Holiday rentals in Olean

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Top-rated holiday rentals in Olean

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Guest favourite

Guest house in Olean

4.85 out of 5 average rating, 168 reviews

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.

Guest favourite

Apartment in Ellicottville

4.93 out of 5 average rating, 152 reviews

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

Guest favourite

Loft in Olean

4.96 out of 5 average rating, 143 reviews

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!

Top guest favourite

Cottage in Great Valley

4.95 out of 5 average rating, 152 reviews

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

Guest favourite

Home in Allegany

4.96 out of 5 average rating, 153 reviews

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.

Guest favourite

Home in Great Valley

4.91 out of 5 average rating, 122 reviews

Serenity Creek

Clean and comfortable space to relax and enjoy the country area, just 8 miles from Ellicottville. Fully stocked kitchen! High-Speed WiFI with Smart TV. Country home in a quiet setting. Most people will have adequate cell service for text/talk. Enjoy watching the beautiful horses grazing the pastures of Whisper Mountain Ranch, right next door! Please message me if you would like more information on reserving a guided trail ride through the rolling hills behind this peaceful property.

Top guest favourite

Flat in Port Allegany

4.98 out of 5 average rating, 184 reviews

Two bedroom apartment

Well-appointed, two bedroom apartment. Hardwood floors through out. All of the comforts of home are included. There's even a play loft for children! Country setting with lovely views of the surrounding hills and pond. Set in the heart of the Allegheny Mountains. Near by attractions include Allegany State Park(31 miles), Kinzua Bridge(22 miles), Cherry Springs State Park (32 miles), Ellicottville NY, ski country (47 miles) Just a few miles from The Four Sisters wedding venue.

Guest favourite

Chalet in Ellicottville

4.97 out of 5 average rating, 230 reviews

Firefly Chalet

Ideal private chalet getaway in Ellicottville NY. The property is located at the top of a hill on a private drive, giving you a beautiful overlook of the valley. The location is a 5 min drive to downtown Ellicottville and 3min drive to Holiday Valley. There are many state land hiking trails off of the private drive. Convenient location for families looking to ski for the weekend, hike locally/at Allegany State Park, and visit the beautiful town of Ellicottville NY.

Guest favourite

Flat in Olean

4.9 out of 5 average rating, 58 reviews

Contemporary Comfort at 208

Charming lower level apartment. Close to downtown Olean, Rock City Park & South Union Street Launch for kayaking, and movie theatre. About 2 miles from St Bonaventure University. Ellicottville/Holiday Valley, Allegany State Park and Seneca Allegany Casino are within reasonable driving distance. Fully equipped kitchen. The master bedroom has a king size bed and the side room has a pull out twin loveseat to sleep 1. No pets and no smoking!

Top guest favourite

Barn in Cuba

4.98 out of 5 average rating, 180 reviews

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!!

Guest favourite

Apartment in Ellicottville

4.93 out of 5 average rating, 100 reviews

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

Upscale SnowPine Village condo, perfect for outdoor fun and year-round relaxation. 🛏️ King Bed 🍳 Fully stocked kitchen 🏡 Private Patio with seating & grill ❄️ Portable A/C in each room 🛁 2 Full Baths 📶 Fast WiFi + 55” Roku TV 🏓 Pickleball Court Nearby 📍 Minutes to Town – Close to shops & dining 🔥 Electric Fireplace ⛷️ Ski-In/Ski-Out – Patio gate to slopes 🚗 Ample Parking – Limit 2 during ski season

Guest favourite

Guest suite in Great Valley

4.92 out of 5 average rating, 389 reviews

Comfy studio nestled in the woods (New Listing)

Nestled in the forest only seven minutes’ drive from Holiday Valley, this contemporary style self-contained studio apartment is the perfect weekend getaway for skiing and nature-loving couples. With every luxury and convenience, you can home cook meals or barbecue on the deck overlooking the creek, with nothing but forest beyond. Relax and watch a movie on our LCD screen or use high speed Starlink internet.