Family-friendly vacation 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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Guest favorite

Tiny home in Machias

4.86 out of 5 average rating, 389 reviews

Lucky Day Cabin Ellicottville/Ashford 30 acres

Family built cabin on 30 acre country estate, just outside exciting year round resort village of Ellicottville. Perfect for nature lovers and outdoor enthusiasts, the cabin has all necessities, similar to a tiny house. Nestled near the gardens, and surrounded by quiet rolling hills. Enjoy with door step delivered breakfast, or book a guided hike with estate owner and learn about medicinal plants and flowers, the topography of the land and a farm fresh picnic lunch on the peninsula of our lake.

Guest favorite

Home in Shinglehouse

4.88 out of 5 average rating, 113 reviews

Shinglehouse. Pa. 3bdrm stargaze nr Cherry Springs

This home is very clean&extremely cozy. Very comfee beds Starlink wifi Excellent reception on all devices. 17.5 download and 4.73 upload .The small town feel with Diners,Drive in movies, fairs or visit Niagara Falls.Skiing in Ellicottville est. 45 minutes away & in the summer try their rope course, coaster ride and zip line. In the town of Olean go to a St. Bonaventure basketball game, bowling& 30 minutes away at a sports plex. Stargaze at Cherry Hill Park or back yard. Dogs allowed 35p. nt

Superhost

Home in Ellicottville

4.71 out of 5 average rating, 125 reviews

Charming Village Retreat with Hot Tub!

Welcome to your cozy retreat in the heart of Ellicottville, the ultimate destination for fun! Featuring a hot tub, our charming 3-bedroom, 2-bathroom house offers the perfect blend of modern comforts situated just a stone's throw away from the vibrant village center. This is the ideal base for your adventures. The house has been lovingly restored with a back deck, hot tub, gas BBQ, and a fully stocked kitchen. A flat-screen TV with ROKU. This is a legal, licensed rental RENTAL2020-00002

Superhost

Home in Ellicottville

4.86 out of 5 average rating, 185 reviews

Ashford Villa near Ellicottville

Privacy & Grandeur awaits you at this 4,000 sq. ft. Villa located on a 10 acre estate close to Ellicottville (12 min) & Holiday Valley (15 min). It sleeps 14 (16 with air mattress): 1 king, 3 queen, 2 single & two bunk bed sets & 2 Pack n Plays. Also, four full bathrooms ensures there is no wait! Finally, a 2 car garage and a huge basement. It is a great meeting place for big groups such as family gatherings, re-union of friends, etc. Make memories with the people you cherish most!

Guest favorite

Cottage in Olean

4.82 out of 5 average rating, 179 reviews

Artists cottage - mid century

View birds, wildlife in an old forest along the Allegany River from the porch, deck or large picture windows. Relax, renew, read a book, create, write, paint, unplug. (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). There are many unique and cleaver features. Family mementos through history are on display.

Superhost

Chalet in Swain

4.88 out of 5 average rating, 386 reviews

Chalet at Swain ski resort, 50% off- Letchworth

Visiting Swain ski Mountain Resort is truly a wonderful experience. This open space with private lodge like feeling is fantastic for a romantic getaway or for a vacation with family and friends. Immerse yourself in the beauty of the outdoors within the exquisite state land of upstate New York. Just 15 miles from Letchworth State Park. 12 miles from Stony Brook State park. Rattle Snake State Park is just a block away. If you love adventure and the outdoors this is the perfect place!

Superhost

Condo in Ellicottville

4.82 out of 5 average rating, 139 reviews

The Great Escape Wildflower 4 Seasons Sleek Condo

Whether Summer/winter this fully renovated condo is the place to stay. Equipped with air conditioner for those hot summer days after a round of golf/day at the pools. Shuttle to HV. Ground floor unit w/2 bedrooms, 1 bath w/a scenic patio off master and living room. Lg Master bedroom w/king bed 2nd bedroom has T/D bunk w/D futon. Both equipped with TV. Spacious Living room w/pullout, sectional, tv patio doors and a fireplace to sit back relax and enjoy!

Guest favorite

Home in Ellicottville

4.96 out of 5 average rating, 150 reviews

Stay in style. Walk to everything!

Sure to be your favorite for visits to come! Enjoy this beautiful home with large kitchen, nice & comfortable furniture, and newer carpet throughout. Relax on the back deck or front porch. Off-street parking. WiFi. Go head-to-head on our air hockey or shuffleboard tables. Take a short walk to the heart of town! Perfect for time with spa weekends, golf outings, ski season, family, and more. Available for long-term rentals.

Guest favorite

Cabin in Dalton

4.97 out of 5 average rating, 136 reviews

Upscale Cozy Cabin in the Woods-LETCHWORTH

20 MINUTES FROM LETCHWORTH STATE PARK. WiFi - High-Speed Internet -No Pets (Team member is allergic to animals) -No Smoking -No shoes worn inside cabin -No cutting down live or dead trees -No use of WOOD BURNING STOVE -No parties, events of any kind, and additional guests other than those listed in your reservation are not permitted without our prior approval. Check In: 3PM Check Out: 11AM

Guest favorite

Rental unit in Great Valley

4.88 out of 5 average rating, 250 reviews

Cozy apartment tucked into the forest (with sauna)

Nestled in the forest only seven minutes’ drive from Holiday Valley, this contemporary style self-contained apartment is the perfect weekend getaway for skiing and nature-loving couples. With every luxury and convenience including a sauna, you can home cook meals or barbecue on the deck, with nothing but forest beyond, relax and watch a movie on our LCD screen or use high speed Starlink internet.

Guest favorite

Cottage in Franklinville

4.98 out of 5 average rating, 185 reviews

Countryside Zen Cottage with remarkable views

Spend a weekend, week or more in this fully furnished, dog friendly, 2 BR with loft country retreat near Rushford Lake, NY. Views, sounds and fresh air of the countryside will facilitate deep relaxation and re-energize. Surround yourself with nature, watch from your second story deck as deer feed in the fields, wild turkey gather and ducks frolic in the pond. This is true country living.

Guest favorite

Cabin in Coudersport

4.88 out of 5 average rating, 151 reviews

Log Cabin Stream Firepit 1g Wi-Fi Cherry Springs

A Cabin By The Stream for Star Gazing. Streamside Firepit. 1Gig Internet. Your private Stream side Log Cabin lodging for star gazing at nearby Cherry Springs State Park.. Need an Astronomer for a private guided star tour? we'll give you our recommendations. We can point you in the best direction. Spend the afternoon at Rainbow Paradise Trout Farm. Check out The Pa Grand Canyon, The Kinzua