Vacation rentals in Olean

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Top-rated vacation rentals in Olean

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cabin in Ellicottville
4.96 out of 5 average rating, 168 reviews

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.

Top guest favorite
Condo in Ellicottville
4.95 out of 5 average rating, 380 reviews

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 .

Guest favorite
Loft in Olean
4.96 out of 5 average rating, 162 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 favorite
Cottage in Great Valley
4.95 out of 5 average rating, 171 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

Top guest favorite
A spacious living area is highlighted by a large brown leather sectional sofa adorned with decorative pillows. A vintage wooden trunk serves as a coffee table, topped with a lantern, a decorative orb, and a small plant. Soft light filters through sheer curtains.
Home in Allegany
4.96 out of 5 average rating, 176 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 favorite
Apartment in Olean
4.97 out of 5 average rating, 103 reviews

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

Top guest favorite
A spacious living room features a large sectional sofa adorned with a cozy blanket. A modern electric fireplace is mounted on the wall beneath a flat-screen TV, while a glass sliding door leads to a patio area with outdoor views.
Condo in Ellicottville
4.94 out of 5 average rating, 140 reviews

SnowPine Condo, King Bed, 2 Full Baths

Upscale SnowPine Village condo, perfect for outdoor fun and year-round relaxation. Ski-in/ski-out access when the snow falls! 🌿 Great for hiking, biking & outdoor adventure 🏌️ Golf & pickleball courts nearby 🏡 Private patio w/ seating & grill 🛏️ King, queen + trundle beds, sleeps 5 🛁 2 full baths 🔥 Electric fireplace 🍳 Fully stocked kitchen 📍 Minutes to town, close to shops & dining 📶 Fast WiFi + 55" Roku TV 🅿️ Ample parking (limit 2 during ski season) ❄️ Portable A/C

Superhost
The exterior of a charming two-story house is showcased, featuring light yellow siding and dark brown shutters. A wide front porch with white railings invites relaxation, while neatly trimmed green bushes line the walkway. Lush grass enhances the welcoming appearance of the property.
Home in Olean
4.83 out of 5 average rating, 120 reviews

Olean Ny 4 bedrms. entire house. St. Bonaventure

One 58 inch tv. 1940's home . Location is perfect! 2 miles from St. Bonnies.Rock City is close.Niagra Falls 1.5hr,Ellicotville, You can walk everywhere Pizza place across the street Grocery store is 3 blocks away and the movies &Walmart only a mile.Great restaurants stones throw away.We have a fire pit/ grill. Price depends on how many people. $15 per person per night over 5&must tell owner about extra day visitors and they are 5.00 per person. dog fee 35. a nt

Top guest favorite
The exterior of a modern chalet is shown, featuring a striking wooden facade with large triangular windows. Surrounded by lush greenery, the building is complemented by a stone walkway and simple outdoor seating, creating a peaceful entryway to the inviting natural surroundings.
Chalet in Ellicottville
4.97 out of 5 average rating, 264 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.

Top guest favorite
The kitchen features wooden ceilings and a modern design, with stainless steel and gray cabinets. Appliances include a refrigerator, stove, microwave, and coffee maker. A countertop area invites meal preparation, while decorative accents add a touch of style to the space.
Barn in Cuba
4.98 out of 5 average rating, 220 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!!

Top guest favorite
A small log cabin is presented featuring an inviting front porch with a railing. Solar panels are visible on the roof. The surrounding area includes greenery and a gravel pathway, contributing to the rural setting.
Cabin in Great Valley
4.91 out of 5 average rating, 339 reviews

The Porcupine, featuring fiber optic internet

* Get Away From it all The Porcupine is a small, comfortable and private log cabin. And and we are proud to be solar powered! Great for a couple or a family with small children. Rural setting great for hikes or bikes. 3 miles to the village of Ellicottville. 8 miles to the Seneca Allegany Casino. And 2 miles to the slopes of Holiday Valley

Guest favorite
A wooden deck is presented, surrounded by towering trees and lush greenery. A small table with two folding chairs is visible, offering a tranquil spot to enjoy nature. Sunlight filters through the leaves, creating a serene outdoor setting.
Guest suite in Great Valley
4.92 out of 5 average rating, 430 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 internet on cable.

Popular amenities for Olean vacation rentals

When is the best time to visit Olean?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,547 GYDG$23,220 GYDG$21,756 GYDG$20,083 GYDG$21,756 GYDG$22,802 GYDG$25,522 GYDG$24,057 GYDG$21,965 GYDG$24,057 GYDG$29,287 GYDG$23,848 GYD
Avg. temp-3°C-2°C2°C8°C15°C20°C22°C21°C17°C11°C5°C0°C

Frequently Asked Questions

  • What are the best places to stay in Olean?

    Stays near downtown Olean provide easy access to local shops, restaurants, and cultural sites, while places around the outskirts have quieter, more scenic settings. Rentals in residential neighborhoods often include home-like comforts.

  • What are the best things to do in Olean with kids?

    Explore Olean’s playgrounds, hands-on museums, or nearby nature trails, which frequently appeal to families. The area also has bowling alleys and family-friendly events during the year.

  • What are some of the best things to do in Olean?

    Wander Olean’s historic downtown, browse local shops, or visit the Cutco-Ka-Bar Visitors Center to learn about local industry. Outdoor spaces like Franchot Park and nearby trails are frequently suggested for spending time outside.

  • How is the weather in Olean?

    Olean has cold winters, with temperatures averaging 18–35°F (-8–1°C) and frequent snowfall, while summers are warm, reaching 79–83°F (26–28°C) with increased rainfall. Spring and autumn bring milder weather and changing foliage.

  • When is the best time to visit Olean?

    Late spring through early autumn is often recommended for outdoor activities, mild temperatures, and local events. Winter appeals to those interested in holiday celebrations and snowy landscapes.

  • What are the best places to visit in Olean?

    Explore attractions like the Cutco-Ka-Bar Visitors Center, stroll around Franchot Park, or discover the area's historic downtown with local shops and art spaces. Nature enthusiasts often visit nearby state parks for hiking and relaxation.

  • What are some hiking trails in Olean?

    Olean has nature trails in its public parks and green spaces where you can explore wooded areas, creek views, and gentle elevation changes. For longer hikes, nearby state parks around the city also provide options for trail enthusiasts.

  • What are some family activities we can do in Olean?

    Families often enjoy picnics at public parks, visits to interactive museums, or taking part in seasonal events held in the community. Trails nearby frequently attract families interested in gentle outdoor adventures.

  • What are some of the best day trip ideas from Olean?

    Explore lush forests in nearby state parks, discover local history museums in surrounding towns, or enjoy regional wineries and small farm tours. Outdoor enthusiasts often head for scenic trails and peaceful lakes around the area.

  • Are there any pet friendly accommodations available in Olean?

    Pet friendly accommodations can be found across Olean, with many vacation rentals and some short-term stays welcoming pets. Several local parks and walking paths make it easy to enjoy the area with your dog.

  • What are some local tips for visiting Olean?

    Locals suggest exploring early in the day for quieter experiences and sampling small bakeries or diners for regional flavors. Community events and farmers markets are a welcoming way to connect with Olean’s spirit.

  • What is Olean known for?

    Olean is known for its history as a hub for industry and transportation, as well as its connection to outdoor recreation in western New York. The city also has roots in culinary tools manufacturing and local arts.

  • What are the best hidden gems to explore in Olean?

    Look for small art galleries, tucked-away coffee shops, or local antique stores nestled within Olean’s historic streets. Area trails and scenic overlooks also offer quieter spots beyond the main attractions.

  • What are the best foods to try in Olean?

    Try local specialties such as Western New York-style pizza, wings, and classic diner breakfasts, alongside seasonal produce from regional markets. Bakeries also feature distinct pastries and homemade goods.

  • What should I bring for a trip to Olean?

    Pack comfortable walking shoes, weather-appropriate clothing, and a rain jacket, as Olean has varying temperatures and occasional showers year-round. If you plan to hike, bring outdoor gear and sun protection.

  • What is the nightlife in Olean like?

    Olean has a laid-back nightlife scene, with neighborhood taverns, casual bars, and venues hosting live music or trivia nights. Local restaurants often feature relaxed atmospheres for gathering with friends or family.

  • What are the most popular events or festivals in Olean?

    Olean hosts seasonal festivals, including holiday parades, summer arts events, and community celebrations centered around food and music. The Strawberry Festival and Santa Claus Lane Parade are frequently mentioned annual highlights.

  • Are there family friendly vacation rentals in Olean?

    Olean has a range of family friendly vacation rentals, including whole homes, apartments, and guest suites. Many properties include extra amenities and location advantages for guests traveling with children.

Quick stats about vacation rentals in Olean

  • Total vacation rentals

    Explore 50 vacation rentals in Olean

  • Nightly prices starting at

    Olean vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,110 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Olean vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Olean rentals

  • 4.9 Average rating

    Olean stays are highly rated by guests—averaging 4.9 out of 5!

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