Olean vacation rentals

We found 34 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Olean to find one that's perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the amenities you expect for your stay, which might include WiFi and a fireplace. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including accessible or non-smoking choices.

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Find out more about Olean

Why visit Olean

  • Outdoor Adventures: Olean is a haven for outdoor enthusiasts, offering scenic parks and breathtaking overlooks for hiking and exploring.
  • Charming Towns: Visit nearby Allegany and Portville, known for their family-friendly atmosphere and delightful local vibes.
  • Military Museums: Discover history at local military museums that showcase Olean's rich heritage and military significance.
  • Vacation Rentals: Choose from a variety of cozy accommodations, including charming cabins and private vacation homes.
  • International Culture: Take a short trip to Ontario, Canada, for a taste of international flair and culture.

Popular types of accommodation in Olean

Discover the charm of Olean with a variety of vacation rentals tailored to your needs. From cozy houses and inviting chalets to rustic cabins, there's something for everyone. Whether you're searching for apartment rentals, friendly house rentals, or homes equipped with Wi-Fi, Olean has you covered. Choose the perfect accommodation for a memorable stay and enjoy the beauty of this delightful destination.

  • Houses: The top choice for visitors in Olean, these homes offer spacious and comfortable accommodations for families or groups.
  • Chalets: A charming option, chalets provide a cozy atmosphere and often feature beautiful views, ideal for a relaxing getaway.
  • Cabins: Perfect for nature lovers, cabins offer a rustic experience, often nestled in serene surroundings.
  • Cottages: Quaint and inviting, cottages are great for couples or small families seeking a peaceful retreat.
  • Condos: With modern amenities, condos provide convenience and comfort, making them a popular choice for travelers.**

Top attractions near Olean

Olean, New York, is perfect for outdoor enthusiasts and adventure seekers, offering a variety of scenic experiences. Explore popular attractions such as urban parks, military museums, and private country clubs. Whether you're traveling with family or friends, Olean provides an ideal blend of urban and outdoor activities to enjoy during your visit. Don't miss the chance to immerse yourself in the beauty and charm of this delightful city.

  • Rock City Park: Located 5 miles from Olean, this urban park offers stunning rock formations and scenic trails perfect for family outings. Enjoy outdoor activities amidst nature's beauty, making it an ideal spot for picnics and exploration.
  • Eldred World War II Museum: Situated 9 miles away, this military museum provides a deep dive into WWII history with engaging exhibits and artifacts. It's a cultural gem that honors the sacrifices of veterans, making it a meaningful visit.
  • Birch Run Country Club: Just 5 miles from Olean, this private country club exudes luxury. Enjoy pristine golf courses and elegant facilities, perfect for a relaxing day of leisure and fine dining.

Things to do recommended for couples

For a romantic getaway in Olean, head to Birch Run Country Club, just 5 miles away. Enjoy the luxurious atmosphere while playing a round of golf or savoring a meal together. It's the perfect spot for couples looking to unwind and connect amidst beautiful scenery.

Things to do recommended for families

Families visiting Olean can enjoy a fun-filled day at the Good Times of Olean, an amusement center featuring arcade games and mini-golf. Additionally, the Olean Public Library offers engaging storytimes and activities for children, making it a great spot for family bonding.

Things to do recommended for groups

Explore the scenic beauty of Allegany State Park with hiking and picnicking, or visit the historic Olean General Hospital to learn about local history. For a fun evening, check out local breweries for craft beer tastings and enjoy live music at nearby venues.

*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 Olean

If you're traveling with a group, family, or pets, or if you're planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Olean with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Olean with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions for a more enjoyable experience.
  • Taking your pets with you to Olean: For many families, a vacation wouldn’t be the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Olean: If you're in search of vacation rentals offering discounts for 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 rental options. 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 Olean

Olean, New York, offers a delightful blend of adventure and scenic beauty, making it a perfect destination for outdoor enthusiasts. Explore the charming towns of Allegany and Portville, where family-friendly vibes abound. Don’t miss the stunning overlooks that provide breathtaking views, and consider a short trip to Ontario, Canada, for a touch of international culture. With warm town hospitality, Olean promises an unforgettable getaway filled with historical charm and natural wonders.

  • Allegany: Nestled just 3 miles from Olean, Allegany is a charming city that beckons outdoor enthusiasts and adventure seekers alike. Surrounded by picturesque scenery, Allegany offers a plethora of recreational opportunities, including skiing at nearby resorts and exploring the vast national state park. Visitors can immerse themselves in nature, whether it's by hiking trails or enjoying the serene beauty of the local lakes. With events held at its conference venues, Allegany balances adventure and community spirit, making it a perfect getaway for those looking to connect with nature and participate in local activities.
  • Saint Bonaventure: A mere 3 miles from Olean, Saint Bonaventure is a vibrant city known for its rich cultural themes and beautiful landscapes. The city is home to an esteemed university, attracting visitors interested in education and history. Golf enthusiasts can enjoy local courses, while recreational areas provide opportunities for outdoor relaxation and fun. The stunning lakes and the nearby national state park further enhance Saint Bonaventure's appeal, allowing tourists to enjoy both cultural and natural attractions in a single visit.
  • Westons Mills: Located within the Olean area, Westons Mills is a quaint village that offers a romantic and scenic atmosphere. Visitors are drawn to its charming parks and historic sites, making it a great spot for leisurely strolls and exploration. The village features a shopping center for those looking to indulge in retail therapy, while recreational areas provide ample opportunities for outdoor activities. With its picturesque lakes and welcoming community, Westons Mills is perfect for couples and families seeking a peaceful retreat close to nature.

Best time to go to Olean

If you're planning a trip to Olean, 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 October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.0°F (-5.0°C)Light RainVery CloudyAverageSlightly High
February24.8°F (-4.0°C)Light RainVery CloudyAverageSlightly High
March32.9°F (0.5°C)Light RainMostly CloudyAverageAverage
April44.1°F (6.7°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly CloudyAverageAverage
June63.5°F (17.5°C)Light RainMostly SunnySlightly HighAverage
July68.4°F (20.2°C)Light RainMostly SunnySlightly HighAverage
August66.4°F (19.1°C)Light RainMostly SunnyAverageSlightly Low
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighSlightly Low
October49.3°F (9.6°C)Light RainMostly CloudySlightly LowAverage
November37.4°F (3.0°C)Light RainMostly CloudySlightly LowAverage
December30.0°F (-1.1°C)Light RainVery CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can really help, as prices can change frequently. Additionally, booking 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. We're here to help you find the best option for your needs.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your existing plans, and organize your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the natural landscape of Olean

The area's architecture and history are just a few of the reasons to vacation in Olean. Renowned for its restaurants, shopping and safari tours, this city welcomes all visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Olean

Are you hoping to find attractions to see while you're in town? Venture out of your vacation home and check out everything that Olean has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Holiday Valley Resort (17.5 mi / 28.1 km)
  • HoliMont (18.5 mi / 29.7 km)
  • Snow Pine Village (16.6 mi / 26.7 km)
  • Winery of Ellicottville (18.3 mi / 29.5 km)
  • Birch Run Country Club (5.1 mi / 8.1 km)
  • Watson's Chocolates (18.3 mi / 29.4 km)

Exploring the natural landscape of Olean

Whether you're looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Olean. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Cuba Lake (13.7 mi / 22.1 km)
  • Gargoyle Park (2.2 mi / 3.6 km)
  • Rock City Park (5 mi / 8.1 km)
  • Potato Creek Trailhead (17.5 mi / 28.1 km)
  • Nannen Arboretum (18.6 mi / 29.9 km)

Transportation to and around Olean

The nearest airport is in Olean, NY (OLE-Cattaraugus County), located 11.5 mi (18.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Bradford, PA (BFD-Bradford Regional), which is 22.2 mi (35.8 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Olean?
Prices for vacation rentals in Olean 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 Olean 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 Olean vacation house rentals?
You can find great discounts on house rentals in Olean 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 Olean ski resort rentals?
For those looking for ski resort rentals near Olean, the closest major ski area is Holiday Valley, located about 20 miles away in Ellicottville. This charming village offers a variety of vacation rentals, including cozy chalets and condominiums that are ideal for families and groups. Many properties in Ellicottville boast amenities such as fully equipped kitchens, spacious living areas, and outdoor decks, great for relaxing after a day on the slopes.

In addition to the ski accommodations, Ellicottville is known for its vibrant downtown area, featuring local shops, restaurants, and entertainment options. Visitors can enjoy après-ski activities at nearby bars and eateries, which often host live music and events during the winter months. For those seeking a more rustic experience, cabins in the surrounding countryside provide a peaceful retreat, often equipped with fireplaces and hot tubs, enhancing the overall mountain getaway experience.

For travelers interested in exploring beyond skiing, the area offers various winter activities, including snowshoeing and cross-country skiing, with many rentals providing easy access to trails.
What is the most popular type of vacation rental accomodation in Olean?
In Olean, vacation houses are the most popular type of rental, with several available throughout the area. These houses typically provide ample space, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas where families and groups can gather. Many also come with outdoor spaces like patios or gardens, superb for enjoying the fresh air. Additionally, there are several apartments and cottages in Olean, offering travelers a cozy and home-like atmosphere.
Are there any family house rentals in Olean?
In Olean, New York, there are several family-friendly vacation rentals available, making it a great destination for those traveling with children. Accommodations in the area often feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces where kids can play and explore. Many homes come with amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for all guests.

Visitors can enjoy local attractions such as the nearby Allegany State Park, which offers opportunities for hiking, picnicking, and wildlife viewing, or take a stroll through the charming downtown area with its shops and eateries.
Can I find long-stay vacation rentals in Olean?
A long-stay vacation rental in Olean 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 Olean?
In Olean, there are several pet-friendly house rentals available, providing a comfortable stay for travelers with furry companions. Many of these vacation homes come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can play.

The area offers a quaint, small-town feel, with close proximity to parks and green spaces ideal for walking dogs. Nearby, the Allegany State Park is a great spot for outdoor adventures, offering hiking trails and scenic views that can be enjoyed with pets.
Are there any remote work vacation rentals in Olean?
In Olean, New York, there are several vacation rentals suitable for remote work. These properties often come equipped with essential amenities such as high-speed Wi-Fi, work desks, and comfortable living spaces, allowing for a productive environment while enjoying your stay. Many rentals also offer additional features like access to public areas with free Wi-Fi, ensuring that you can stay connected during your visit. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Olean vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Olean 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 Olean?
In Olean, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals. Many rentals also feature blenders for making smoothies or other blended drinks. Onsite parking is commonly available, providing convenience for those traveling with vehicles. Additionally, several properties are pet-friendly, accommodating travelers who wish to bring their furry companions along. Air conditioning is another sought-after amenity, ensuring comfort during the warmer months.
When is the best time to visit Olean for a vacation rental?
The peak travel season in Olean stretches from June to August, with July being the most popular month for visitors. During this vibrant period, travelers flock to the city to enjoy outdoor activities, beautiful landscapes, and local events. The warm temperatures, typically in the mid-70s to low 80s Fahrenheit, create a friendly space superb for exploring parks, hiking trails, and enjoying local festivals.

If you're planning to experience Olean at its liveliest, July is an excellent choice. The community comes alive with various events, and the warmer weather enhances opportunities for sightseeing and outdoor adventures, making it a great time for families and friends to connect.

For those seeking a more budget-friendly option, consider visiting in December. While this month may be quieter in terms of tourist activity, it offers a unique charm with holiday festivities and the opportunity to experience the city in a different light. You can enjoy cozy indoor attractions and the beautiful winter scenery without the crowds.

Ultimately, the best time to visit Olean for a vacation rental will depend on your personal preferences—whether you're drawn to the bustling summer months filled with activity or the peaceful atmosphere of the winter season.
How early should I book a Olean vacation rental?
Book your Olean 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 Olean, New York, United States of America?
In Olean, visitors can enjoy a variety of attractions that highlight both the natural beauty and the local culture of the area. The scenic Allegheny River and its surrounding parks offer opportunities for outdoor activities such as hiking, fishing, and picnicking. Nearby, the Rock City Park features impressive rock formations and scenic views, making it a great spot for nature enthusiasts.

For those interested in history, the Olean Historical Society Museum showcases the region's rich heritage with exhibits and artifacts. The town also celebrates its local arts scene, particularly through events held at the Olean Theater Workshop, which offers a range of performances throughout the year.

Additionally, the nearby Allegany State Park provides expansive recreational opportunities, including trails for hiking and biking, as well as camping facilities for those looking to immerse themselves in the great outdoors.
Can I change or cancel my Olean home rental booking on Vrbo?
To find Olean 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 Olean 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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