Family-friendly holiday 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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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.
Guest house in Olean
4.86 out of 5 average rating, 184 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 cabin is nestled among tall pine trees, showcasing a rustic wooden exterior and a welcoming porch. The surrounding landscape reveals vibrant autumn foliage in hues of orange and red, creating a serene and secluded atmosphere.
Cabin in Ellicottville
4.95 out of 5 average rating, 144 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.

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.
Apartment in Ellicottville
4.95 out of 5 average rating, 375 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
Cabin in Coudersport
4.94 out of 5 average rating, 140 reviews

Potter County Family Retreat-Dark Sky Stargazing

Our fun hidden gem is just the retreat you need! Only 7 minutes from Downtown Coudersport for all your shopping and dining needs. 20 miles from Cherry Springs Star Gazing. Very close proximity to ATV trails/Pilot Program in season. Our retreat is part of an old 100 acre farm that has 3 ponds you can fish in, hiking trails and woods that you are more than welcome to explore. You will enjoy star gazing from the view of the front yard! An OFFSITE cabin to our Potter County Family Campground.

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, 170 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
A newly constructed cabin is nestled among green trees and vibrant foliage. The orange exterior is complemented by a sloped roof. Surrounding the cabin are diverse plants, indicating a naturally rich landscape. The setting offers a sense of seclusion and a connection with nature.
Cabin in Rushford
4.88 out of 5 average rating, 206 reviews

A tranquil cabin with a nice view on 90 acres.>

A semi remote, off the grid, newly constructed,comfortable 14' x 24' cabin with a 8' x 14' porch. Solar powered with running hot water and heat. Located on 90 acres of recreational and hunting land. The electricity is sourced from an on-site solar system, with a remote start generator to assure never losing power. This location is for those who are looking for an experience different from the hotel/motel setting. However, still providing all basic amenities Hunting is available.

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.

Popular amenities for Olean family-friendly rentals

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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 £45 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

  • Wifi availability

    20 of Olean holiday rentals include wifi 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