Vacation rentals in Olean

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Top-rated vacation rentals in Olean

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

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Top guest favorite
Tiny home in Machias
4.87 out of 5 average rating, 447 reviews

Lucky Day Cabin Ellicottville/Ashford 30 acres

Family built cabin on 30 acre country estate, just outside exciting year round resort village of Ellicottville. Perfect for nature lovers and outdoor enthusiasts, the cabin has all necessities, similar to a tiny house. Nestled near the gardens, and surrounded by quiet rolling hills. Enjoy with door step delivered breakfast, or book a guided hike with estate owner and learn about medicinal plants and flowers, the topography of the land and a farm fresh picnic lunch on the peninsula of our lake.

Top guest favorite
Condo in Ellicottville
4.91 out of 5 average rating, 173 reviews

Ski-in/out Condo, King Bed + Fireplace

Welcome to your perfect getaway in Holiday Valley! This recently renovated condo offers a comfortable retreat with a private bedroom (king bed), a lofted sleeping area (queen bed and twin bunks), and a full bath. Enjoy the convenience of keyless entry, dedicated parking, WiFi, cable TV, and in-unit laundry. Relax on the patio with seating for four, and make the most of the on-site A/C—perfect for both summer and winter stays. Nestled right next to the SnowPine lift, this condo is a winter sport

Superhost
Guesthouse in Olean
4.86 out of 5 average rating, 184 reviews

Cozy Country Get Away Suite

If you're passing through town on your travels or a local looking for a private get away, this is the perfect place to kick back, relax and enjoy some peace and quiet. You can sit by the fire, look across to see fireflies in the field or tilt your head back to have an amazing star-gazing experience. A one of a kind property to make memories with friends, family, or for a special romantic get away. Access to 93 acres with trails to walk or mountain bike on, fields to wander through and wildlife.

Top guest favorite
A cabin is nestled among tall trees in a vibrant forest displaying autumn colors. The structure is partially obscured by greenery, and light filters through the leaves, creating a tranquil setting in nature.
Cabin in Ellicottville
4.95 out of 5 average rating, 141 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.

Guest favorite
Loft in Olean
4.96 out of 5 average rating, 156 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!

Superhost
A row of charming townhomes is reflected in a serene pond, showcasing a series of gabled roofs and spacious balconies. Lush green grass surrounds the homes, providing a natural and inviting setting amidst the tranquility of the landscape.
Townhouse in Ellicottville
4.8 out of 5 average rating, 171 reviews

★ SKIING, HIKING, VILLAGE OF EVILLE MTN ESCAPE ★

Snugly nestled at the foot of the Ellicottville mountains, this Wildflower townhome provides easy access to skiing (across the street from Holiday Valley), hiking, fishing, golf and a whole host of nature activities. With the village of Ellicottville only a 15-20 minute walk (or very short drive) away, the nearby comforts of civilization include plentiful shops, restaurants and other attractions. You can't beat this location if you are looking for a relaxing retreat from the hustle and bustle.

Guest favorite
The cottage exterior features a stone façade, complemented by a welcoming porch and large windows. Greenery surrounds the entrance, with potted plants adding a touch of life. The front door, framed by glass panels, offers a glimpse into the cozy interior.
Cottage in Olean
4.83 out of 5 average rating, 191 reviews

Artists cottage - mid century

The perfect spot to relax, read, write meditate. View birds, wildlife in an old forest along the Allegany River from the porch, deck or large picture windows. Take a walk. (fast Wi Fi, 32 inch TV and echo dot) Families and dog owners will like the large yard (no fence, warning ticks and Lyme disease in the area). My grandmother designed the cottage around a vintage house trailer (tiny house)1956. There are many unique and cleaver features. Family mementos through history are on display.

Top guest favorite
Loft in Coudersport
4.99 out of 5 average rating, 272 reviews

Main Street Lofts - King Suite

Cozy up in this spacious, newly renovated downtown historic building! Our king suite offers a king bed with a luxurious bathroom! HUGE walk-in shower with double vanities! We take pride in keeping our spaces extremely clean and our guests appreciate that! Step out the front door and all of our great shops and restaurants will be just a few steps away. Whether you are coming to stargaze at cherry springs or hike the Pennsylvania Grand Canyon, this is a great place to start your adventure!

Top guest favorite
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, 169 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 favorite
The living room features a comfortable brown sofa and a red accent chair, complemented by a round coffee table. Natural light enters through sliding doors, connecting to an outdoor area. Nearby, a modern fireplace is visible, along with rustic wall art and wooden accents.
Condo in Ellicottville
4.89 out of 5 average rating, 362 reviews

Ski-in/out Condo, King Bed + Fireplace

Enjoy a cozy, renovated condo at SnowPine Village. True ski-in/ski-out access in winter! Perfect for summer adventures. ⛷️ Ski-in/ski-out 🛏 King bed + loft w/ bunks – Sleeps 6 🍳 Fully stocked kitchen 📶 Fast WiFi + Roku TVs 📍 Short drive to Ellicottville & Holiday Valley 🚙 Ample parking (2-car limit in ski season) 🏡 Covered patio w/ grill & seating ☀️ Great for hiking & outdoor fun 🏓 Pickleball courts on-site ❄️ Mini-split A/C – Stay cool in summer

Top guest favorite
A charming cabin with a wooden exterior is set against a green lawn. The structure features multiple windows, allowing natural light to enter. A small staircase leads to the entrance, while a fenced yard surrounds the property, offering a sense of privacy and space.
Barn in Cuba
4.98 out of 5 average rating, 208 reviews

Stylish & Inviting, Close to lake, 1BR-Sleeps 2

This unique place has a style all its own. This 1BR space "delivers" when it comes to comfort and convenience. Comes with a fully equipped kitchen and all the amenities to make your stay as comfortable and easy as possible. Has a deck if you would like to just relax or enjoy a meal. This cozy space is on the second story so if you have a hard time with stairs sadly we aren't the place for you. Try us out, you won't be disappointed!!

Top guest favorite
A small balcony features a table surrounded by two chairs, accented with orange cushions. The scene is illuminated by moonlight, highlighting a distant mountain and well-kept landscaping. Soft lighting casts a warm glow on nearby homes, creating a serene nighttime atmosphere.
Condo in Ellicottville
4.96 out of 5 average rating, 151 reviews

Mountain View at Wildflower walk to town 1 BR loft

Across from Holiday Valley this mountain view home has everything you need for a memorable stay in Ellicottville. A short walk to town. Walk or take the shuttle to the slopes. An ideal place to getaway and relax with family and friends. All the amenities of home. Just bring your favorite food and beverages and leave the rest to us. A well-appointed kitchen, comfy beds and nothing to do but enjoy your stay. License# T-RENT26-00014

Popular amenities for Olean vacation rentals

When is the best time to visit Olean?

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Avg. price$98$99$101$96$104$109$122$115$105$115$140$114
Avg. temp26°F28°F35°F47°F59°F68°F72°F70°F63°F52°F41°F32°F

Frequently Asked Questions

  • Do apartment rentals in Olean have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Olean. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Olean?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Olean have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Olean. Enjoy a tailored experience with all the comforts you desire.

  • Are there house rentals with a dedicated workspace in Olean?

    Yes! Work meets play with ease at over 10 house rentals in Olean featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Olean?

    Olean has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Olean?

    Four-legged friends are welcome in Olean. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Olean have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Olean. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Olean?

    Experience the best of Olean with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about vacation rentals in Olean

  • Total vacation rentals

    Explore 50 vacation rentals in Olean

  • Nightly prices starting at

    Olean vacation rentals start at $50 per night before taxes and fees

  • Verified guest reviews

    Over 2,050 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Olean vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Olean rentals

  • 4.8 Average rating

    Olean stays are highly rated by guests—averaging 4.8 out of 5!

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