland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Oakland?
In Oakland, Maryland, visitors will find a variety of pet-friendly house rentals available, with around 196 options to choose from. Many of these homes are equipped with desirable amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces that often include decks or patios, great for enjoying the scenic surroundings.

The area is known for its proximity to Deep Creek Lake, where travelers can enjoy outdoor activities with their pets, including hiking, fishing, and boating. Additionally, the nearby Swallow Falls State Park offers beautiful trails and stunning waterfalls, making it an excellent spot for outdoor adventures with furry companions.
Are there any remote work vacation rentals in Oakland?
In Oakland, Maryland, there are numerous vacation rentals suitable for remote work, with around 562 options available. The area is known for its beautiful natural scenery, making it an appealing choice for those looking to combine work and leisure. Many properties offer essential amenities such as high-speed Wi-Fi, free internet access in rooms, and public areas, ensuring a productive work environment.

Travelers can expect a variety of accommodations, including cozy cabins and spacious homes, often featuring dedicated workspaces, comfortable seating, and tranquil settings that promote focus. Additionally, the proximity to Deep Creek Lake provides opportunities for outdoor activities during breaks, such as hiking, boating, and enjoying the stunning views. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oakland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oakland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Oakland?
In Oakland, Maryland, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their meals conveniently. Many properties feature cozy fireplaces, superb for warming up after a day of outdoor activities. Hot tubs are also a sought-after amenity, providing a relaxing way to unwind in the evenings. Onsite parking is available at most rentals, making it easy for guests to come and go without hassle. Additionally, many rentals come equipped with coffee and tea makers, ensuring that travelers can enjoy their morning beverage of choice in the comfort of their accommodations.
When is the best time to visit Oakland for a vacation rental?
The peak season for visiting Oakland, Maryland, is from July to September, when the area comes alive with vibrant summer activities. This is a wonderful time for travelers who enjoy outdoor adventures, as visitors can partake in hiking, boating, and fishing in the picturesque landscapes surrounding Deep Creek Lake. The warm temperatures, typically ranging from the mid-70s to mid-80s Fahrenheit, create great conditions for enjoying everything from scenic picnics to lively local festivals.

July stands out as the most popular month for vacation rentals in Oakland. During this time, families and adventure seekers flock to the area to relish the natural beauty and join in on community events. You can immerse yourself in the lively option, with plenty of opportunities for water sports and exploring the stunning state parks nearby.

For those considering a more budget-friendly option, October is an excellent time to visit Oakland. The crowds taper off, allowing for a peaceful experience amidst the breathtaking fall foliage. You can enjoy scenic drives along the lake or hiking trails where the autumn colors create a stunning visual display.

Ultimately, the best time to book your vacation rental in Oakland depends on your preference for vibrant summer activities or the tranquil beauty of autumn.
How early should I book a Oakland vacation rental?
Book your Oakland vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oakland, Maryland, United States of America?
In Oakland, Maryland, visitors can enjoy a variety of attractions centered around its stunning natural beauty and outdoor activities. The area is known for Deep Creek Lake, where travelers can partake in boating, fishing, and swimming during the warmer months. Lake State Park, situated nearby, offers hiking trails, picnic areas, and opportunities for wildlife viewing, making it a great spot for nature enthusiasts.

The town also features unique shops and restaurants along the main street, providing a local flavor and a chance to explore regional cuisine. For those interested in winter sports, the Wisp Resort, located a short drive away, offers skiing and snowboarding during the colder months.
Can I change or cancel my Oakland home rental booking on Vrbo?
To find Oakland vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oakland vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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