Holiday Rentals in Olean

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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)
"I loved staying here and would def come again. "
United States
Kaitlyn
The price is €129
includes taxes & fees
28 Dec - 29 Dec
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)
"Great stay!"
United States
Mickenzie V.
The price is €148
includes taxes & fees
31 Dec - 1 Jan 2026
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)
"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 €365
includes taxes & fees
27 Dec - 28 Dec
Seneca Heights Oasis with Hot Tub

Stargazer... magnificent, picturesque view

Stargazer... magnificent, picturesque view
Wellsville
9.8 out of 10, Exceptional, (62)
"Lovely cottage w great views. Easy check-in, very quiet, and perfect for us with a dog. Quite pleased..."
United States
Thomas P.
The price is €189
includes taxes & fees
1 Jan - 2 Jan 2026
Stargazer... magnificent, picturesque view

Rustic Creekside Cabin

Rustic Creekside Cabin
Shinglehouse
9.8 out of 10, Exceptional, (71)
"Pet friendly, star gazing at its best. Great communications with owner. Lots of hiking nearby"
United States
Mark F.
The price is €187
includes taxes & fees
28 Dec - 29 Dec
Rustic Creekside Cabin

Serenity - Private, secluded cabin-excellant scenic view/sunset, hiking, pond

Serenity - Private, secluded cabin-excellant scenic view/sunset, hiking, pond
Wellsville
9.6 out of 10, Exceptional, (65)
"Great location, great view off the deck. Maintained hiking trails was a great feature."
United States
Bryan G.
The price is €213
includes taxes & fees
29 Dec - 30 Dec
Serenity - Private, secluded cabin-excellant scenic view/sunset, hiking, pond

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)
"The property was clean and cozy. It was pretty quiet. We didn’t spend a lot of time in the unit but when we did it was like home. "
United States
Patricia H.
The price is €152
includes taxes & fees
26 Dec - 27 Dec
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)
"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 €140
includes taxes & fees
26 Dec - 27 Dec
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, (45)
"We have stayed here multiple times and always enjoy our time. Great location and hosts."
United States
Marc N.
The price is €205
includes taxes & fees
1 Jan - 2 Jan 2026
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)
"Owners are awesome, great place to stay, can’t wait to use again"
United States
Bradley
The price is €195
includes taxes & fees
1 Jan - 2 Jan 2026
Active “farmette” New apartment (the Knotty Pine). Nearby restaurants, fitness

Cozy newly remodeled private home just 10 mins from Ellicottville.

Cozy newly remodeled private home just 10 mins from Ellicottville.
Franklinville
10.0 out of 10, Exceptional, (25)
"Beautiful property, so fabulously decorated- it had absolutely everything you need - such a great vacation place will definitely go back"
Canada
Tara
The price is €227
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy newly remodeled private home just 10 mins from Ellicottville.

The Eagles Nest

The Eagles Nest
4.0 star property
Ellicottville
9.6 out of 10, Exceptional, (4)
"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 €350
includes taxes & fees
13 Jan - 14 Jan 2026
The Eagles Nest

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, (8)
"Great place for a getaway. Close to restaurants and shops. Cozy little place for two!"
United States
Jeremy S.
The price is €217
includes taxes & fees
13 Jan - 14 Jan 2026
Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville

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)
"Clean, great location and everything you need for a visit to Ellicottville. "
United States
Anna
The price is €257
includes taxes & fees
4 Jan - 5 Jan 2026
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views

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, (19)
"This property was perfect for my family. Very well kept and communication upon arrival was great!"
United States
Jessica
The price is €225
includes taxes & fees
11 Jan - 12 Jan 2026
Quiet & Cozy Condo–Walk to Town,fireplace ,free shuttle 2 holiday valley resort

Cozy Studio Near Holiday Valley & Village

Cozy Studio Near Holiday Valley & Village
Ellicottville
10.0 out of 10, Exceptional, (14)
"Great stay, very clean and many amenities! Hope to stay here again in the future!"
United States
Beth A.
Cozy Studio Near Holiday Valley & Village

4 Seasons of Fun, Ellicottville house that sleeps 16!

4 Seasons of Fun, Ellicottville house that sleeps 16!
Great Valley
10.0 out of 10, Exceptional, (4)
"We enjoyed our stay at this property. The decor was lovely, kitchen and home well stocked, and everything very thoughtfully designed for a family to enjoy. "
United States
Christa Z.
The price is €807
includes taxes & fees
12 Jan - 13 Jan 2026
4 Seasons of Fun, Ellicottville house that sleeps 16!

Hillside Getaway Ski-In Ski-Out Retreat in Ellicottville, NY Sleeps 4

Hillside Getaway Ski-In Ski-Out Retreat in Ellicottville, NY Sleeps 4
Ellicottville
9.8 out of 10, Exceptional, (23)
"Beautifully decorated and clean Ellicottville is a fun town to visit"
United States
Kristen D.
Hillside Getaway Ski-In Ski-Out Retreat in Ellicottville, NY Sleeps 4

Honest Abe Frame @ Sunrise

Honest Abe Frame @ Sunrise
Ellicottville
9.4 out of 10, Exceptional, (3)
"“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
Honest Abe Frame @ Sunrise

Charming 2-bedroom condo in superb Ellicottville with AC, WiFi

Charming 2-bedroom condo in superb Ellicottville with AC, WiFi
Ellicottville
9.8 out of 10, Exceptional, (8)
"Beautiful place, felt very homey and comfortable. I am definitely looking to stay again in February. "
United States
Karen K.
The price is €454
includes taxes & fees
23 Jan - 24 Jan 2026
Charming 2-bedroom condo in superb Ellicottville with AC, WiFi
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, apart-hotels, 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 favorite 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 depends 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 €129 per night. Entering your travel dates in the search wizard you might find 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. 

Explore a world of travel with Expedia

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?

-RARE- In-Village rental! 4-Bedrooms w HOT TUB & AC : This holiday home rental outside of Olean offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub 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.