Olean Holiday Rentals

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Our top choices for Olean holiday 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
9.4 out of 10, Exceptional, (18 reviews)
"I loved staying here and would def come again. "
United States
Kaitlyn
The price is AU$223
includes taxes & fees
15 Jan - 16 Jan
Cozy Country Get Away Suite with a view of the Enchanted Mountains

Cozy 1-bedroom house in charming Olean with WiFi

Cozy 1-bedroom house in charming Olean with WiFi
Olean
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Mickenzie V.
The price is AU$256
includes taxes & fees
18 Jan - 19 Jan
Cozy 1-bedroom house in charming Olean with WiFi

Seneca Heights Oasis with Hot Tub

Seneca Heights Oasis with Hot Tub
Olean
9.6 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay! The house is nestled in a really lovely neighborhood. We enjoyed everything the house had to offer. The beds were very comfortable. Will was a great host, and gave us some great suggestions for places to eat. We'll be coming back to stay again. "
United States
Joy
The price is AU$608
includes taxes & fees
24 Jan - 25 Jan
Seneca Heights Oasis with Hot Tub

Stargazer... magnificent, picturesque view

Stargazer... magnificent, picturesque view
Wellsville
9.8 out of 10, Exceptional, (63 reviews)
"Everything was perfect "
United States
Jared M.
The price is AU$327
includes taxes & fees
13 Jan - 14 Jan
Stargazer... magnificent, picturesque view

Rustic Creekside Cabin

Rustic Creekside Cabin
Shinglehouse
9.8 out of 10, Exceptional, (71 reviews)
"Pet friendly, star gazing at its best. Great communications with owner. Lots of hiking nearby"
United States
Mark F.
The price is AU$324
includes taxes & fees
13 Jan - 14 Jan
Rustic Creekside Cabin

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)
"This is the cutest little place! Super clean and tidy. Very cozy. Check in process was super easy. We will be staying here again!"
United States
Debby S.
The price is AU$264
includes taxes & fees
4 Feb - 5 Feb
2-bedroom guest house in charming Cuba with WiFi

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

Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
2.0 star property
Smethport
10.0 out of 10, Exceptional, (1 review)
"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 AU$227
includes taxes & fees
20 Jan - 21 Jan
Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home

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, (46 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 AU$352
includes taxes & fees
13 Jan - 14 Jan
Working farmette at converted warehouse in the Allegany Mountains.

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, (9 reviews)
"Owners are awesome, great place to stay, can’t wait to use again"
United States
Bradley
The price is AU$333
includes taxes & fees
16 Jan - 17 Jan
Active “farmette” New apartment (the Knotty Pine). Nearby restaurants, fitness

Quiet & Cozy Condo–Walk to Town,fireplace ,free shuttle 2 holiday valley resort

Quiet & Cozy Condo–Walk to Town,fireplace ,free shuttle 2 holiday valley resort
2.0 star property
Ellicottville
9.6 out of 10, Exceptional, (20 reviews)
"This property was perfect for my family. Very well kept and communication upon arrival was great!"
United States
Jessica
The price is AU$384
includes taxes & fees
15 Jan - 16 Jan
Quiet & Cozy Condo–Walk to Town,fireplace ,free shuttle 2 holiday valley resort

Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville

Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville
Ellicottville
9.6 out of 10, Exceptional, (10 reviews)
"Great place for a getaway. Close to restaurants and shops. Cozy little place for two!"
United States
Jeremy S.
The price is AU$330
includes taxes & fees
13 Jan - 14 Jan
Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville

Ski-in/out Condo, King Bed + Fireplace

Ski-in/out Condo, King Bed + Fireplace
Ellicottville
9.6 out of 10, Exceptional, (33 reviews)
"Easy check in and nice apartment"
United States
Sanja
The price is AU$417
includes taxes & fees
15 Jan - 16 Jan
Ski-in/out Condo, King Bed + Fireplace

The Eagles Nest

The Eagles Nest
4.5 star property
Ellicottville
9.6 out of 10, Exceptional, (4 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 AU$618
includes taxes & fees
13 Jan - 14 Jan
The Eagles Nest

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, (75 reviews)
"Space was clean and quiet. We loved how pet friendly the house was! The perfect spot for a getaway"
United States
Natalie Q.
The price is AU$330
includes taxes & fees
13 Jan - 14 Jan
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views

Honest Abe Frame @ Sunrise

Honest Abe Frame @ Sunrise
Ellicottville
9.4 out of 10, Exceptional, (3 reviews)
"“This place is absolutely awesome! The rooms are very nice and super clean. The hospitality was outstanding – welcoming, and always ready to help. I truly enjoyed my stay and would highly recommend this place to anyone looking for comfort and great service.”"
United States
PARTH
The price is AU$414
includes taxes & fees
13 Jan - 14 Jan
Honest Abe Frame @ Sunrise

Holiday Valley Ski-In/Ski-Out Condo

Holiday Valley Ski-In/Ski-Out Condo
Great Valley
10.0 out of 10, Exceptional, (55 reviews)
"This location was very relaxing, picturesque, and comfortable. The rooms were clean and everything we had at home (except for food of course) was there for us to use. Great place!"
United States
Jerry
The price is AU$527
includes taxes & fees
25 Jan - 26 Jan
Holiday Valley Ski-In/Ski-Out Condo

Lincoln Boutique Motel- Lower King #3

Lincoln Boutique Motel- Lower King #3
Ellicottville
10.0 out of 10, Exceptional, (1 review)
"Great room. Great experience "
United States
Daniel N.
The price is AU$348
includes taxes & fees
13 Jan - 14 Jan
Lincoln Boutique Motel- Lower King #3

Lincoln Boutique Motel- Lower Room #6

Lincoln Boutique Motel- Lower Room #6
Ellicottville
10.0 out of 10, Exceptional, (1 review)
"The Lincoln Motel was perfect for our one night stay in Ellicottville. Great vibe, contemporary feel, and close to the village. We will be back for sure! "
United States
Anonymous traveller
The price is AU$348
includes taxes & fees
13 Jan - 14 Jan
Lincoln Boutique Motel- Lower Room #6

Breathtaking views, modern container design

Breathtaking views, modern container design
2.0 star property
Little Valley
10.0 out of 10, Exceptional, (2 reviews)
"Quiet, beautiful, great views of the stars, sunset and sunrise! Would love to go back."
United States
Melanie A.
The price is AU$514
includes taxes & fees
2 Feb - 3 Feb
Breathtaking views, modern container design

Charming and cozy studio in Ellicottville, NY

Charming and cozy studio in Ellicottville, NY
Ellicottville
9.8 out of 10, Exceptional, (33 reviews)
"Great communication from the property owners, excellent place to stay. Close to everything, walkable into town of you wanted to. "
United States
CHRISTOPHER
The price is AU$335
includes taxes & fees
13 Jan - 14 Jan
Charming and cozy studio in Ellicottville, NY
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

Everything you need to know about Olean holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Olean holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Olean holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Olean holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Olean holiday rentals we have selected for you start as low as AU$223 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Olean rentals

At Expedia, we put the best Olean holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Olean?

Yes, there are holiday rentals close to the most popular sights in Olean, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Olean has a good selection of restaurants. Make sure you have time to check out the architecture and shopping during your trip.

What are some of the best holiday rentals that Olean has to offer?

Quiet & Cozy Condo–Walk to Town,fireplace ,free shuttle 2 holiday valley resort: This holiday home rental outside of Olean is located near skiing, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Olean?

With 4 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find St. Bonaventure University and Cuba Lake.

What’s a holiday rental in Olean like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Olean. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.