Olean Vacation Rentals

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Our top choices for Olean vacation rentals

Cozy Country Get Away Suite with a view of the Enchanted Mountains

Cozy Country Get Away Suite with a view of the Enchanted Mountains
Olean
9.2 out of 10, Wonderful, (20 reviews)
"I loved staying here and would def come again. "
United States
Kaitlyn
The price is CA $109
CA $199 total
includes taxes & fees
Mar 20 - Mar 21
Cozy Country Get Away Suite with a view of the Enchanted Mountains

Rustic Creekside Cabin

Rustic Creekside Cabin
Shinglehouse
9.8 out of 10, Exceptional, (72 reviews)
"Pet friendly, star gazing at its best. Great communications with owner. Lots of hiking nearby"
United States
Mark F.
The price is CA $200
CA $292 total
includes taxes & fees
Mar 11 - Mar 12
Rustic Creekside Cabin

Stargazer-Magnificent Picturesque View-Dark Skies-Hiking-Biking-Wildlife-Pets

Stargazer-Magnificent Picturesque View-Dark Skies-Hiking-Biking-Wildlife-Pets
Wellsville
9.8 out of 10, Exceptional, (63 reviews)
"Warm and cozy, plenty of room to be comfortable with a large dog. Amazing views as always! A home away from home with allThe conveniences. Wanted to hike the trails, but my dog wasn’t a fan of of the deeper snow, despite his long legs. Having stayed here in the summer, I know the woods and trails would have been beautiful. "
United States
Lori F.
The price is CA $183
CA $321 total
includes taxes & fees
Mar 13 - Mar 14
Stargazer-Magnificent Picturesque View-Dark Skies-Hiking-Biking-Wildlife-Pets

Serenity-Private, Secluded Cabin-Scenic Deck View of Sunset- Hiking-Pet friendly

Serenity-Private, Secluded Cabin-Scenic Deck View of Sunset- Hiking-Pet friendly
Wellsville
9.6 out of 10, Exceptional, (65 reviews)
"Great location, great view off the deck. Maintained hiking trails was a great feature."
United States
Bryan G.
The price is CA $202
CA $343 total
includes taxes & fees
Mar 16 - Mar 17
Serenity-Private, Secluded Cabin-Scenic Deck View of Sunset- Hiking-Pet friendly

2-bedroom guest house in charming Cuba with WiFi

2-bedroom guest house in charming Cuba with WiFi
Cuba
10.0 out of 10, Exceptional, (8 reviews)
"Incredible home we felt very comfortable "
United States
Kevin L.
The price is CA $136
CA $237 total
includes taxes & fees
Apr 2 - Apr 3
2-bedroom guest house in charming Cuba with WiFi

REST AT THE NEST! Water front home close to ski slopes and Ellicottville!

REST AT THE NEST! Water front home close to ski slopes and Ellicottville!
Machias
10.0 out of 10, Exceptional, (80 reviews)
"We came for the fall fest, this location was great. Exactly as listed ans had everything we could need. "
United States
Kristen D.
The price is CA $237
CA $393 total
includes taxes & fees
Mar 12 - Mar 13
REST AT THE NEST! Water front home close to ski slopes and Ellicottville!

The Eagles Nest, Couples Escape - Hot Tub & Views

The Eagles Nest, Couples Escape - Hot Tub & Views
4.5 star property
Ellicottville
9.6 out of 10, Exceptional, (5 reviews)
"Our stay was perfect. The property manager, Jess, is very nice and was very relaxed and accommodating. The home had everything we needed and then some. Lots of space to relax, amazing views, and very peaceful. "
United States
Erin
The price is CA $354
CA $553 total
includes taxes & fees
Mar 11 - Mar 12
The Eagles Nest, Couples Escape - Hot Tub & Views

Working farmette at converted warehouse in the Allegany Mountains.

Working farmette at converted warehouse in the Allegany Mountains.
Allegany
9.8 out of 10, Exceptional, (49 reviews)
"Owner is very caring and welcoming. Love seeing the farm animals daily and the ping pong table was used daily by the teenagers. Will stay again when visiting family again. Amazing stay"
United States
Randall
The price is CA $224
CA $317 total
includes taxes & fees
Apr 2 - Apr 3
Working farmette at converted warehouse in the Allegany Mountains.

Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home

Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
Smethport
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed a cozy weekend to celebrate an early Christmas. The house is very spacious with lots of comfy beds and plenty of bathrooms. It's within walking distance to a grocery store and hardware store. It's right next to a beer distributor in case you need some bevs for your stay! The hosts are very easy to get a hold of and are very responsive if you need anything. Check in and check out process was easy-peasy. I would recommend this place!"
United States
Caitie H.
The price is CA $159
CA $205 total
includes taxes & fees
Mar 16 - Mar 17
Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home

Active “farmette” New apartment (the Knotty Pine). Nearby restaurants, fitness

Active “farmette” New apartment (the Knotty Pine). Nearby restaurants, fitness
Allegany
10.0 out of 10, Exceptional, (10 reviews)
"Owners are awesome, great place to stay, can’t wait to use again"
United States
Bradley
The price is CA $210
CA $301 total
includes taxes & fees
Apr 2 - Apr 3
Active “farmette” New apartment (the Knotty Pine). Nearby restaurants, fitness

The Allen House

The Allen House
3.5 star property
Ellicottville
The price is CA $292
CA $479 total
includes taxes & fees
Apr 2 - Apr 3
The Allen House

Ski-in/out Condo, King Bed, 2 Baths, Gas Fireplace

Ski-in/out Condo, King Bed, 2 Baths, Gas Fireplace
Ellicottville
10.0 out of 10, Exceptional, (68 reviews)
"The place was amazing and the host was very responsive. "
United States
Anonymous traveller
The price is CA $197
CA $408 total
includes taxes & fees
Mar 17 - Mar 18
Ski-in/out Condo, King Bed, 2 Baths, Gas Fireplace

Ski-in/out Condo, King Bed, 2 Full Baths

Ski-in/out Condo, King Bed, 2 Full Baths
Ellicottville
9.8 out of 10, Exceptional, (19 reviews)
"Great place! Will hopefully stay again soon!!! Host was fantastic!!! "
United States
John F.
The price is CA $153
CA $331 total
includes taxes & fees
Mar 11 - Mar 12
Ski-in/out Condo, King Bed, 2 Full Baths

Alpine Hideaway

Alpine Hideaway
Great Valley
10.0 out of 10, Exceptional, (1 review)
"neat and tidy all amenities comfortable beds only thing my son didn't like to pull out mattress we would come back in a minute thank you for your hospitality."
United States
Tim P.
The price is CA $306
CA $393 total
includes taxes & fees
Mar 11 - Mar 12
Alpine Hideaway

Huge Home & Studio-Hot Tub-Sauna-Pet Friendly-Amazing Views

Huge Home & Studio-Hot Tub-Sauna-Pet Friendly-Amazing Views
Ellicottville
10.0 out of 10, Exceptional, (9 reviews)
"Awesome property! "
United States
Rashmi V.
The price is CA $639
CA $1,307 total
includes taxes & fees
Mar 11 - Mar 12
Huge Home & Studio-Hot Tub-Sauna-Pet Friendly-Amazing Views

Ski-in/out Condo, King Bed + Fireplace

Ski-in/out Condo, King Bed + Fireplace
Great Valley
9.8 out of 10, Exceptional, (85 reviews)
"Clean and well supplied. Nice back deck where the family enjoyed playing games that were available. Enjoyed our stay."
United States
Carrie B.
The price is CA $139
CA $296 total
includes taxes & fees
Mar 17 - Mar 18
Ski-in/out Condo, King Bed + Fireplace

Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views

Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views
Ellicottville
9.8 out of 10, Exceptional, (78 reviews)
"Super cute place! Very cozy we all enjoyed our stay. Thank you "
United States
Scott R M.
The price is CA $136
CA $278 total
includes taxes & fees
Mar 25 - Mar 26
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views

Tahoe Studio

Tahoe Studio
Ellicottville
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful tiny home in a perfect place. Nice amenities, paved walk ways. Nice parking lot. Quiet and beautiful area."
United States
Allison H.
The price is CA $271
CA $515 total
includes taxes & fees
Apr 2 - Apr 3
Tahoe Studio

Cozy Studio Near Holiday Valley & Village

Cozy Studio Near Holiday Valley & Village
Ellicottville
10.0 out of 10, Exceptional, (17 reviews)
"Great place across the road from The ski hill and close to town. Great coffee station with keurig, nespresso and even coffee beans and grinder if you wanted to brew a pot! Clean and cozy would definitely book again! "
Canada
Leslie
The price is CA $111
CA $246 total
includes taxes & fees
Mar 24 - Mar 25
Cozy Studio Near Holiday Valley & Village

UNIQUE Log Style Cozy Ski Chalet - Walking Distance To Town - Pets Welcome

UNIQUE Log Style Cozy Ski Chalet - Walking Distance To Town - Pets Welcome
Ellicottville
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful property close to everything!"
United States
joshua m.
The price is CA $379
CA $793 total
includes taxes & fees
Apr 2 - Apr 3
UNIQUE Log Style Cozy Ski Chalet - Walking Distance To Town - Pets Welcome
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Olean Hotel Reviews

Find out more about Olean

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Olean. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Olean?

Yes, you can find vacation rentals close to top attractions in Olean, or you can select a more secluded option if you want a relaxing place to stay. Our travelers say Olean has a good selection of restaurants. Make sure you have time to check out the architecture and shopping during your trip.

What's the top vacation rental that Olean has to offer?

⛷️ Stunning 8 Bed Mountain Chalet | Steps from Holiday Valley | Hot Tub, Sauna, Theatre & Bar: This vacation home rental near Olean is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Olean?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Olean stay.

What’s there to see and do in Olean?

Allegheny River and Gargoyle Park are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find St. Bonaventure University and Cuba Lake.

What’s a vacation rental in Olean like?

Vacation rentals are private properties you can book for several days or more in Olean. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family gatherings.