Holiday rentals in Olean

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Top-rated holiday rentals in Olean

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A wooden structure is nestled among tall trees, illuminated by warm light from within. The night sky is filled with stars, including the Milky Way, casting a serene atmosphere over the surrounding landscape.
Farm stay in Coudersport
4.99 out of 5 average rating, 132 reviews

Glamping & Stargazing at Olga Farm

Olga Farm is an absolutely lovely place in the heart of the Pennsylvania Wilds. We're blessed to have this farm & love to share it with others. We have a private stargazing field where we host primitive campers...Glamping at Olga Farm is a step up from that in that you don't need to worry about a tent, but it still is essentially camping. Breath taking sunrises, a lovely organic vegetable garden & farm, & dark skies at night round out what makes Glamping at Olga Farm an unforgettable experience!

Top guest favourite
Cabin in Ellicottville
4.96 out of 5 average rating, 166 reviews

Stylish & Secluded Hideaway, 5 mins to EVL

This private space is quietly tucked away in a stand of pines in the woods alongside Bryant Hill Creek. A wall of windows brings nature and natural light pouring into the space, and a fully-equipped kitchen and European bathroom provide modern comfort. Less than 4 miles outside of E-ville, it comfortably sleeps 2 adults and offers a chic and romantic setting for a couple to hide away with easy access to downtown. 4x4 a must in the snow, or simply park at the foot of the driveway. Tv & wifi.

Top guest favourite
Loft in Olean
4.96 out of 5 average rating, 162 reviews

Joe's Cozy Loft

Joe's Cozy Loft is now under new management! Expect the same great accommodations and amenities as before but with seamless and Superhost service. Your stay with us includes wifi, off street parking after business hrs, a luxurious 2 person jet tub, laundry capabilities, a private deck with grill and more. We are a short walk or drive to many local restaurants and taverns. We are nestled in the heart of the the Enchanted Mountains with easy access to Ellicottville skiing, Buffalo and much more!

Top guest favourite
Cottage in Great Valley
4.95 out of 5 average rating, 171 reviews

Country get away

Beautiful private country setting. Perfect spot to take in the fall foliage and count the stars as you sit around the fire. Newly remodeled cozy country cottage . Full kitchen and washer and dryer available . Perfect get away from the hustle and bustle of the city . Central location to all of the area attractions like Holiday Valley ski resort , Ellicottville shopping and restaurants and Seneca Allegany casino. WiFi and dish network provided in a clean and sanitized space. Gas grill available

Guest favourite
Home in Ellicottville
4.85 out of 5 average rating, 240 reviews

Riverside Retreat 3BR-Games Room-Hot Tub-Fire Pit

Escape to the peacefulness of farm country, just seven minutes from Ellicottville. Our secluded three-bedroom, three-bath home offers stunning escarpment views from the outdoor patio with a hot tub, fire table, fire pit, and BBQ. Inside, enjoy fully furnished rooms and a modern kitchen, complete with a cozy gas fireplace. Our retreat is ideal for families, couples, and groups looking for comfort and convenience. Conveniently located for outdoor activities at nearby Holiday Valley & Holimont.

Top guest favourite
The cabin exterior features natural wood shingles and large windows, providing a warm and inviting appearance. A stone pathway leads to the entrance, bordered by well-maintained landscaping and vibrant plants, surrounded by greenery that enhances the tranquil setting.
Home in Mount Jewett
5 out of 5 average rating, 111 reviews

The Hills and The Holler (Westline)

Our tranquil retreat nestled in the heart of The Allegheny Forest, where every season offers its own enchantment.A cozy yet spacious cabin boasts rustic charm and modern comforts, perfect for a serene getaway any time of year. Whether you're seeking adventure on nearby hiking trails, serene moments by the creek, or starlit nights under the clear skies, our home offers it all. With ample room for families or groups, and a short drive to local attractions, your unforgettable experience awaits

Top guest favourite
A spacious living area is highlighted by a large brown leather sectional sofa adorned with decorative pillows. A vintage wooden trunk serves as a coffee table, topped with a lantern, a decorative orb, and a small plant. Soft light filters through sheer curtains.
Home in Allegany
4.96 out of 5 average rating, 176 reviews

Stylish 3-bedroom home near Ellicottville, NY

Stylish, entire residential 3 bedroom/ 1 bath home. Close to Ellicottville/skiing -30 mins., St. Bonaventure University, Cutco, Rock City Park, Allegany State Park, kayak launch, biking, and walking trail. Niagara Falls is a 1.5-hour drive, Zippo 30 minutes. Walmart and movie theater are 2 miles away. Many restaurants are nearby. A seasonal 2 screen drive-in movie theater-20 min. drive. 2 queen beds , 1 double bed, and a chair converts to a twin size bed. Fully equipped kitchen.

Guest favourite
Flat in Olean
4.97 out of 5 average rating, 103 reviews

Henley Hideaway

Centrally located to downtown Olean, this 2 bedroom unit is sure to make you feel at home! Enjoy easy access to local restaurants, Four Mile Brewery, and the Allegheny River Trail for a bike ride or scenic walk. Includes free Wi-Fi, off-street parking, a fenced in yard, on site laundry, a full kitchen and more. Close to St. Bonaventure University, 30 min drive to Ellicottville & Holiday Valley. This is the back unit and will share a driveway with any guests staying in the front unit

Top guest favourite
Chalet in Ellicottville
4.97 out of 5 average rating, 264 reviews

Firefly Chalet

Ideal private chalet getaway in Ellicottville NY. The property is located at the top of a hill on a private drive, giving you a beautiful overlook of the valley. The location is a 5 min drive to downtown Ellicottville and 3min drive to Holiday Valley. There are many state land hiking trails off of the private drive. Convenient location for families looking to ski for the weekend, hike locally/at Allegany State Park, and visit the beautiful town of Ellicottville NY.

Top guest favourite
Cottage in Fillmore
4.97 out of 5 average rating, 126 reviews

The Ridge Airbnb and Campground

Grandma‘s cottage (1250 sq ft) with some modern necessities and upgrades! Welcome to “The Ridge.” Enjoy a large creek a two minute walk away. Minutes to Houghton college. Letchworth State Park 21 min🏔️ 11 min Rushford Lake, there is public beach. 15 min to Arcade . We are Dog friendly! We always aim for five star service 🙂 I do ask that you list the number of guests .And if it’s one, it’s 1 and if it’s six it’s 6 🙃. P.S. We have 16 new ducklings! 🦆

Top guest favourite
A small log cabin is presented featuring an inviting front porch with a railing. Solar panels are visible on the roof. The surrounding area includes greenery and a gravel pathway, contributing to the rural setting.
Cabin in Great Valley
4.91 out of 5 average rating, 339 reviews

The Porcupine, featuring fiber optic internet

* Get Away From it all The Porcupine is a small, comfortable and private log cabin. And and we are proud to be solar powered! Great for a couple or a family with small children. Rural setting great for hikes or bikes. 3 miles to the village of Ellicottville. 8 miles to the Seneca Allegany Casino. And 2 miles to the slopes of Holiday Valley

Top guest favourite
Flat in Great Valley
4.88 out of 5 average rating, 298 reviews

Cozy apartment tucked into the forest (with sauna)

Nestled in the forest only seven minutes’ drive from Holiday Valley, this contemporary style self-contained apartment is the perfect weekend getaway for skiing and nature-loving couples. With every luxury and convenience including a sauna, you can home cook meals or barbecue on the deck, with nothing but forest beyond, relax and watch a movie on our LCD screen or use high speed internet on cable.

Popular amenities for Olean holiday rentals

When is the best time to visit Olean?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price₹9,845₹10,609₹9,940₹9,176₹9,940₹10,418₹11,661₹10,992₹10,036₹10,992₹13,381₹10,896
Avg. temp-3°C-2°C2°C8°C15°C20°C22°C21°C17°C11°C5°C0°C

Frequently Asked Questions

  • What are the best places to stay in Olean?

    Stays near downtown Olean provide easy access to local shops, restaurants, and cultural sites, while places around the outskirts have quieter, more scenic settings. Rentals in residential neighborhoods often include home-like comforts.

  • What are the best things to do in Olean with kids?

    Explore Olean’s playgrounds, hands-on museums, or nearby nature trails, which frequently appeal to families. The area also has bowling alleys and family-friendly events during the year.

  • What are some of the best things to do in Olean?

    Wander Olean’s historic downtown, browse local shops, or visit the Cutco-Ka-Bar Visitors Center to learn about local industry. Outdoor spaces like Franchot Park and nearby trails are frequently suggested for spending time outside.

  • How is the weather in Olean?

    Olean has cold winters, with temperatures averaging 18–35°F (-8–1°C) and frequent snowfall, while summers are warm, reaching 79–83°F (26–28°C) with increased rainfall. Spring and autumn bring milder weather and changing foliage.

  • When is the best time to visit Olean?

    Late spring through early autumn is often recommended for outdoor activities, mild temperatures, and local events. Winter appeals to those interested in holiday celebrations and snowy landscapes.

  • What are the best places to visit in Olean?

    Explore attractions like the Cutco-Ka-Bar Visitors Center, stroll around Franchot Park, or discover the area's historic downtown with local shops and art spaces. Nature enthusiasts often visit nearby state parks for hiking and relaxation.

  • What are some hiking trails in Olean?

    Olean has nature trails in its public parks and green spaces where you can explore wooded areas, creek views, and gentle elevation changes. For longer hikes, nearby state parks around the city also provide options for trail enthusiasts.

  • What are some family activities we can do in Olean?

    Families often enjoy picnics at public parks, visits to interactive museums, or taking part in seasonal events held in the community. Trails nearby frequently attract families interested in gentle outdoor adventures.

  • What are some of the best day trip ideas from Olean?

    Explore lush forests in nearby state parks, discover local history museums in surrounding towns, or enjoy regional wineries and small farm tours. Outdoor enthusiasts often head for scenic trails and peaceful lakes around the area.

  • Are there any pet friendly accommodations available in Olean?

    Pet friendly accommodations can be found across Olean, with many vacation rentals and some short-term stays welcoming pets. Several local parks and walking paths make it easy to enjoy the area with your dog.

  • What are some local tips for visiting Olean?

    Locals suggest exploring early in the day for quieter experiences and sampling small bakeries or diners for regional flavors. Community events and farmers markets are a welcoming way to connect with Olean’s spirit.

  • What is Olean known for?

    Olean is known for its history as a hub for industry and transportation, as well as its connection to outdoor recreation in western New York. The city also has roots in culinary tools manufacturing and local arts.

  • What are the best hidden gems to explore in Olean?

    Look for small art galleries, tucked-away coffee shops, or local antique stores nestled within Olean’s historic streets. Area trails and scenic overlooks also offer quieter spots beyond the main attractions.

  • What are the best foods to try in Olean?

    Try local specialties such as Western New York-style pizza, wings, and classic diner breakfasts, alongside seasonal produce from regional markets. Bakeries also feature distinct pastries and homemade goods.

  • What should I bring for a trip to Olean?

    Pack comfortable walking shoes, weather-appropriate clothing, and a rain jacket, as Olean has varying temperatures and occasional showers year-round. If you plan to hike, bring outdoor gear and sun protection.

  • What is the nightlife in Olean like?

    Olean has a laid-back nightlife scene, with neighborhood taverns, casual bars, and venues hosting live music or trivia nights. Local restaurants often feature relaxed atmospheres for gathering with friends or family.

  • What are the most popular events or festivals in Olean?

    Olean hosts seasonal festivals, including holiday parades, summer arts events, and community celebrations centered around food and music. The Strawberry Festival and Santa Claus Lane Parade are frequently mentioned annual highlights.

  • Are there family friendly vacation rentals in Olean?

    Olean has a range of family friendly vacation rentals, including whole homes, apartments, and guest suites. Many properties include extra amenities and location advantages for guests traveling with children.

Quick stats about holiday rentals in Olean

  • Total holiday rentals

    Explore 50 holiday rentals in Olean

  • Nightly prices starting at

    Olean holiday rentals start at ₹3,823 per night before taxes and fees

  • Verified guest reviews

    Over 2,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Olean holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Olean rentals

  • 4.9 Average rating

    Olean stays are highly rated by guests – averaging 4.9 out of 5!

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  5. Olean