Family-friendly holiday rentals in Olean

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.

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!

We had a wonderful time at Blue Skies Lodge! They put so much effort into every little detail, the place really is amazing. The star gazing field is beautiful and the trails were so nice to explore! Their hot tub is top tier and very clean. The entire place was cleaned well. Such a charming getaway, we’ll be back for sure!

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!

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.

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.

Frances's place was amazing! We felt right at home with everything we needed (extra towels, wine glasses, ice trays, etc.). Couldn't have asked for a better location with downtown just a 5 minute walk away and both ski hills nearby too. Would definitely recommend this home!

Such a great comfortable location!

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.

We had a very enjoyable stay and enjoyed the friendly greeting from the Aussie’s. We would like to stay here again!

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!

This was my second stay at Andrea's place. Check-in is easy. Linens and towels are provided. The house is located in a quiet neighborhood with ample parking. It's a plus that the property is dog-friendly and it's easy to take walks around the neighborhood.

Alexander's home was an amazing spot for us to enjoy the slopes at holiday valley. The living space was perfect for my family to unwind after a day skiing and it was perfectly located close to the hills and quaint Ellicottville town but still private. The rooms were spacious and all the amenities were perfect! We will definitely be coming back next year!

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!

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.

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.

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.

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!

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!

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 !