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Oakland vacation rentals

We found 1,524 vacation rentals — enter your dates for availability

Select from 464 houses, 54 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

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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 when booking a vacation rental?
When planning a vacation in Oakland, Maryland, a great area to consider for your stay is the charming downtown area. This vibrant neighborhood boasts a selection of vacation rentals that superbly capture the essence of the town, often characterized by cozy cabins and charming cottages. The downtown area is not only picturesque but also conveniently located near several attractions. One of the top highlights is the beautiful Deep Creek Lake, where visitors can enjoy a variety of outdoor activities such as boating, fishing, and hiking along the scenic trails. Additionally, the nearby Wisp Resort offers year-round fun, with skiing in the winter and mountain biking in the summer, making it an ideal spot for adventure seekers.

Another wonderful option is the area surrounding the Oakland State Park, which provides a tranquil setting for a peaceful retreat. This neighborhood features numerous vacation rentals that offer a serene escape while still being close to nature. The state park is a fantastic place to explore, with hiking trails and opportunities for wildlife viewing. Here, you can unwind in a natural setting while still accessing the local shops and dining options that Oakland has to offer.

Overall, both the downtown area and the Oakland State Park vicinity have a diverse range of properties available for rent, ensuring you can find the superb place to call home during your visit.
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, travelers should consider the scenic areas surrounding Deep Creek Lake. This beautiful destination offers a variety of rental options, particularly along the lakefront, where guests can enjoy stunning views and easy access to water activities. Many properties in this area come equipped with amenities such as private docks, outdoor decks, and fire pits, making them ideal for families or groups looking to enjoy lakeside living.

Additionally, the neighborhoods near the Wisp Resort provide excellent options for those seeking a more active vacation. Rentals here often feature amenities like game rooms, hot tubs, and full kitchens, superb for unwinding after a day of skiing in the winter or hiking and biking in the summer. The proximity to local shops, restaurants, and recreational activities enhances the convenience for travelers.

Furthermore, the surrounding natural beauty of the area, including state parks and trails, offers numerous opportunities for outdoor exploration.
Where are the best Oakland ski resort rentals?
For ski resort rentals near Oakland, Maryland, travelers should focus on the nearby Wisp Resort, which is just a short drive away. In and around Deep Creek Lake, you'll find a variety of accommodations that cater to winter sports enthusiasts. Many properties in this area include cozy chalets and cabin rentals, often featuring amenities such as fireplaces, hot tubs, and spacious decks that overlook the beautiful lake or wooded surroundings.

The area boasts both rustic charm and modern conveniences, with many rentals providing fully equipped kitchens, making it easy for families or groups to prepare meals after a day on the slopes. Some properties also offer access to community amenities like indoor pools and fitness centers, enhancing the overall experience.

In addition to skiing, the Deep Creek Lake area offers opportunities for snowboarding and tubing, as well as winter hiking trails for those looking to explore the picturesque scenery. The local town of Oakland features quaint shops and dining options, providing a superb blend of adventure and relaxation for travelers enjoying their ski getaway.
What is the most popular type of vacation rental accomodation in Oakland?
In Oakland, vacation houses are the most popular type of rental, with around 408 available throughout the area. These houses often provide spacious rooms, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces like decks or patios that allow guests to enjoy the beautiful surroundings. Many are located near Deep Creek Lake, making them ideal for those looking to engage in water activities or relax by the shore.

Cottages are also a favored option, with about 88 available. These charming properties typically offer a cozy atmosphere, complete with essential amenities such as kitchen facilities and comfortable living spaces. They are often found in serene neighborhoods, superb for a peaceful getaway.

Additionally, there are approximately 77 cabins available, which are popular for their rustic charm and proximity to nature. These cabins usually come with fireplaces, outdoor seating, and sometimes hot tubs, providing a superb retreat for those looking to immerse themselves in the natural beauty of the area.

Finally, around 45 condos are available, often located in more developed areas with easy access to local attractions, dining, and shopping. These condos typically feature modern amenities and may include access to community facilities like pools or fitness centers.
Are there any family house rentals in Oakland?
In Oakland, Maryland, there are plenty of family-friendly house rentals available, with around 422 options to choose from. This charming area is known for its beautiful landscapes and outdoor activities, making it an ideal spot for families. Many homes feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces great for children to play. Common amenities include cozy fireplaces, game rooms, and private decks or patios where families can enjoy the fresh mountain air.

Nearby attractions such as Deep Creek Lake offer opportunities for swimming, boating, and fishing, while the surrounding areas are great for hiking and exploring nature. Visitors can also find local shops and restaurants that serve delicious regional cuisine just a short drive away. 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 many vacation homes available for rent that feature pools or hot tubs, with around 175 options to choose from. This picturesque area, located in the beautiful landscapes of Deep Creek Lake, offers a range of properties suitable for various group sizes and budgets. Many of these rentals come with private pools and hot tubs, superb for relaxing after a day of outdoor activities.

Travelers can expect amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces for barbecuing or enjoying the scenic views. 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, Maryland, there are numerous pet-friendly house rentals available, with a total of 194 options for travelers to choose from. These rentals typically offer a variety of amenities, including spacious living areas, fully equipped kitchens, and outdoor spaces like decks or patios where pets can enjoy the fresh air. Many properties also feature cozy fireplaces and modern conveniences such as Wi-Fi and laundry facilities, making them ideal for families and groups traveling with pets.

The area around Oakland is known for its beautiful natural surroundings, including Deep Creek Lake, which offers ample opportunities for outdoor activities such as hiking, fishing, and boating. With close proximity to state parks and scenic trails, these rentals provide a superb base for exploring the great outdoors while accommodating your furry friends. See all pet-friendly rentals in Oakland.
Are there any remote work vacation rentals in Oakland?
In Oakland, Maryland, remote work vacation rentals are plentiful, with around 591 options available for those looking to combine work and leisure. The area is known for its beautiful surroundings, including Deep Creek Lake, which offers a serene backdrop for productivity. Many properties are equipped with essential amenities for remote work, such as Wi-Fi, dedicated office spaces, ergonomic desks, and comfortable chairs, ensuring that guests can work efficiently while enjoying the tranquility of the region.

Additionally, the proximity to recreational activities like hiking, boating, and fishing provides an excellent opportunity to unwind after a day's work. Visitors will find that rentals often include spacious living areas and fully equipped kitchens, making it easy to balance work and relaxation. 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 WiFi, kitchens, and patios, making it easy for travelers to stay connected and prepare their own meals. Many rentals feature fireplaces, adding a cozy touch for chilly evenings, and for those who enjoy golfing, there are options with onsite golf facilities.
When is the best time to visit Oakland for a vacation rental?
July is the most popular time to visit Oakland, Maryland, when the summer season is in full swing. This peak period usually extends from July through September, attracting families and outdoor enthusiasts eager to enjoy the warm weather and an array of recreational activities. With temperatures typically ranging from the mid-70s to the low 80s Fahrenheit, visitors can comfortably explore the picturesque landscapes, whether it's hiking in the nearby state parks, enjoying water sports on Deep Creek Lake, or attending local festivals.

For those who prefer a quieter experience, consider planning your trip in December. While this month is part of the low season, it offers a unique charm with its winter scenery and festive decorations. This time is great for visitors looking to enjoy cozy indoor activities, such as visiting local shops or savoring warm meals at charming restaurants.
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?
In Oakland, Maryland, visitors can enjoy a variety of attractions amidst its beautiful natural setting. The Deep Creek Lake area is a primary draw, offering opportunities for boating, fishing, and swimming. Nearby, Swallow Falls State Park features stunning waterfalls and scenic hiking trails, making it great for outdoor enthusiasts. Vacation rentals in this area often provide easy access to both the lake and the park, allowing guests to fully immerse themselves in nature.

For those interested in local history, the Oakland Museum showcases the town's rich heritage and is located in the heart of the downtown area. The charming Main Street offers quaint shops, local eateries, and seasonal events that highlight the community's vibrant culture. Additionally, Wisp Resort, located just a short drive away, provides year-round recreational activities, including skiing in the winter and mountain biking in the summer, making it a popular choice for adventure seekers.
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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