Family-friendly holiday rentals in Olean

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Top-rated family-friendly rentals in Olean

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Superhost
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
4.86 out of 5 average rating, 185 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.

Top Guest favourite
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, 376 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 favourite
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, 156 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
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, 168 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
The cottage exterior features a stone façade, complemented by a welcoming porch and large windows. Greenery surrounds the entrance, with potted plants adding a touch of life. The front door, framed by glass panels, offers a glimpse into the cozy interior.
Cottage in Olean
4.83 out of 5 average rating, 191 reviews

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.

Top Guest favourite
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, 171 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.

Top Guest favourite
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, 257 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 favourite
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, 209 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 favourite
Cabin in Shinglehouse
4.96 out of 5 average rating, 216 reviews

Cozy Cabin with a Vista - 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.

Top Guest favourite
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, 336 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

Top Guest favourite
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
4.93 out of 5 average rating, 418 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.

Top Guest favourite
The interior space is showcased from an elevated viewpoint, revealing a cozy seating area with a sofa and a patterned rug. The kitchen area features white cabinetry, and natural light is filtered through light-colored curtains. A staircase leads to an upper sleeping area.
Tiny home in Ellicottville
4.93 out of 5 average rating, 393 reviews

Tiny House in the heart of Ellicottville

5 1/2 Park Square is an adorable tiny house property located in the heart of Ellicottville. It is walking distance to restaurants and bars. Holiday Valley Ski Resort and Holimont within 2 minute drive. Hiking trails abound. Summer and Fall Seasons provide a fantastic weekend adventure! *as featured in StepOutBuffalo as a must rent Tiny Space!

Popular amenities for Olean family-friendly rentals

When is the best time to visit Olean?

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Avg. price$242 NZD$232 NZD$244 NZD$230 NZD$271 NZD$222 NZD$263 NZD$251 NZD$239 NZD$248 NZD$256 NZD$217 NZD
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Quick stats about holiday rentals that are family-friendly in Olean

  • Total holiday rentals

    Explore 20 holiday rentals in Olean

  • Nightly prices starting at

    Olean holiday rentals start at $102 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,170 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Olean holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Olean rentals

  • 4.7 Average rating

    Olean stays receive an average rating of 4.7 out of 5 from guests