Family-friendly vacation rentals in Olean

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.

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Entire Chalet! Hot Tub! Vaulted Timber Ceiling! AC

Nestled 8 minutes from Ellicottville, this 4-bedroom, 4-bath chalet is a 3,600 sq. ft. retreat on 5.7 acres. Relax on the wraparound deck with stunning views, fish in the bass-filled pond, or enjoy an outdoor fire pond side . Inside stay cozy and relaxed while you enjoy a timber-vaulted great room, two stone gas fireplaces, a full kitchen, central air, propane heat, and a hot tub. With luxurious amenities and serene surroundings, it’s the perfect escape for unforgettable memories. Book now in !

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.

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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!

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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.

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

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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.

The Buzzy Bee

Escape to the Buzzy Bee, a charming vintage camper nestled in the heart of our 50-acre farm. Wake up to breathtaking sunrises, enjoy peaceful sunsets over the pastures and watch horses, donkeys, cows, ducks and other farm animals just steps away. Sleeping up to 6 guests with 4 beds. The Bee is perfect for families, coupes or friends seeking a unique farm stay experience. End your day stargazing by the campfire and enjoying the quiet beauty of country life.

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Pines Chalet in Ellicottville ~ Hot Tub~Fireplace

Located just two miles from the Village of Ellicottville, The Pines on Maples offers stunning views & a variety of amenities for relaxation and entertainment. Tucked away in the rolling hills of Western New York, this chalet features a large wood deck with a Weber grill & sitting area, as well as a walk-down path to an eight-person hot tub & an unilock fire pit with Adirondack chairs. State of the art Stuv indoor fireplace for cozy cabin days!!

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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!!

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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.

Spring Vacation* Fire Pit, Grill, Hiking

This beautiful lodge in the woods is the perfect get-away for families and groups wanting privacy. Yet, it's only 25 minutes to Holiday Valley for year-round activities and dining! Located at the end of a dead-end road, we have 2 ponds and woods for hiking. Kids and big kids love swimming, hiking and the fire pit at night! Adults love the upper deck off the bar, overlooking the pond!