Holiday rentals in Olean

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

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.

Ski In/Out Condo, King Bed

This 1 bedroom (King bed!) and full bathroom ski-in/ski-out condo is perfect for one couple or a small family. Freshly renovated in September 2023 (paint, furniture, kitchen). Walk/ski to the SnowPine and Sunrise lifts at Holiday Valley and only a few miles from town. Shuttle available on the hour to take you to the main lodge. Easy access to mountain bike and hiking trails in the summer. Parking, gas fireplace, high-speed internet, Roku cable TV and laundry included. Easy, keyless check-in.

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.

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 Four Flat

Welcome to “The Four Flat”! Nestled in a quiet neighborhood, our place 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 and modern living room with a 55-inch 4K Smart TV and L-shaped sofa for extra sleeping space. **All new heating and cooling updates for added comfort**

Woodland Streamside Glamping

Enjoy relaxing days and nights in this private glamping outfitters tent nestled in the woods alongside a babbling brook. This glamp site includes a queen size bed, lounging furniture, bar table and stools, food prep table with Keurig, wood stove and propane heat, campfire ring, solar battery electricity, a seperate bathroom tent and hot shower. Parking is 100 steps from the site. Everything you need to recharge and enjoy a cozy outdoor getaway.

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!!