Family-friendly holiday rentals in Olean

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, visiting your college student at Houghton University (walking distance), hiking in Letchworth State Park, antiquing in Angelica or Cuba. 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.

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.

Ski In/Out Condo, King Bed

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!

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

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.

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

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

Glamping at the Farm

-We invite you to come be a happy "Glamper" and have a unique farm experience. The Glamper has everything you will need. It is located near our barns and play area, has a stunning view of the valley. -5 minutes from Lime Lake, 20 minutes from Ellicottville, 45 minutes from Buffalo, and 65 minutes from Niagara Falls. -Outdoor area includes a picnic table, small grill, and a fire pit. Tents are allowed (tent rental available at the farm). Open May 1 - October 13.

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!!