Oakland vacation rentals

We found 203 vacation rentals — enter your dates for availability

Welcome to Oakland, where serene landscapes and breathtaking lakes create an idyllic backdrop for your next getaway. This charming destination invites outdoor enthusiasts to paddle board, hike, and unwind in nature’s embrace, while cozy cabins and cottages provide the perfect home-like sanctuary for groups and families. With local attractions like the historic Waterville Opera House and the picturesque Belgrade Lakes Chain just a stone's throw away, staying in a vacation rental enhances your experience with comfort, space, and the freedom to explore at your leisure.

Holiday rentals with weekly discounts - Oakland

Showing deals for:Nov 13 - Nov 20

Living room towards dining room
Camp at night
Bar and grill on porch
Cozy seat hammocks on the porch - amazing views!
Exceptional
(56 reviews)

Maine Cabin on the Water

Belgrade

9% off
$321
$2,244 for 7 nights
All fees included
Maine Cabin on the Water
Property grounds
Property grounds
Private kitchen
Living area
Exceptional
(9 reviews)

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Oakland

9% off
$512
$3,585 for 7 nights
All fees included
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Dining
Outdoor spa tub
Game room
Exterior
Exceptional
(7 reviews)

Lake Great Pond, Outdoor Hot Tub, Sauna, Pool Table

Belgrade

38% off
$700
$4,900 for 7 nights
All fees included
Lake Great Pond, Outdoor Hot Tub, Sauna, Pool Table
Room
Exterior
Living area
Exceptional
(16 reviews)

BELGRADE LAKES MAINE GREAT POND PRIVATE 2-BEDROOM COTTAGE 15 FEET FROM WATER

Belgrade

8% off
$237
$1,661 for 7 nights
All fees included
BELGRADE LAKES MAINE GREAT POND PRIVATE 2-BEDROOM COTTAGE 15 FEET FROM WATER
front door looks off to the woods
open living space with views of the Northwest mountains.
Springtime view
Exterior
Exceptional
(30 reviews)

A soul soothing escape. Artistically built and lovingly maintained.

New Sharon

8% off
$288
$2,016 for 7 nights
All fees included
A soul soothing escape. Artistically built and lovingly maintained.
Interior
Interior
Interior
Private kitchen
Exceptional
(15 reviews)

Mercer Apartment in the Valley-Peaceful Country!

Norridgewock

8% off
$177
$1,238 for 7 nights
All fees included
Mercer Apartment in the Valley-Peaceful Country!
Property grounds
Living area
Bedroom #2 queen size
Andrea's Cozy House
Exceptional
(60 reviews)

Cozy House in the heart of Waterville Maine.

Waterville

8% off
$163
$1,141 for 7 nights
All fees included
Cozy House in the heart of Waterville Maine.

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Find out more about Oakland

Why visit Oakland

  • Outdoor adventures: Oakland offers access to beautiful lakes and nearby state parks, perfect for recreation and family outings.
  • Charming accommodations: Choose from cozy cottages and rustic cabins for a romantic retreat or peaceful getaway.
  • Cultural experiences: Explore historic colleges and universities that enrich the local atmosphere.
  • Scenic views: Enjoy the stunning natural beauty that surrounds Oakland, ideal for nature lovers.
  • Welcoming atmosphere: Oakland provides a friendly environment for families, couples, and solo travelers alike.

Popular types of accommodation in Oakland

Explore the diverse vacation rental options in Oakland, ME, where you'll find charming houses, cozy cottages, and rustic cabins. Whether you're seeking a peaceful retreat or a base for adventure, our range of house rentals in Oakland caters to every traveler. Discover the perfect spot for your getaway and enjoy the savings and reassurance that come with booking through our customer-centric platform.

  • Houses: The top choice for visitors in Oakland, these homes offer spacious accommodations perfect for families or groups looking for comfort and privacy.
  • Cottages: A charming option, cottages provide a cozy and quaint atmosphere, ideal for a peaceful getaway in nature.
  • Cabins: These rustic retreats are popular for travelers seeking a true outdoor experience amidst the scenic beauty of Oakland.
  • Apartments: Conveniently located and stylish, apartments are great for those who prefer a more urban feel during their stay.
  • Chalets: These unique lodgings combine comfort with a touch of alpine charm, perfect for a mountain-inspired escape.**

Top attractions near Oakland

Oakland, Maine, is an ideal destination for outdoor enthusiasts and those seeking romantic getaways. Visitors can explore historic colleges and universities, beautiful lakes, and various event venues. The area offers a rich blend of cultural experiences and scenic views, perfect for anyone looking to immerse themselves in nature or enjoy a vibrant city atmosphere. Whether you're traveling solo, with family, or as a couple, Oakland has something special for everyone.

  • Colby College: A historic institution located 3 miles from Oakland, Colby College offers a rich cultural atmosphere with its stunning architecture and beautiful campus. Visitors can enjoy art exhibits and various cultural events throughout the year.
  • Kennebec River: Situated 5 miles away, the Kennebec River boasts breathtaking scenery and outdoor activities. Perfect for kayaking, fishing, or simply enjoying a leisurely walk along its banks, it’s a nature lover's paradise.
  • Waterville Opera House: Located 5 miles from Oakland, this vibrant venue is known for its rich cultural offerings, including live performances and events. It’s a romantic spot for a night out, blending city charm with entertainment.

Things to do recommended for couples

For a romantic getaway in Oakland, explore the scenic Quarry Road Trails for skiing adventures or hit the slopes at Eaton Mountain. In the evening, unwind at Tree Spirits winery, where you can enjoy the intimate atmosphere and delightful local wines for a perfect couple's experience.

Things to do recommended for families

Families can have a blast at the Kennebec Ice Arena, located 17 miles from Oakland. With its lively atmosphere, this ice skating venue offers a perfect blend of sports and entertainment for all ages, ensuring a memorable family outing.

Things to do recommended for groups

Groups visiting Oakland can enjoy a round of golf at Belgrade Lakes Golf, explore the scenic Kennebec River Rail Trail for an adventurous hike, and shop for souvenirs at the Turnpike Mall, perfect for family entertainment and city vibes.

*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 a group, family, pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oakland with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Oakland with young kids: Traveling with young kids can be quite a task. It’s important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oakland: For many families, a vacation isn't truly enjoyable without their furry companion. If you relate to this, take a look at Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oakland: If you're in search of vacation rentals offering discounts for month-long stays, 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 options like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Oakland

Oakland, Maine, offers a delightful mix of outdoor adventures and cozy getaways. Visitors can enjoy scenic lake access, charming vacation homes, and quaint cottages perfect for a romantic retreat. Explore nearby state parks for recreation and family-friendly excursions, all while soaking in the area's rich historical ambiance. Whether you’re seeking relaxation or adventure, Oakland provides a welcoming atmosphere for an unforgettable Maine getaway.

  • Waterville: Situated a mere 5 miles from Oakland, Waterville is a vibrant city that beckons adventurers and nature lovers alike. Known for its stunning outdoor scenery and diverse recreational opportunities, visitors can explore the local hiking trails or hit the slopes at nearby ski fields. The city also boasts educational landmarks, including a historic college university. Don’t miss the chance to enjoy the tranquil beauty of the local lake and the expansive national state park that promises a perfect backdrop for your outdoor escapades.
  • Belgrade Lakes: Just 7 miles away from Oakland, Belgrade Lakes is a charming city renowned for its romantic ambiance and picturesque landscapes. This destination is ideal for those seeking outdoor activities, featuring excellent ski fields and pristine golf courses. The area is famous for its stunning lakes and inviting beaches, making it a perfect spot for leisurely afternoons by the water. Whether you're looking for adventure or a tranquil retreat, Belgrade Lakes offers a blend of both in a breathtaking natural setting.
  • Rome: Nestled within the Oakland area, Rome is a quaint village that captivates visitors with its outdoor beauty and serene surroundings. Travelers are drawn to Rome for its romantic atmosphere, featuring recreational areas perfect for picnics or leisurely strolls. Explore the scenic lakes and enjoy the stunning beaches that offer a peaceful escape from the hustle and bustle. With its charming water features and educational opportunities, Rome is a delightful stop for those looking to connect with nature and unwind.

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 from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.9°F (-6.7°C)Light RainMostly CloudyModerately LowSlightly Low
February21.6°F (-5.8°C)Light RainMostly CloudyAverageAverage
March29.8°F (-1.2°C)Light RainMostly CloudyAverageSlightly Low
April42.1°F (5.6°C)Light RainMostly CloudyAverageSlightly Low
May54.0°F (12.2°C)Light RainMostly SunnyAverageSlightly High
June61.9°F (16.6°C)Light RainMostly SunnyModerately HighAverage
July68.9°F (20.5°C)Light RainMostly SunnyModerately HighSlightly High
August67.6°F (19.8°C)Light RainMostly SunnyModerately HighSlightly High
September60.6°F (15.9°C)Light RainMostly SunnyAverageAverage
October49.3°F (9.6°C)Light RainMostly SunnyAverageAverage
November36.7°F (2.6°C)Light RainMostly SunnyModerately LowAverage
December27.3°F (-2.6°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that meets your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up right where you left off, and manage your travel arrangements. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Oakland getaway

Enjoy the monuments and other features of Oakland. This city is well-known for its shopping and restaurants. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Oakland

Are you hoping to discover top things to see and do in the area? Venture out of your cozy vacation rental and check out everything that makes Oakland a fun spot to vacation. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Belgrade Lakes Golf (8.1 mi / 13 km)
  • Natanis Golf Course (8.8 mi / 14.2 km)
  • Augusta Country Club (16.9 mi / 27.2 km)
  • Titcomb Mountain Ski Area (23.2 mi / 37.4 km)
  • Spruce Mountain Jay (24.2 mi / 39 km)
  • Wilson Lake Country Club (26.3 mi / 42.3 km)

Exploring the natural features in Oakland

Whether you're looking for adventure or just want to appreciate the scenery, Oakland is a great place to get out in nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Kennebec River (4.8 mi / 7.7 km)
  • Belgrade Lakes Chain (5.9 mi / 9.6 km)
  • China Lake (10.7 mi / 17.2 km)
  • Echo Lake (16.2 mi / 26.1 km)
  • Capitol Park (16.4 mi / 26.4 km)
  • Maranacook Lake (17.8 mi / 28.7 km)

How to get to and around Oakland

Fly into Waterville, ME (WVL-Robert Lafleur), the closest airport, located 2.1 mi (3.4 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Augusta, ME (AUG-Augusta State), which is 15.8 mi (25.4 km) away.

Frequently asked questions

What is the best area to stay in Oakland, Maine, United States of America when booking a vacation rental?
When considering a vacation rental in Oakland, Maine, the best area to stay is around the scenic waterfront neighborhoods. This region offers a charming atmosphere and easy access to beautiful views of the Kennebec River. You'll find a variety of properties available, from cozy cottages to larger homes ideal for families or groups.One of the top attractions nearby is the Oakland Community Park, a lovely spot for outdoor activities, picnicking, and enjoying nature. Additionally, the area is close to the Belgrade Lakes region, which is renowned for its stunning landscapes and recreational opportunities, such as boating, fishing, and hiking.
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, Maine, travelers should focus on the beautiful waterfront areas along the eastern shore of the town, particularly near the scenic Oakland Beach. This area offers a variety of vacation rentals with direct access to the sandy shores and picturesque views of the lake. Many of the properties in this vicinity come equipped with amenities such as private docks, outdoor decks, and spacious backyards, superb for families or groups seeking a relaxing beach getaway.Additionally, the neighborhood surrounding the nearby Messalonskee Lake provides options for those looking to enjoy water activities like swimming, kayaking, and fishing. Rentals here often feature modern kitchens, air conditioning, and cozy living areas, making them suitable for extended stays.For a more rustic experience, consider the properties located near local parks, which often include amenities like fire pits and picnic areas, allowing guests to enjoy the natural beauty of the region.
Where are the best Oakland ski resort rentals?
For the best ski resort rentals near Oakland, Maine, travelers should focus on the nearby area of Sugarloaf Mountain, which is one of the premier ski destinations in the region. The town of Carrabassett Valley, located just a short drive from Oakland, offers a variety of vacation rentals that cater to ski enthusiasts. Here, visitors can find cozy cabins and lodges that often feature amenities such as hot tubs, fireplaces, and ski-in/ski-out access, making it easy to hit the slopes right from your front door.In Carrabassett Valley, many properties also provide fully equipped kitchens, allowing guests to prepare meals after a long day of skiing. Additionally, some rentals come with communal amenities like game rooms and outdoor fire pits, superb for socializing with friends and family.For those seeking a more local experience, the surrounding area features charming inns and lodges that highlight Maine's rustic charm. These accommodations may offer easy access to local dining options and shops, enhancing the overall experience. Furthermore, the scenic landscapes of the area provide ample opportunity for outdoor activities beyond skiing, such as snowshoeing and snowmobiling, making it an excellent choice for winter sports enthusiasts.
What is the most popular type of vacation rental accomodation in Oakland?
In Oakland, vacation houses are the most popular type of accommodation, with about 26 available throughout the area. These houses typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking comfort and convenience. Additionally, around 15 cabins can be found, offering a rustic charm and proximity to nature, often featuring outdoor spaces for relaxation and gatherings. There are also approximately 11 cottages, which provide a quaint and cozy atmosphere, great for couples or small families. While several apartments are available, they represent a smaller portion of the rental market.
Are there any family house rentals in Oakland?
In Oakland, Maine, there are numerous family-friendly house rentals available—specifically around 48 options to choose from. The town is known for its beautiful lakes and outdoor recreation opportunities, making it a wonderful destination for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or enjoy a barbecue.Travelers can enjoy easy access to nearby attractions such as the scenic Messalonskee Lake, which offers activities like swimming, fishing, and kayaking. The local parks also provide playgrounds and picnic spots, great for family outings. See all family-friendly rentals in Oakland.
Can I rent a vacation home with a pool or hot tub in Oakland?
In Oakland, Maine, there are several vacation homes available for rent that feature pools and hot tubs. This picturesque town offers a serene setting, great for those looking to unwind. Many of the properties come equipped with private pools, hot tubs, and outdoor spaces ideal for relaxation, such as patios or decks where guests can enjoy the beautiful surroundings. Additionally, travelers can expect amenities like fully equipped kitchens and cozy living areas, making these rentals suitable for families or groups. Find your rental in Oakland with a pool or a hot tub.
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, Maine, there are several pet-friendly house rentals available, providing a welcoming environment for travelers with furry companions. Many of these vacation homes are situated near beautiful lakes and nature trails, making it easy for pet owners to enjoy outdoor activities with their pets.Rentals in this area typically feature amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, great for relaxing after a day of exploring. Some properties may even offer additional features like fire pits, outdoor seating areas, and proximity to local parks, enhancing the overall experience for both humans and pets.
Are there any remote work vacation rentals in Oakland?
In Oakland, Maine, there are numerous vacation rentals suitable for remote work, with around 57 options available. These properties typically offer essential amenities such as free Wi-Fi and comfortable workspaces, ensuring that guests can stay productive during their stay. Many of the rentals feature cozy living rooms or dedicated office areas, allowing for a conducive work environment while also providing a cozy feel.The area is known for its scenic beauty, with access to local lakes and parks, making it an appealing option for those looking to balance work and leisure. Travelers can enjoy the peaceful surroundings and explore outdoor activities during their downtime. 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, Maine, popular vacation rental amenities include fully equipped kitchens, superb for travelers looking to prepare their own meals. Many rentals also feature outdoor decks or patios, providing a lovely space to relax and enjoy the natural surroundings. Onsite parking is commonly available, making it convenient for those traveling with vehicles. Additionally, rentals often include coffee and tea makers, allowing guests to enjoy their morning brew at their leisure, along with dining areas where families or groups can gather for meals.
When is the best time to visit Oakland for a vacation rental?
The most popular time to visit Oakland is during the summer months, particularly in July, when the vibrant energy of the region is at its peak. From June to August, travelers flock to Oakland to enjoy warm weather and a variety of outdoor activities, making it an ideal time for those looking to immerse themselves in the local culture and natural beauty.During the summer, temperatures typically range from the mid-60s to the low 80s Fahrenheit, creating great conditions for exploring the picturesque lakes, hiking trails, and charming downtown area. Visitors can take advantage of the numerous recreational opportunities, whether it's kayaking on the serene waters, biking along scenic paths, or attending local festivals that showcase the best of Oakland.If you're seeking a more budget-friendly option, consider planning your visit in December. This month, while quieter, offers a unique charm with festive decorations and a cozy atmosphere. It's a great time to enjoy peaceful walks through the winter landscape and perhaps indulge in some local holiday events.Ultimately, the best time to book a vacation rental in Oakland depends on your preferences for activity level and atmosphere.
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, Maine, United States of America?
In Oakland, Maine, visitors can enjoy a range of attractions that highlight the area's natural beauty and local charm. The scenic Messalonskee Lake is a popular spot for outdoor activities such as kayaking, fishing, and swimming, with several parks and beaches lining its shores. Nearby, the Kennebec Messalonskee Trails offer opportunities for hiking and biking, providing a chance to explore the picturesque landscapes.The town also features the historic downtown area, where travelers can discover quaint shops and local eateries that reflect the community's character. For those interested in local history, the Oakland Historical Society offers insights into the region's past.
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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