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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Top 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

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.

Superhost

The cottage exterior features a stone façade, complemented by a welcoming porch and large windows. Greenery surrounds the entrance, with potted plants adding a touch of life. The front door, framed by glass panels, offers a glimpse into the cozy interior.

Cottage in Olean

4.83 out of 5 average rating, 183 reviews

Artists cottage - mid century

The perfect spot to relax, read, write meditate. View birds, wildlife in an old forest along the Allegany River from the porch, deck or large picture windows. Take a walk. (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)1956. There are many unique and cleaver features. Family mementos through history are on display.

Guest favorite

A welcoming living area is presented with hardwood flooring and a cozy wood fireplace. A large television is mounted above a brick mantel, while comfortable seating, including a recliner, frames the space. Warm colors and decorative touches create a relaxed atmosphere.

Home in Ellicottville

4.87 out of 5 average rating, 193 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!

Superhost

A warm living space features a stone fireplace with a flickering fire. A bottle of red wine rests on a wooden table, accompanied by two wine glasses. Nearby, a festive candle is set atop a decorative tray, contributing to a cozy atmosphere.

Chalet in Swain

4.88 out of 5 average rating, 403 reviews

Chalet- Letchworth and Stony Brook State Parks 50%

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!

Guest favorite

The living area features wooden walls and flooring, creating a rustic ambiance. A comfortable seating arrangement includes a sofa and chairs. A wooden table sits nearby. A staircase leads to the upper level. Wall-mounted decorations enhance the natural theme, including mounted animal displays.

Cabin in Almond

4.95 out of 5 average rating, 291 reviews

The Country Cabin

Quiet, peaceful, and private cabin in the woods. Explore 4000 acres of State Land nearby. Hiking, nature walks, or birdwatching. Enjoy cross-country skiing on the nearby state land. Relax by the pond, fish, or take a refreshing swim. Tall Pines ATV Park (11 miles) offers off-road adventures. Hit the slopes at Swain Ski Resort (22 miles) for winter sports. Located near SUNY Alfred and AU (2 Miles), ideal for parents visiting. Perfect for a family vacation or a weekend getaway.

Top guest favorite

Home in Ellicottville

4.97 out of 5 average rating, 105 reviews

Windsor Castle - Cozy Farmhouse Ellicottville

Windsor Castle - Your Cozy Ski & Golf Retreat Escape to serenity at Windsor Castle, a charming 2,300 sq ft farmhouse nestled on four rolling acres in Ellicottville. This beautifully restored 1900s home perfectly blends rustic charm with modern comfort, featuring a tranquil 3/4-acre pond that mirrors the changing seasons. Minutes from Western New York's premier ski destinations and golf courses, this private retreat offers the perfect balance of seclusion and accessibility.

Guest favorite

A welcoming living room is featured with two comfortable sofas positioned around a rustic wooden coffee table. A stone fireplace adds warmth to the space, complemented by a flat-screen TV mounted above. Large curtains frame the door leading to the balcony, allowing natural light to filter in.

Townhouse in Ellicottville

4.94 out of 5 average rating, 153 reviews

Alpine Retreat- Bottom of ski hill, gorgeous view

Slope-side bliss awaits at this townhouse near Sunrise lift. Just a 4-min drive or 15-min walk to a vibrant town with shops, dining, and events. Pet/smoke-free, it offers high-speed WiFi, Roku TV, a cozy fireplace, AC, and new washer/dryer. The deck boasts Muskoka chairs and scenic views. Your perfect mountain escape! You'll love the vibe and access to the hill and golf course. We're a Super-Host and aim to provide exceptional value.

Guest favorite

The living area features a light-toned sofa and armchair, complemented by decorative cushions. A wooden coffee table sits in front of the seating, with a small potted plant atop it. Large windows provide natural light, while a dining area with a dark wooden table is visible in the background.

Apartment in Ellicottville

4.81 out of 5 average rating, 113 reviews

Apartment with AC, close to Ellicottville village

Beautiful, modern 2 bedroom/1 bathroom apartment perfect for a getaway with friends or a fun family weekend! **25% off for WEEKLY bookings** Equipped with all of the amenities of home including linens, kitchen wares, gas fireplace, washer and dryer and a TV in each room. Pull-out couch creates enough room for 6 people to stay. Located only 1 mile from the quaint Village of Ellicottville and 2 miles from the slopes!

Top guest favorite

A well-lit bathroom features a wooden vanity with sink and storage drawers. A mirror with warm lighting is mounted above the sink. A shower area is partially enclosed by a maroon curtain, and a soft rug lies on the tiled floor.

Home in Ellicottville

4.96 out of 5 average rating, 155 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. Rentals are 30 days+.

Guest favorite

A small log cabin is presented featuring an inviting front porch with a railing. Solar panels are visible on the roof. The surrounding area includes greenery and a gravel pathway, contributing to the rural setting.

Cabin in Great Valley

4.91 out of 5 average rating, 309 reviews

The Porcupine, featuring fiber optic internet

* Get Away From it all The Porcupine is a small, comfortable and private log cabin. And and we are proud to be solar powered! Great for a couple or a family with small children. Rural setting great for hikes or bikes. 3 miles to the village of Ellicottville. 8 miles to the Seneca Allegany Casino. And 2 miles to the slopes of Holiday Valley

Top guest favorite

A charming wooden cabin is nestled among trees, with a welcoming front porch and an American flag waving gently. A circular fire pit surrounded by four adirondack chairs is centrally located on a well-maintained green lawn, with smoke rising softly into the air.

Cabin in Dalton

4.97 out of 5 average rating, 140 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

A light-filled living area features large windows framed by soft curtains, revealing views of the surrounding forest. A comfortable sofa and a fold-out couch provide seating, while a low coffee table holds a decorative bowl and a magazine. Warm, neutral tones enhance the serene atmosphere.

Apartment in Great Valley

4.88 out of 5 average rating, 262 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.