Olean Vacation Rentals

Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Olean vacation rentals

1 bedroom, desk, iron/ironing board, WiFi

Cottage in Olean

Cozy Country Get Away Suite with a view of the Enchanted Mountains
9.2 out of 10, Wonderful, (20 reviews)
"I loved staying here and would def come again. "
United States
Kaitlyn
$130 nightly
The price is $147
Mar 15 - Mar 16
Total with taxes and fees
Cozy Country Get Away Suite with a view of the Enchanted Mountains
Property grounds

Cottage in Wellsville

Stargazer-Magnificent Picturesque View-Dark Skies-Hiking-Biking-Wildlife-Pets
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.
$205 nightly
The price is $231
Mar 15 - Mar 16
Total with taxes and fees
Stargazer-Magnificent Picturesque View-Dark Skies-Hiking-Biking-Wildlife-Pets
Terrace/patio

Cabin in Shinglehouse

Rustic Creekside Cabin
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.
$192 nightly
The price is $212
Mar 15 - Mar 16
Total with taxes and fees
Rustic Creekside Cabin
Exterior

Cabin in Wellsville

Serenity-Private, Secluded Cabin-Scenic Deck View of Sunset- Hiking-Pet friendly
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.
$219 nightly
The price is $246
Mar 15 - Mar 16
Total with taxes and fees
Serenity-Private, Secluded Cabin-Scenic Deck View of Sunset- Hiking-Pet friendly
Exterior detail

Apartment in Cuba

2-bedroom guest house in charming Cuba with WiFi
10.0 out of 10, Exceptional, (9 reviews)
"Incredible home we felt very comfortable "
United States
Kevin L.
$155 nightly
The price is $174
Mar 18 - Mar 19
Total with taxes and fees
2-bedroom guest house in charming Cuba with WiFi
Microwave, oven, stovetop, dishwasher

Vacation Home in Smethport

Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
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.
$133 nightly
The price is $147
Apr 6 - Apr 7
Total with taxes and fees
Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
Terrace/patio

Vacation Home in Machias

REST AT THE NEST! Water front home close to ski slopes and Ellicottville!
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.
$257 nightly
The price is $290
Mar 15 - Mar 16
Total with taxes and fees
REST AT THE NEST! Water front home close to ski slopes and Ellicottville!
Fridge, microwave, oven, stovetop

Apartment in Allegany

Working farmette at converted warehouse in the Allegany Mountains.
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
$203 nightly
The price is $229
Mar 15 - Mar 16
Total with taxes and fees
Working farmette at converted warehouse in the Allegany Mountains.
Interior

Apartment in Allegany

Active “farmette” New apartment (the Knotty Pine). Nearby restaurants, fitness
10.0 out of 10, Exceptional, (10 reviews)
"Owners are awesome, great place to stay, can’t wait to use again"
United States
Bradley
$193 nightly
The price is $218
Mar 17 - Mar 18
Total with taxes and fees
Active “farmette” New apartment (the Knotty Pine). Nearby restaurants, fitness
Property grounds

Chalet in Great Valley

Alpine Hideaway
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.
$257 nightly
The price is $290
Mar 16 - Mar 17
Total with taxes and fees
Alpine Hideaway
Exterior

Condo in Ellicottville

Ski-in/out Condo, King Bed + Fireplace
9.4 out of 10, Exceptional, (35 reviews)
"Great place, will be back. "
Canada
Michael V.
$181 nightly
The price is $204
Mar 15 - Mar 16
Total with taxes and fees
Ski-in/out Condo, King Bed + Fireplace
Front of property

Villa in Ellicottville

The Allen House
3.5 star property
$312 nightly
The price is $353
Mar 24 - Mar 25
Total with taxes and fees
The Allen House
Premium Villa, Mountain View | Terrace/patio

Villa in Ellicottville

The Eagles Nest, Couples Escape - Hot Tub & Views
4.5 star property
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
$361 nightly
The price is $408
Mar 15 - Mar 16
Total with taxes and fees
The Eagles Nest, Couples Escape - Hot Tub & Views
Interior

Apartment in Allegany

Serene 2-bedroom “Barndominium” apartment in Allegany perfect for your getaway
$207 nightly
The price is $233
Mar 21 - Mar 22
Total with taxes and fees
Serene 2-bedroom “Barndominium” apartment in Allegany perfect for your getaway
Interior

Condo in Ellicottville

Cozy Studio Near Holiday Valley & Village
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
$161 nightly
The price is $181
Mar 24 - Mar 25
Total with taxes and fees
Cozy Studio Near Holiday Valley & Village
Exterior

Condo in Ellicottville

Ski-in/out Condo, King Bed, 2 Full Baths
9.8 out of 10, Exceptional, (19 reviews)
"Great place! Will hopefully stay again soon!!! Host was fantastic!!! "
United States
John F.
$212 nightly
The price is $238
Apr 13 - Apr 14
Total with taxes and fees
Ski-in/out Condo, King Bed, 2 Full Baths
Property grounds

Apartment in Ellicottville

Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views
9.8 out of 10, Exceptional, (79 reviews)
"This is the one of the best properties we have rented. The apartment is fantastic, super clean, professionally finished all around with great taste! "
United States
Alexei
$180 nightly
The price is $203
Mar 19 - Mar 20
Total with taxes and fees
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views
Smart TV

Chalet in Ellicottville

Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville
9.6 out of 10, Exceptional, (11 reviews)
"Everything was fabulous! The room was perfect and had everything we needed. It was a perfect getaway!"
United States
Kristin H.
$190 nightly
The price is $215
Mar 24 - Mar 25
Total with taxes and fees
Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville
TV, fireplace, video games, stereo

Condo in Great Valley

Ski-in/out Condo, King Bed + Fireplace
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.
$172 nightly
The price is $193
Apr 14 - Apr 15
Total with taxes and fees
Ski-in/out Condo, King Bed + Fireplace
Property grounds

Vacation Home in Ellicottville

Quiet & Cozy Condo–Walk to Town,fireplace ,free shuttle 2 holiday valley resort
9.6 out of 10, Exceptional, (27 reviews)
"Great spot! Would absolutely stay here again!"
United States
Brittney O.
$209 nightly
The price is $236
Mar 25 - Mar 26
Total with taxes and fees
Quiet & Cozy Condo–Walk to Town,fireplace ,free shuttle 2 holiday valley resort
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

Seneca Allegany Resort & Casino

Seneca Allegany Resort & Casino

10/10 Excellent
"Staff at restaurants were the very best "
Cheryl 1-night trip
Posted 14 hours ago
Seneca Allegany Resort & Casino

Find out more about Olean

Everything you need to know about Olean vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Olean vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Olean vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Olean vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Olean. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Olean in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $147 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Olean rentals

At Expedia, we put the best Olean vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Olean rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Olean vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Olean. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.