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

Welcome to your perfect getaway in Holiday Valley! This recently renovated condo offers a comfortable retreat with a private bedroom (king bed), a lofted sleeping area (queen bed and twin bunks), and a full bath. Enjoy the convenience of keyless entry, dedicated parking, WiFi, cable TV, and in-unit laundry. Relax on the patio with seating for four, and make the most of the on-site A/C—perfect for both summer and winter stays. Nestled right next to the SnowPine lift, this condo is a winter sport

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.

Loft Condo in Wildflower

This is a ground level loft condo that is bright, clean and nicely updated. We are minutes from the Holiday Valley Resort and a short walk to the Village of Ellicottville. This condo offers AC for the summer and a gas fireplace for the winter. We have complimentary coffee and tea with cream and sugar on site. Kitchen is equipped with some spices, oils and cookware. We also supply clean linens and towels. This place is great for 2 to 6 guest for family or close friends with 3 beds and a futon .

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.

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 Oak Hill Historic District Hideaway

A guesthouse loft behind a Pre-war Tudor in the Oak Hill Park Historic District in the heart of Olean with a private entrance & address. More spacious than a hotel room with a full kitchen, washer/dryer, A/C, heat, Wi‑Fi and driveway parking. Walkable to downtown shops & restaurants, short drive to St Bonaventure & the hospital. Ideal for solo visits, work trips or couples seeking comfort and value. Note: One flight of stairs, sleeps 3 max - One queen bed and rollaway cot.

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!!