Vacation rentals in Olean

5 out of 5 average rating, 74 reviews

Best Village Location/Firepit/Bar/Games/Yard/etc!

Location, location, location! Center of the village, 1 mile to skiing. Voted top 10 Main St in the US by USA today! Spacious, newly renovated home close to everything, in the center of the village. Walk 100 feet to shops, restaurants, breweries, winery, cafe’s, etc! Fully equipped home for a great getaway anytime. Enjoy the outdoor movie theater, firepit, grill, corn hole and large back yard/deck 😊 Inside, enjoy 9' shuffleboard, photo wall, fireplace, turntable/albums, games, books and bar area!

4.99 out of 5 average rating, 137 reviews

Chalet in Ellicottville

The Mountain View Chalet

The Mountain View Chalet is a spectacular 3,200 sqft 5 bed, 4 bath home tucked in a hill overlooking the Holiday Valley slopes. This is a perfect vacation home for a large extended family or a group of families that enjoy gathering. The two-story wall of windows provides a striking view of the surrounding countryside. A wood burning fireplace, wine chiller, well equipped kitchen, huge deck, and a 6-person hot tub enhances your private surroundings. Winter, spring, summer or fall, you’ll love it!

A sheltered outdoor seating area features soft, cream-colored cushions on wooden furniture. A round, woven rug is centered under a low wooden table. String lights provide gentle illumination, while lush greenery and colorful plants are visible in the background.

4.86 out of 5 average rating, 22 reviews

EVL Zen Retreat:game rm,hot tub,steps 2town&trails

Perfectly located, newly renovated, main ground level of family-friendly ranch home centered between resort and village via a quick walk or minute drive. Extensive amenities, fully equipped kitchen & laundry make this beautifully situated property most convenient! Relaxed & beautiful outdoor space, hot tub, grill, covered deck, seating areas, & backyard. Enjoy outdoors, Holiday Valley golf and ski resort, shopping, dining, & nightlife of the village. This listing is main level of two unit home.

4.95 out of 5 average rating, 43 reviews

A dining area features a large wooden table set for eight, complemented by black dining chairs. Large windows allow natural light to fill the space, highlighting a striking mural on the wall. Warm wood tones and a modern chandelier enhance the ambiance.

Chalet in Ellicottville

Walk to Village! Timber Chalet, Hot-Tub, Bonfire!

Welcome to Skier’s Paradise - our newly designed Ellicottville chalet! Prime location! The chalet is within walking distance to town for quick access to festivals and the lively EVL scene, plus only 5 mins to your favorite outdoor adventure (skiing, hiking, etc.)! This 5 bedroom/3 full bathroom chalet is the perfect 4-season retreat to enjoy with a private hot tub, firepit, wrap around porch w BBQ, gas fireplace, large TVs, fiber optic WiFi & a large grassy area on a 1 acre lot for lawn games.

Superhost

An outdoor patio area features a six-person hot tub under a covered structure, surrounded by cozy seating. String lights illuminate the space, enhancing the tranquil ambiance. A fire table with decorative rocks sits in the center, providing warmth and comfort for evening gatherings.

4.84 out of 5 average rating, 187 reviews

Riverside Retreat 3BR-Games Room-Hot Tub-Fire Pit

Escape to the peacefulness of farm country, just seven minutes from Ellicottville. Our secluded three-bedroom, three-bath home offers stunning escarpment views from the outdoor patio with a hot tub, fire table, fire pit, and BBQ. Inside, enjoy fully furnished rooms and a modern kitchen, complete with a cozy gas fireplace. Our retreat is ideal for families, couples, and groups looking for comfort and convenience. Conveniently located for outdoor activities at nearby Holiday Valley & Holimont.

The spacious living room features a stone fireplace at the center, surrounded by comfortable leather sofas and a wooden coffee table. A large television is mounted above the fireplace. Natural light floods in through expansive windows, illuminating the rustic wooden beams and flooring.

5 out of 5 average rating, 102 reviews

Top Rated! Hot Tub! Gym! Fire pit! Location!

If you're looking for a peaceful place for you and your family to enjoy and make memories, look no further. Enjoy the elegance of this tastefully decorated home directly across the street from a 942 acre Wildlife Management Area and minutes from the restaurants, shops and ski resorts of Ellicottville. 2.8 miles to town, 3.7 miles to Holimont and 4 miles to Holiday Valley. Cuddle up fireside, play games with the kids, make s'mores in the fire pit. You will love this place. New Hot Tub!

4.99 out of 5 average rating, 205 reviews

A serene landscape captures a misty morning view of a tranquil pond surrounded by lush greenery. Trees in autumnal hues line the distance, while a grassy area and scattered seating create a peaceful outdoor setting.

Chalet in Ellicottville

NEW The Hemingway

Cozy & bright, spacious & new, 1 minute drive to town to find a cold brew. 6 minutes to slopes & you'll be on your way BUT you might decide to stay on our comfy couch all day! Your favorite vaca awaits! 2 bed (king + queen), 2 full bath + 1 full size mem foam sofa sleeper. Everything is brand new; modern w/ a twist of Edison bulb. Smart TVs in the bed/living/kit, rain shower, gas fireplace, laundry, dishwasher, wifi. Front entrance & back patio. Beautiful pond w/ 5 acres to roam. 2 night min.

4.98 out of 5 average rating, 110 reviews

The cabin exterior is softly illuminated with string lights, highlighting the wrap-around deck and distinct architecture. A gravel driveway leads to the entrance, with a grassy area surrounding the cabin and a stone wall forming part of the landscape.

Cabin in Ellicottville

Custom-Cozy-Secluded Cabin by Resorts-Hot Tub/Pets

Custom new private cabin in the countryside and not even a mile to the village. The cabin is three total floors including a walk out basement with more space for gear and pets and a fenced in backyard for dogs. Large bonfire pit with plenty of outdoor furniture and a 7 person outdoor hot tub. Three bedrooms, two full bathrooms with an open concept floor plan. Short driveway off of a paved road, huge wrap around deck and gorgeous views. Very close to both Resorts

The kitchen features modern cabinetry with light-colored doors and a large granite island with seating for two. Stainless steel appliances are visible, including a refrigerator and a microwave. Warm lighting illuminates the space, highlighting the tiled backsplash and wooden floor.

4.94 out of 5 average rating, 122 reviews

LOCATION, LOCATION, LOCATION! Walk to EVERYTHING

**We honor local Village laws by Providing 30+ DAY SEASONAL RENTALS** Message for details! You've just found your favorite getaway house in Ellicottville! Perfect location within 2 blocks of the of Village, barely a mile to Holiday Valley! Sleeps 8 w/ 4 bedrooms. Two full bathrooms w/ heated floors. Laundry, DirectTV, internet, gas fireplace & a full kitchen. Two covered decks to relax on. Everything you need for your perfect getaway!

Townhouse in Ellicottville

Snow gently falls over Holiday Valley, creating a serene winter atmosphere. Illuminated ski slopes and trees are visible in the background, enhancing the tranquil setting of this ski resort during the night.

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.

A recreation area features an air hockey table and a shuffleboard table, both set against a neutral-walled backdrop. Vintage skis are displayed on the wall to add character. A small wooden table is positioned in the corner, completing the inviting space.

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+.

4.95 out of 5 average rating, 108 reviews

A mountain view home is set against a backdrop of rolling hills and clear blue skies. Surrounding evergreen trees provide a natural frame, and a well-maintained lawn leads to a gravel pathway. The structure features a charming exterior with multiple peaks.

Condo in Ellicottville

Mountain View at Wildflower walk to town 1 BR loft

Across from Holiday Valley this mountain view home has everything you need for a memorable stay in Ellicottville. A short walk to town. Walk or take the shuttle to the slopes. An ideal place to getaway and relax with family and friends. All the amenities of home. Just bring your favorite food and beverages and leave the rest to us. A well-appointed kitchen, comfy beds and nothing to do but enjoy your stay.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Olean vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Olean's top sights

Beef-N-Barrel Restaurant18 locals recommend

Four Mile Brewing, LLC11 locals recommend

Good Times of Olean7 locals recommend

Walmart Supercenter5 locals recommend

AMC Allegany 85 locals recommend

Union Whiskey5 locals recommend

Other great vacation rentals in Olean

4.92 out of 5 average rating, 150 reviews

Home in Olean

Southern Exposure

Superhost

A cozy kitchen area features a wooden bar with four cushioned stools, providing a comfortable space for dining. Modern stainless-steel appliances are present, alongside dark wood cabinetry. Soft lighting highlights the warm tones of the decor, creating an inviting kitchen atmosphere.

Apartment in Olean

4.81 out of 5 average rating, 114 reviews

Top Shelf Studio

Guest suite in Great Valley

A wooden deck is presented, surrounded by towering trees and lush greenery. A small table with two folding chairs is visible, offering a tranquil spot to enjoy nature. Sunlight filters through the leaves, creating a serene outdoor setting.

4.93 out of 5 average rating, 380 reviews

Comfy studio nestled in the woods (New Listing)

4.96 out of 5 average rating, 134 reviews

The bathroom features a walk-in shower with glass doors, neutral tile flooring, and gray walls. A framed car-themed artwork is displayed, alongside a full-length mirror on the door. Basic amenities, such as a toilet and towel bar, are also included.

Loft in Olean

Joe's Cozy Loft

4.97 out of 5 average rating, 148 reviews

Home in Allegany

Stylish 3-bedroom home near Ellicottville, NY

4.91 out of 5 average rating, 387 reviews

The cabin is set on a grassy area surrounded by trees, featuring a front porch supported by wooden posts. A path made of stones leads to the entrance. The exterior is painted in earthy tones with green trim around the windows.

Cabin in Coudersport

Cozy Country Cabin

Superhost

A stone fireplace is centered in the main room, framed by large picture windows. A vintage-style painting hangs above the mantel. An area with storage baskets and a television is positioned to the left, complemented by warm wooden flooring throughout the space.

Cottage in Olean

4.83 out of 5 average rating, 183 reviews

Artists cottage - mid century