Vacation rentals in Olean

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.

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!

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

Serenity Creek

Clean and comfortable space to relax and enjoy the country area, just 8 miles from Ellicottville. Fully stocked kitchen! High-Speed WiFI with Smart TV. Country home in a quiet setting. Most people will have adequate cell service for text/talk. Enjoy watching the beautiful horses grazing the pastures of Whisper Mountain Ranch, right next door! Please message me if you would like more information on reserving a guided trail ride through the rolling hills behind this peaceful property.

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

The King Loft

Welcome to “The King Loft”! Nestled in a quiet neighborhood, our loft offers upscale comfort and convenience. Just 1 mile from Olean General Hospital and 3 miles from St. Bonaventure University. Also discover the charming town of Ellicottville, only 20 miles away. Comfortable living space: Relax in the cozy living room which has a comfy bean bag and futon for extra sleeping space. Also enjoy the new 50 inch Smart TV. **YouTubeTV now available**

The Lookout

Welcome to your perfect getaway nestled in the heart of Olean, NY! Whether you're looking to unwind in nature or explore the charm of this quaint town, our spacious and comfortable 1-bedroom unit is your ideal base. Whether you're here for a peaceful retreat or an adventurous weekend, our Airbnb provides everything you need for a memorable stay. Book now and experience the warm hospitality of Olean, New York!

King Bed, A/C, Pickleball, Patio w/ Grill

Upscale SnowPine Village condo, perfect for outdoor fun and year-round relaxation. 🛏️ King Bed 🍳 Fully stocked kitchen 🏡 Private Patio with seating & grill ❄️ Portable A/C in each room 🛁 2 Full Baths 📶 Fast WiFi + 55” Roku TV 🏓 Pickleball Court Nearby 📍 Minutes to Town – Close to shops & dining 🔥 Electric Fireplace ⛷️ Ski-In/Ski-Out – Patio gate to slopes 🚗 Ample Parking – Limit 2 during ski season

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 Starlink internet.