Family-friendly vacation rentals in Olean

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Top-rated family-friendly rentals in Olean

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious studio is furnished with a queen-size bed adorned with decorative pillows and a comfortable couch. Natural light filters in through windows, illuminating the dart board and foozeball table. A bathroom door is visible at the back, contributing to an open and inviting atmosphere.

Guesthouse 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 favorite

A comfortable living area features a sofa positioned across from a gas fireplace. A large television is mounted above a wooden shelf, creating a functional space. Natural light flows in through sliding glass doors that open to a grassy outdoor area.

Condo 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 favorite

A welcoming wooden sign reading 'WILDFLOWER' is prominently displayed at the entrance, framed by well-maintained greenery and colorful landscaping. The stone base adds an earthy texture, while nearby trees are dotted with budding branches, suggesting a peaceful environment.

Condo in Ellicottville

4.95 out of 5 average rating, 343 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

A spacious living area is highlighted by green walls and natural light filtering through two windows. A stone fireplace serves as a focal point, with a television mounted above. Comfortable seating includes a dark sectional sofa and a leather armchair. A wooden coffee table occupies the center.

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!

Guest favorite

A cozy living room features a gas fireplace set into a stone wall, complemented by a comfortable leather sofa and a green armchair. A large window offers natural light and views of the outdoors. Wall art and a wooden shelf with decorative items add a personal touch.

Condo in Ellicottville

4.91 out of 5 average rating, 266 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 favorite

A spacious living area features a comfortable couch and armchair arranged around a coffee table. A stone fireplace anchors one wall, while a dining table is positioned nearby. The kitchen area, visible in the background, is equipped with modern appliances and wooden cabinetry.

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

Superhost

The living room features a comfortable blue sofa with decorative pillows, a wooden coffee table, and a gas fireplace. Large windows allow natural light to fill the space, with a view of the outdoors. A flat-screen TV is mounted on the wall across from the seating area.

Townhouse in Ellicottville

4.82 out of 5 average rating, 153 reviews

★ SKIING, HIKING, VILLAGE OF EVILLE MTN ESCAPE ★

Snugly nestled at the foot of the Ellicottville mountains, this Wildflower townhome provides easy access to skiing (across the street from Holiday Valley), hiking, fishing, golf and a whole host of nature activities. With the village of Ellicottville only a 15-20 minute walk (or very short drive) away, the nearby comforts of civilization include plentiful shops, restaurants and other attractions. You can't beat this location if you are looking for a relaxing retreat from the hustle and bustle.

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, 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 favorite

A two-story country home is depicted, featuring blue siding and a welcoming porch. Surrounding greenery and trees frame the property, with a backdrop of colorful autumn foliage. The gravel driveway and well-maintained lawn create an inviting outdoor space, enhancing the peaceful rural setting.

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 favorite

A spacious living area features vaulted ceilings and hardwood floors. Two comfortable armchairs are placed beside a wooden coffee table, which is centered on a soft area rug. A modern kitchen is visible in the background, equipped with stainless steel appliances and a dining table.

Apartment 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.

Top guest favorite

A charming cabin with a wooden exterior is set against a green lawn. The structure features multiple windows, allowing natural light to enter. A small staircase leads to the entrance, while a fenced yard surrounds the property, offering a sense of privacy and space.

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!!

Top guest favorite

A modern cabin with a green metal roof is situated on a gently sloping lot, surrounded by bare trees. A well-maintained porch with white railings extends across the front, featuring an American flag displayed proudly. Steps lead up to the entryway.

Cabin in Shinglehouse

4.96 out of 5 average rating, 212 reviews

Cozy Cabin with a View - 500 Private Acres

Modern Cabin sitting on 500 private acres. We have private trails, fishing, and hiking available to all guests. Features 2 bedrooms with 4 twin beds, full kitchen, WiFi, DirecTV, gas fireplace, AC, sauna, and 1 full bath. Our cabin also has a large loft area with a futon and 4 twin beds. Comfortably sleeps between six and eight guests with air conditioning and heating. Kitchen stocked with cooking essentials.