Olean Vacation Rentals

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Olean vacation rentals

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

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 ￥12,491
￥22,925 total
includes taxes & fees
Dec 28 - Dec 29
Cozy Country Get Away Suite with a view of the Enchanted Mountains
Exterior detail
Cozy 1-bedroom house in charming Olean with WiFi

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 ￥17,153
￥26,431 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy 1-bedroom house in charming Olean with WiFi
Outdoor spa tub
Seneca Heights Oasis with Hot Tub

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 ￥35,087
￥65,377 total
includes taxes & fees
Dec 27 - Dec 28
Seneca Heights Oasis with Hot Tub
Smart TV, stereo
Stargazer... magnificent, picturesque view

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 ￥18,947
￥33,596 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stargazer... magnificent, picturesque view
Dining
Rustic Creekside Cabin

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 ￥22,923
￥33,574 total
includes taxes & fees
Dec 28 - Dec 29
Rustic Creekside Cabin
Interior
Serenity - Private, secluded cabin-excellant scenic view/sunset, hiking, pond

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 ￥23,157
￥38,508 total
includes taxes & fees
Dec 29 - Dec 30
Serenity - Private, secluded cabin-excellant scenic view/sunset, hiking, pond
Fridge, microwave, oven, stovetop
2-bedroom guest house in charming Cuba with WiFi

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 is well-furnished and in a quiet neighborhood, with easy access to everything in town. The hosts were very responsive, and everything was seamless. "
United States
Lydia
The price is ￥15,594
￥27,193 total
includes taxes & fees
Dec 27 - Dec 28
2-bedroom guest house in charming Cuba with WiFi
Microwave, oven, stovetop, dishwasher
Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home

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 ￥19,648
￥25,115 total
includes taxes & fees
Dec 27 - Dec 28
Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
Fridge, microwave, oven, stovetop
Working farmette at converted warehouse in the Allegany Mountains.

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 ￥25,730
￥36,123 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Working farmette at converted warehouse in the Allegany Mountains.
Dining
Active “farmette” New apartment (the Knotty Pine). Nearby restaurants, fitness

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 ￥24,171
￥34,538 total
includes taxes & fees
Dec 30 - Dec 31
Active “farmette” New apartment (the Knotty Pine). Nearby restaurants, fitness
Exterior
Cozy newly remodeled private home just 10 mins from Ellicottville.

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 ￥31,500
￥40,705 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy newly remodeled private home just 10 mins from Ellicottville.
Villa, Mountain View | Private kitchen | Full-size fridge, microwave, oven, stovetop
The Eagles Nest

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 ￥41,465
￥64,478 total
includes taxes & fees
Jan 13 - Jan 14, 2026
The Eagles Nest
Exterior
Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville

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, (9)
"Great place for a getaway. Close to restaurants and shops. Cozy little place for two!"
United States
Jeremy S.
The price is ￥24,950
￥40,176 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville
Terrace/patio
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views

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 ￥26,354
￥46,168 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views
Fridge, microwave, oven, stovetop
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

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 ￥18,713
￥40,353 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Quiet & Cozy Condo–Walk to Town,fireplace ,free shuttle 2 holiday valley resort
Outdoor dining
Cozy Studio Near Holiday Valley & Village

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.
The price is ￥20,506
￥38,307 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Studio Near Holiday Valley & Village
Dining
4 Seasons of Fun, Ellicottville house that sleeps 16!

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 ￥56,918
￥142,379 total
includes taxes & fees
Jan 5 - Jan 6, 2026
4 Seasons of Fun, Ellicottville house that sleeps 16!
Terrace/patio
Hillside Getaway Ski-In Ski-Out Retreat in Ellicottville, NY Sleeps 4

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
Desk, free WiFi, bed sheets
Honest Abe Frame @ Sunrise

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
The price is ￥35,929
￥53,357 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Honest Abe Frame @ Sunrise
Exterior
Charming 2-bedroom condo in superb Ellicottville with AC, WiFi

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 ￥51,460
￥81,410 total
includes taxes & fees
Jan 23 - Jan 24, 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

Quality Inn & Suites

Quality Inn & Suites

10/10 Excellent
"I arrived an hour early and they allowed me to check in. I really appreciated that service"
JAMES 1-night trip
Posted 3 days ago
Quality Inn & Suites

Find out more about Olean

Search for holiday rentals in Olean on Expedia! You can easily find your home rentals, villas, holiday apartments in Olean using one of the methods below:

  • View our selection of featured holiday rentals in Olean
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  • Enter your travel dates to view the best deals on holiday rentals in Olean while they last

Look no further and take a look at our great range of rental properties in Olean!

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?

-RARE- In-Village rental! 4-Bedrooms w HOT TUB & AC : This vacation home rental near Olean offers a patio, a selection of games, and a barbecue grill 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 you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

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.