Family-friendly vacation rentals in Olean

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Olean family-friendly rentals

Family-friendly home rentals with a hot tub

A two-story chalet is surrounded by trees and vibrant foliage, showcasing a dark wooden exterior and a spacious balcony. The front yard is dotted with green shrubs and a stone pathway leading to the house. A grill is visible on the lower deck.
Chalet in Ellicottville
4 out of 5 average rating, 16 reviews

Mountain Watch

NicholasRating, 5 stars28 months ago
We had an absolutely wonderful time. The property was excellent and the amenities were spot on. It is a very charming and comfortable home. The location is perfect, can walk across the street to the lodge and lifts. I will booking again next year.
A spacious white two-story house features a brick chimney and a well-maintained front yard. Surrounding greenery enhances its appeal, and large windows provide ample natural light. The driveway is visible in front, leading up to the welcoming entrance.
Home in Little Valley
4.8 out of 5 average rating, 55 reviews

Holiday Valley-Sleeps 19. HotTub,Game Room,etc

EmilyRating, 5 stars14 months ago
This place was great! Accommodated a large group not only with beds, but also seating in the TV room and around the dining room table. Mark was so easy to communicate with. He always responded right away. All of the listing information and pre-check in instructions were straightforward and easy to follow. Will stay again!
Guest favorite
A private hot tub is situated on a deck, surrounded by lush greenery. The bubbling water is visible, and the deck is made of wooden planks, creating a natural and relaxing atmosphere amid the forest.
Cabin in Austin
4.91 out of 5 average rating, 68 reviews

Hot Tub in the Forest Stargazing Field Remote Cabi

CatherineRating, 5 stars2 months ago
This is a lovely place to stay. It feels cozy and homey, and I love the dedication to the decorative theme. The stargazing field is very special. If you are heading to this area to stargaze, this is the place.
A colorful game of Connect Four is displayed against the wall, adding an element of fun to the room. A wooden fireplace with a protective screen stands nearby, with soft light visible from the fire. Neutral walls and warm wood accents create a cozy environment.
Chalet in Ellicottville
4.81 out of 5 average rating, 32 reviews

Ellicottville Ski Chalet

StacyRating, 5 stars3 months ago
Jacqueline and Ella’s wooden chalet is such a cozy and charming home to stay for a group looking to reconnect. The massive couches, toasty fireplaces, wood bar, long dining table, and bubbly hot tub are fantastic places to come together to share stories and memories. Bedrooms have space and storage for luggage, and the downstairs single bed is a Full size (upstairs has a kids twin). Main floor bathroom has a large shower and upper floor has a massive tub. Plenty of supplies, including towels, hair dryer, shampoo/conditioner/bodywash, kitchen supplies, cocktail/wine supplies, coffee, detergent, and tons of games. TVs are HD and big enough for the whole crew to watch the Bills game 🦬. We were able to fit 2 sedans and an SUV in the parking area (just don’t block the garage). Missing anything or need a bit of maintenance on older parts of the home? Jacqueline is the most responsive host I’ve had and will get it taken care of. Thanks for the stay!

Family- and pet-friendly home rentals

A serene snowy landscape is captured, featuring a blanket of untouched snow covering the ground. Sunlight filters through bare trees, casting long shadows on the snow. A distant structure is partially visible, adding to the tranquil winter scene.
Apartment in Ellicottville
4.8 out of 5 average rating, 90 reviews

EVL 2 BR Cozy APT w/ Retro Cabin feel on 7 acres

CoreyRating, 5 stars2 months ago
Great little duplex home. Originally booked the lower half but things happened out of control and Brian upgraded us to the much nicer upper apartment. Cozy, clean, close to town and the mountain. 10/10 will stay here again.
Guest favorite
An outdoor play area features a swing set, a colorful slide, and a spinning merry-go-round, set on a lush, green lawn. Nearby, two small chairs in bright colors are positioned for relaxation, surrounded by trees and an open field in the background.
Home in Shinglehouse
4.88 out of 5 average rating, 113 reviews

Shinglehouse. Pa. 3bdrm stargaze nr Cherry Springs

JohnRating, 5 stars8 months ago
Nice place to stay. Beautiful view of rolling hills out living room window.. Home was clean and comfortable. Debbie was very responsive. Would stay there again.
Guest favorite
A wooden porch framed by rustic planks is covered in a light layer of snow. A corgi peacefully rests at the entrance, with snow blanketing the ground and the building’s exterior visible in muted tones. Several windows are positioned to offer natural light.
Guest suite in Salamanca
4.84 out of 5 average rating, 94 reviews

The Stable at The Crosspatch

CodyRating, 5 stars2 months ago
Such a great comfortable location!
Superhost
A snow-covered farmhouse is set against a cloudy sky, featuring a welcoming porch with chairs. The white landscape creates a serene ambiance, contrasting with the rustic charm of the gray siding and warm wood accents.
Cottage in Austin
4.94 out of 5 average rating, 207 reviews

Katie's Cozy Cottage

DonaldRating, 5 stars4 months ago
Great house on a peacful farm, with lots of room to walk the dogs. Close to Elk National Forest and a short drive to Emporium for supplies. Katie is very responsive and helpful, she made sure we had everything we needed in the house and loaned us something that we had forgot. This is a great location for a Potter County getaway, we hope to stay here again one day.
Guest favorite
A charming log chalet is blanketed in fresh snow, with warm light glowing from the windows. A decorated evergreen tree stands nearby, complementing the winter scenery. The surrounding landscape features rolling hills, quietly adding to the tranquil atmosphere.
Chalet in Ellicottville
4.98 out of 5 average rating, 65 reviews

Escape - Log Style Cozy Ski Chalet - Pets Welcome

RuthRating, 5 stars2 months ago
We loved this place. It worked out so well for my family. It snowed every day, so the skiing was great. The chalet has a level driveway and easy access to the village and slopes. (no steep slippery roads!) It was clean, warm, and cozy with comfortable beds. We hope to return next year.
Guest favorite
A wooden deck extends from the cabin, featuring a picnic table and benches. Nearby, a swing set is visible in the grassy yard, alongside a greenhouse. The surrounding landscape consists of gently rolling fields under a bright sky.
Tiny home in Machias
4.86 out of 5 average rating, 407 reviews

Lucky Day Cabin Ellicottville/Ashford 30 acres

JeremyRating, 5 stars1 month ago
We had a very enjoyable stay and enjoyed the friendly greeting from the Aussie’s. We would like to stay here again!
Guest favorite
The handcrafted log cabin features a spacious wraparound deck supported by sturdy posts and adorned with a wood railing. The stone chimney rises from the side of the building, while a satellite dish is mounted on the front. The natural landscape provides a serene backdrop.
Cabin in Austin
4.96 out of 5 average rating, 97 reviews

Bear Trail Lodge

DavidRating, 5 stars1 month ago
Sam's house was amazing. It was very spacious. The kitchen had every amenity I could imagine and more. The bed I slept in was very comfortable. We sat on the LARGE wraparound deck and listened to the creek far below. In three hours, we only saw two cars. So peaceful! We've been to Cherry Springs State Park (ten miles away) to see the amazing stars. We are sure that without a full moon and some wispy clouds, the view would have just as good. When it rained, six of us comfortably hung out all afternoon in the great room with cathedral ceilings. It was so close to two maple sugarhouses we visited. In mid-spring, full summer, a colorful fall, and in deep snow, this house would be a perfect! It comfortably sleeps ten adults. With outdoor dining, ten adults works. The kitchen table handles six; ten would be a stretch. The bedrooms were spread out and with 3.5 bathrooms, ten adults would be easy!!! Well worth the cost! Same quickly answers emails. Perfect host!!!! Perfect house!!!!
The kitchen features wooden cabinets, a refrigerator, and a gas stove. A countertop offers ample space for food preparation. Natural light enters through large windows adorned with patterned curtain valances, and a small rug adds a touch of color to the floor.
Home in Ellicottville
4.92 out of 5 average rating, 142 reviews

EVL Acres - 13 acres & 3 minutes to village!

SergeyRating, 5 stars2 months ago
We booked Chris' location based on the ratings and because we knew the area we wanted to stay in. By chance, the house was available for the dates we were interested in, as it was pretty booked on other days. Chris was very helpful, promptly answering our calls and assisting whenever needed. Realistically, we had no issues, but knowing we had a responsive and accommodating host was reassuring. The house closely matched the description. It’s a great place to stay for a few days if you’re looking to explore the area, go skiing, hiking, or enjoy other activities. While not brand new, it was clean, functional, and everything (water, heating, etc.) worked as expected—no issues at all. Overall, we were very satisfied with our stay. The price was very fair, and a 5-star rating is well deserved!

Family-friendly home rentals with Wifi

Guest favorite
A gravel driveway leads up to a garage apartment situated behind a two-story house. Flower beds with vibrant plants line the path, while a lush green lawn extends on either side. Tall trees provide a natural backdrop, completing the serene outdoor setting.
Apartment in Machias
4.92 out of 5 average rating, 132 reviews

Lime Lake 3 bedroom getaway

JillRating, 5 stars3 weeks ago
I stayed at Robins place with friends so we could hike the FLT Conservation Trail. The location was perfect, quiet and cozy for weary hikers. Robin and her husband greeted us when we arrived and were super friendly!
Guest favorite
A winter landscape is showcased, featuring a frozen pond surrounded by a blanket of snow. Trees stand bare against a blue sky, and snow-covered buildings are visible in the distance, creating a peaceful, serene atmosphere.
Condo in Ellicottville
4.77 out of 5 average rating, 74 reviews

Wildflower 48 - Pond View Ellicottville New York

CaseyRating, 5 stars2 months ago
This is my third stay in Stephan and Sylvie’s Airbnb. They are great hosts. Quick to reply and always making sure that the client is satisfied. I have visited Ellicottville every year since 2019, and have stayed in various Wildflower condo units. While other hosts and units were good, I keep going back to Stephan and Sylvie’s place. I don’t give out recommendations lightly, but I think that if you try their place you will find value and a responsive host.
A cozy living space features a stone fireplace with a warm glow. A comfortable sofa is positioned near a wooden coffee table, and a television is mounted on a wall opposite the fireplace. Natural light enters through large windows, illuminating the rustic decor.
Townhouse in Ellicottville
4.84 out of 5 average rating, 94 reviews

Walk to weddings, concerts, mountian fun. Air/con

RichardRating, 5 stars2 months ago
When visiting Holiday Valley for some skiing this ski-in, ski-out accommodation is absolutely perfect! Our group has been staying here for a view years and the place never disappoints. The kitchen is well stocked and the living space is very comfortable. Looking forward to our next opportunity to stay here.
The exterior of the home features a two-story structure with a balcony and large windows, surrounded by greenery. Stacked firewood is visible beneath the balcony, and a colorful outdoor area can be seen on the ground level.
Home in Ellicottville
4.81 out of 5 average rating, 54 reviews

Ski House - Sleeps up to 9

LoganRating, 5 stars2 months ago
Michelle was very responsive and approachable well before checking in. We had a last minute group Ski trip and Michelle’s place was the perfect option to accommodate us. I recommend this property to any small group or family, definitely great for two couples.
Guest favorite
A rustic dining area features a wooden table surrounded by six chairs. The open kitchen is visible in the background, containing modern appliances, cabinetry, and ample counter space. A cozy seating area with a brown sofa is located to the right, enhancing the welcoming environment.
Guesthouse in Great Valley
4.76 out of 5 average rating, 144 reviews

Great Valley/Ellicottville Ski,Bike,Golf,LoveLife

DougRating, 5 stars3 months ago
I truly loved this place! My dad, son and I had the best time staying here and skiing at Holiday Valley. It was clean, warm, comfortable and has some of the best ski memorabilia on the walls. Really a very cool place. To be clear, this place is not fancy, but I was not expecting anything fancy. I wanted a safe place that was warm and inviting, away from the busy, hectic Ellicotville and this nailed it. I would definitely stay here again. Overall this was the perfect place for my trip!
Guest favorite
A cozy living area is highlighted by a stone fireplace, providing a warm focal point. A dark sofa sits opposite a dresser, while a soft area rug with a subtle pattern adds texture. Floor-to-ceiling curtains frame a window, accentuating the space.
Home in Ellicottville
4.95 out of 5 average rating, 75 reviews

Perfect place to stay - Ellicottville

LisaRating, 5 stars3 months ago
This home was absolutely perfect for our weekend getaway! The location was fantastic, right in the heart of Ellicottville with easy access to everything we wanted to see. The space itself was spotless, beautifully decorated, and had everything we needed for a comfortable stay. Mike was incredibly responsive and helpful. We would definitely stay here again!
A modern blue exterior of the vacation home is enhanced by a wooden deck with railings. Multiple windows allow for natural light, while a landscaped area with small shrubs contributes to the inviting entrance. The surrounding green lawn adds to the overall appeal.
Home in Ellicottville
4.96 out of 5 average rating, 28 reviews

Ellicottville Vacation Rental

JacquelineRating, 5 stars3 months ago
We so enjoyed our stay at this lovely home . The house was spotless and very accommodating for our needs . The beds were great and the living room area warm and comfortable. The kitchen area is huge and plenty of seating at the table / counter space . The area was close enough to slopes and town . Beautiful view from back windows . Joseph , the host, is the best by far we have encountered. He is friendly, communicative and we appreciated his flexibility for us . We look very much forward to returning to Joseph’s home ! Thank you !
Superhost
The two-story house features a classic design with a white exterior and a spacious front porch supported by four columns. Lush greenery surrounds the property, enhancing its inviting presence. Nearby structures can be glimpsed, showcasing the historic neighborhood.
Home in Springville
4.86 out of 5 average rating, 96 reviews

1887 Parsonage - part of Springville Arts Center

HollyRating, 5 stars5 months ago
Springville is the best kept secret in western NY! Beautiful town full of genuine people. Seth went above and beyond to ensure our stay exceeded our expectations. I highly recommend “Open Farms” goat rescue on Genesee Rd. An amazing farm with a mission to serve everyone!

Quick stats about vacation rentals that are family-friendly in Olean

  • Total rentals

    20 properties

  • Nightly prices starting at

    $60 before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore

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  4. Cattaraugus County
  5. Olean
  6. Family-friendly rentals