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, 170 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

Loft in Olean

4.96 out of 5 average rating, 146 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!

Guest favourite

Apartment in Ellicottville

4.91 out of 5 average rating, 271 reviews

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

Enjoy a modern condo at SnowPine Village—perfect for summer hiking and offering true ski-in/ski-out access when the snow falls! 🛏 King bedroom + loft w/ bunks & full bed – Sleeps 6 🍳 Fully stocked kitchen 🏓 Pickleball courts on-site ❄️ Mini-split A/C – Stay cool in summer 🏡 Covered patio w/ grill & seating 📶 High-speed WiFi + Roku TVs 📍 Minutes to Ellicottville & Holiday Valley fun ⛷️ Ski-in/ski-out winter 🚙 Plenty of parking (2-car limit in ski season) ☀️ Great for hiking & outdoor fun

Top guest favourite

Cottage in Great Valley

4.95 out of 5 average rating, 153 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, 154 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, 124 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.

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, 60 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, 182 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

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.

Guest favourite

Home in Olean

4.92 out of 5 average rating, 51 reviews

Henley Home

Centrally located to downtown Olean, this two bedroom unit is perfect for your visit. Enjoy easy access to local restaurants, 4 Mile Brewery, and the Allegheny River Trail for a bike ride or Scenic walk. Includes free Wi-Fi, off street parking, on site laundry, a full kitchen and more. Close to St Bonaventure University, 30 minute drive to Ellicottville and Holiday Valley.

Top guest favourite

Flat in Olean

4.95 out of 5 average rating, 55 reviews

Country Gentleman 2 bedroom furnished loft-#1

This cozy 2 bedroom loft comes furnished with queen bed and tv with closets and single bed in other. LR has cozy fireplace large tv, paintings around, air conditioning , kitchen and bathroom furnished with essentials. Private entry, off street parking,coffee pot, microwave dishes and pots and pans. Live edge bar for kitchen dining