Family-friendly holiday rentals in Olean

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.

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.

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.

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.

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!

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.

The Nook at SnowPine Village Ski-in/Ski-out Condo

The Nook is a convenient ski in/ski out condo tucked into the southeast hills of Holiday Valley. It is seconds from the slopes with views of the Snow Pine chair lift and Double Black Diamond Golf Course. Our condo is an updated 1 bedroom, 1 bathroom unit with AC (summer only), fireplace, a pull-out sofa and king bed. It's great for a couple or small family fitting 2-4 people. The Nook is minimal yet cozy — the perfect place to rest and recharge after any adventure.

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

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!!

Ski In-Out Condo at Holiday Valley

Newly Painted & Newly Furnished. Warm fireplace in a cozy ski in/out condo. Full kitchen and all the dishes and amenities of home. Parking for guests, laundry facilities, fast wifi, and easy access to the surrounding area. Snowpine chairlift is short walk, as is The Wall ski run. Relax in our condo without the need to drive to the resort, and fight the crowds. Downtown Ellicottville is only a few minutes away by car.