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.

Ski-in/out Condo, King Bed + Fireplace

This 1-bedroom ski-in/ski-out condo (with a king bed!) and full bathroom is perfect for a couple or a small family. Freshly renovated in September 2023 with new paint, furniture, and kitchen updates. Walk or ski to the SnowPine and Sunrise lifts at Holiday Valley, just a few miles from town. An hourly shuttle can take you to the main lodge. Enjoy easy access to mountain biking and hiking trails in the summer. Includes parking, a gas fireplace, high-speed internet, Roku TV, and access to shared l

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!

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!

Hidden Haven, 6 mi. outside EVL

Welcome to The Hidden Haven, nestled in the heart of the Enchanted Mountains of WNY, just outside of EVL, NY. If you're looking to stay close to town, but outside the chaos, this is the place. It's less than 10 min, almost a straight shot, to town and the slopes at Holiday Valley and Holimont. This apartment is hidden in the barn of an old dairy farm, adjacent to the main house. You'll be able to enjoy your own quiet hideout as well as the scenic drive through the valley on your way to town.

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.

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

Houghton Brookside Retreat

Relax in this spacious, serene space, surrounded by nature. Enjoy your morning coffee on the large deck. Perfect for a get-away; close to hiking, hunting, fly fishing, skiing. Walking distance to Houghton University. In the well appointed and stocked kitchen you will be greeted by homemade bread, coffee, fruit, and breakfast essentials. This private space is on the lower level so guests must be able to navigate a set of stairs. Off-street parking.

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!!

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.

Studio Condo in the Wildflower Townhouses

A cozy studio with that extra touch! Minutes from Holiday Valley Ski Resort/Sky High Adventure Park/Golf Course. Shuttle service to the slopes during the ski season. Walking distance to town, restaurants, shops Biking trails. 20 Minutes from the Seneca Allegany Casino. Lyft and Uber services available.