Holiday rentals in Olean

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Top-rated holiday rentals in Olean

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The cabin exterior features a rustic wooden structure with a welcoming entrance. A spacious deck with seating is visible, surrounded by lush greenery. A grill and prep area are set up near the entrance, providing an inviting spot for outdoor meals. A friendly pet can be seen nearby.
Tiny home in Machias
4.87 out of 5 average rating, 432 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.

Top guest favourite
A cozy sleeping space features a spacious bed with crisp white linens. A decorative throw blanket in golden hues is placed at the foot of the bed. A bedside table holds a lamp and a decorative bowl, while a window with sheer curtains allows natural light to enter.
Guest suite in Houghton
4.97 out of 5 average rating, 108 reviews

Houghton Brookside Retreat

Relax in this spacious, serene space, surrounded by nature. Enjoy your morning coffee on the large deck. Perfect for a get-away, visiting your college student at Houghton University (walking distance), hiking in Letchworth State Park, antiquing in Angelica or Cuba. In the well appointed and stocked kitchen you will be greeted by homemade bread, coffee, fruit, and breakfast essentials. This private space is on the lower level so guests must be able to navigate a set of stairs. Off-street parking.

Guest favourite
A cabin is nestled among tall pine trees, showcasing a rustic wooden exterior and a welcoming porch. The surrounding landscape reveals vibrant autumn foliage in hues of orange and red, creating a serene and secluded atmosphere.
Cabin in Ellicottville
4.94 out of 5 average rating, 105 reviews

Stylish & Secluded Hideaway, 5 mins to EVL

This private space is quietly tucked away in a stand of pines in the woods alongside Bryant Hill Creek. A wall of windows brings nature and natural light pouring into the space, and a fully-equipped kitchen and European bathroom provide modern comfort. Less than 4 miles outside of E-ville, it comfortably sleeps 2 adults and offers a chic and romantic setting for a couple to hide away with easy access to downtown. 4x4 a must in the snow, or simply park at the foot of the driveway. Tv & wifi.

Guest favourite
A comfortable living area features a sofa positioned across from a gas fireplace. A large television is mounted above a wooden shelf, creating a functional space. Natural light flows in through sliding glass doors that open to a grassy outdoor area.
Apartment in Ellicottville
4.93 out of 5 average rating, 164 reviews

Ski In/Out Condo, King Bed

This 1-bedroom ski-in/ski-out condo (with a king bed!) and full bathroom is perfect for a couple or a small family. Freshly renovated in September 2023 with new paint, furniture, and kitchen updates. Walk or ski to the SnowPine and Sunrise lifts at Holiday Valley, just a few miles from town. An hourly shuttle can take you to the main lodge. Enjoy easy access to mountain biking and hiking trails in the summer. Includes parking, a gas fireplace, high-speed internet, Roku TV, and access to shared l

Top guest favourite
A welcoming wooden sign reading 'WILDFLOWER' is prominently displayed at the entrance, framed by well-maintained greenery and colorful landscaping. The stone base adds an earthy texture, while nearby trees are dotted with budding branches, suggesting a peaceful environment.
Apartment in Ellicottville
4.95 out of 5 average rating, 353 reviews

Loft Condo in Wildflower

This is a ground level loft condo that is bright, clean and nicely updated. We are minutes from the Holiday Valley Resort and a short walk to the Village of Ellicottville. This condo offers AC for the summer and a gas fireplace for the winter. We have complimentary coffee and tea with cream and sugar on site. Kitchen is equipped with some spices, oils and cookware. We also supply clean linens and towels. This place is great for 2 to 6 guest for family or close friends with 3 beds and a futon .

Guest favourite
A spacious living area is highlighted by green walls and natural light filtering through two windows. A stone fireplace serves as a focal point, with a television mounted above. Comfortable seating includes a dark sectional sofa and a leather armchair. A wooden coffee table occupies the center.
Loft in Olean
4.96 out of 5 average rating, 149 reviews

Joe's Cozy Loft

Joe's Cozy Loft is now under new management! Expect the same great accommodations and amenities as before but with seamless and Superhost service. Your stay with us includes wifi, off street parking after business hrs, a luxurious 2 person jet tub, laundry capabilities, a private deck with grill and more. We are a short walk or drive to many local restaurants and taverns. We are nestled in the heart of the the Enchanted Mountains with easy access to Ellicottville skiing, Buffalo and much more!

Guest favourite
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, 190 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 favourite
The spacious main living area features a dark sofa and a wooden coffee table, complemented by a decorative area rug. A kitchenette is visible in the background, equipped with wooden cabinetry and essential appliances. A dining space with a small round table is also present, enhancing the functionality of the space.
Flat in Little Valley
4.91 out of 5 average rating, 129 reviews

Hidden Haven, 6 mi. outside EVL

Welcome to The Hidden Haven, nestled in the heart of the Enchanted Mountains of WNY, just outside of EVL, NY. If you're looking to stay close to town, but outside the chaos, this is the place. It's less than 10 min, almost a straight shot, to town and the slopes at Holiday Valley and Holimont. This apartment is hidden in the barn of an old dairy farm, adjacent to the main house. You'll be able to enjoy your own quiet hideout as well as the scenic drive through the valley on your way to town.

Guest favourite
A spacious living area is highlighted by a large brown leather sectional sofa adorned with decorative pillows. A vintage wooden trunk serves as a coffee table, topped with a lantern, a decorative orb, and a small plant. Soft light filters through sheer curtains.
Home in Allegany
4.96 out of 5 average rating, 158 reviews

Stylish 3-bedroom home near Ellicottville, NY

Stylish, entire residential 3 bedroom/ 1 bath home. Close to Ellicottville/skiing -30 mins., St. Bonaventure University, Cutco, Rock City Park, Allegany State Park, kayak launch, biking, and walking trail. Niagara Falls is a 1.5-hour drive, Zippo 30 minutes. Walmart and movie theater are 2 miles away. Many restaurants are nearby. A seasonal 2 screen drive-in movie theater-20 min. drive. 2 queen beds , 1 double bed, and a chair converts to a twin size bed. Fully equipped kitchen.

Top guest favourite
The living room features a comfortable brown sofa and a red accent chair, complemented by a round coffee table. Natural light enters through sliding doors, connecting to an outdoor area. Nearby, a modern fireplace is visible, along with rustic wall art and wooden accents.
Apartment in Ellicottville
4.89 out of 5 average rating, 352 reviews

King Bed, A/C, Pickleball, Patio w/ Grill

Enjoy a cozy, renovated condo at SnowPine Village—perfect for summer adventures, with true ⛷️ ski-in/ski-out access in winter! 🛏 King bed + loft w/ bunks – Sleeps 6 🍳 Fully stocked kitchen 🏓 Pickleball courts on-site ❄️ Mini-split A/C – Stay cool in summer 🏡 Covered patio w/ grill & seating 📶 Fast WiFi + Roku TVs 📍 Short drive to Ellicottville & Holiday Valley ⛷️ Ski-in/ski-out access (winter) 🚙 Ample parking (2-car limit in ski season) ☀️ Great for hiking & outdoor fun

Top guest favourite
A charming cabin with a wooden exterior is set against a green lawn. The structure features multiple windows, allowing natural light to enter. A small staircase leads to the entrance, while a fenced yard surrounds the property, offering a sense of privacy and space.
Barn in Cuba
4.98 out of 5 average rating, 199 reviews

Stylish & Inviting, Close to lake, 1BR-Sleeps 2

This unique place has a style all its own. This 1BR space "delivers" when it comes to comfort and convenience. Comes with a fully equipped kitchen and all the amenities to make your stay as comfortable and easy as possible. Has a deck if you would like to just relax or enjoy a meal. This cozy space is on the second story so if you have a hard time with stairs sadly we aren't the place for you. Try us out, you won't be disappointed!!

Guest favourite
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.
Guest suite in Great Valley
4.92 out of 5 average rating, 398 reviews

Comfy studio nestled in the woods (New Listing)

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

Popular amenities for Olean holiday rentals

When is the best time to visit Olean?

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Quick stats about holiday rentals in Olean

  • Total holiday rentals

    Explore 50 holiday rentals in Olean

  • Nightly prices starting at

    Olean holiday rentals start at ₹4,392 per night before taxes and fees

  • Verified guest reviews

    Over 2,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Olean holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Olean rentals

  • 4.8 Average rating

    Olean stays are highly rated by guests – averaging 4.8 out of 5!

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