Family-friendly holiday 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

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.
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 favourite
Cabin in Austin
4.91 out of 5 average rating, 68 reviews

Hot Tub in the Forest Stargazing Field Remote Cabi

CatherineRating, 5 stars1 month 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.
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

Guest favourite
Cabin in Galeton
4.89 out of 5 average rating, 169 reviews

*Dry Camp visit Cherry Springs Dark Skies

JenRating, 5 stars6 months ago
This was our second stay at William’s place. We love it here! Great little cabin that has everything we need. The location is so peaceful and perfect for relaxation and star gazing.
Guest favourite
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
Cottage in Austin
4.94 out of 5 average rating, 206 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 favourite
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 favourite
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!
Top guest favourite
Home in Alfred
4.97 out of 5 average rating, 349 reviews

Perfect choice for Alfred Univ./A. State visitors!

DeniseRating, 5 stars3 months ago
Perfection! Will be back!
Guest favourite
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!!!!
Guest favourite
Cabin in Rexville
4.95 out of 5 average rating, 334 reviews

Crows Nest, Pet-friendly, Private, Wooded Retreat

JulieRating, 5 stars1 week ago
This is was our 3rd or 4th time back to the crows next. As usual it did not disappoint! Our weekend was full of family time around the camp fire , fishing in the pond and hiking through the woods. We never want to leave when it’s time to check out. We will be back again!

Family-friendly home rentals with wifi

Guest favourite
Flat 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 favourite
Apartment 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.
Superhost
Guest house 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 favourite
Cabin in Great Valley
4.91 out of 5 average rating, 309 reviews

The Porcupine, featuring fiber optic internet

WilliamRating, 5 stars1 month ago
What a neat little area this is, and this cabin is a gem. We'll be back. There's a small waterfall running around the cabin, the sound of water is peaceful and it is a quiet road
Guest favourite
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.
Superhost
Home in Canaseraga
4.91 out of 5 average rating, 265 reviews

Farmhouse at Brookdale Farms- a private, refuge

DanielRating, 5 stars6 months ago
The quaint farmhouse is the perfect getaway to enjoy, explore this very scenic area.
Guest favourite
Home in Canaseraga
4.92 out of 5 average rating, 60 reviews

Country Gentlemens 220 Acre Estate

GaetanoRating, 5 stars6 months ago
We recently stayed at this rental and had an amazing experience. The atmosphere was peaceful and welcoming, perfect for relaxing and unwinding. The spacious layout provided plenty of room for our family to spread out, and we never felt cramped. Whether it was enjoying meals together or just lounging around, the space was ideal for quality family time. The surrounding area also contributed to the calm vibe, adding to the overall sense of peace. We would highly recommend this rental to anyone looking for a great place to stay with their family! Thank you David for sharing your amazing home.
Home in Ellicottville
4.92 out of 5 average rating, 142 reviews

EVL Acres - 13 acres & 3 minutes to village!

SergeyRating, 5 stars1 month 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!

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

  • Total rentals

    20 properties

  • Nightly prices starting at

    ÂŁ45 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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