A river winding through a green landscape with a town in the background.

Olean Holiday Rentals

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Our top choices for Olean holiday rentals

1. 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
9.0 out of 10, Wonderful, (32 reviews)
"Was a nice spot you relax while in town for a softball tournament!"
United States
Denise
The price is NZ$255
includes taxes & fees
23 Sept - 24 Sept
Cozy Country Get Away Suite with a view of the Enchanted Mountains

2. Working farmette at converted warehouse in the Allegany Mountains.

Working farmette at converted warehouse in the Allegany Mountains.
Allegany
10.0 out of 10, Exceptional, (65 reviews)
"Loved the place very spacious."
United States
Philip M.
The price is NZ$382
includes taxes & fees
30 Sept - 1 Oct
Working farmette at converted warehouse in the Allegany Mountains.

3. Serene 2-bedroom “Barndominium” apartment in Allegany perfect for your getaway

Serene 2-bedroom “Barndominium” apartment in Allegany perfect for your getaway
Allegany
10.0 out of 10, Exceptional, (7 reviews)
"I wish there were more stars to give!The property is exquisite and the house brand new. There is nothing more you’d want or need staying here. The animals and experience being on the farm brought us serenity and peace. Chuck and Angela are the most wonderful hosts who have become friends. We are truly blessed to have stayed at the Barndominium!"
United States
Trish D.
The price is NZ$427
includes taxes & fees
30 Sept - 1 Oct
Serene 2-bedroom “Barndominium” apartment in Allegany perfect for your getaway

4. 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, (13 reviews)
"Cute little place in a nice small town."
United States
Abigail
The price is NZ$332
includes taxes & fees
7 Oct - 8 Oct
2-bedroom guest house in charming Cuba with WiFi

5. SnowPine Condo, King Bed, Patio + Fireplace

SnowPine Condo, King Bed, Patio + Fireplace
Ellicottville
9.4 out of 10, Exceptional, (37 reviews)
"Great place, will be back. "
Canada
Michael V.
SnowPine Condo, King Bed, Patio + Fireplace

6. Cozy Studio Near Holiday Valley & Village

Cozy Studio Near Holiday Valley & Village
Ellicottville
10.0 out of 10, Exceptional, (21 reviews)
"outstanding well equipped so cute clean i would totally recommend this Host the location awesome the little town super cute"
United States
Crewzilla K.
The price is NZ$336
includes taxes & fees
21 Sept - 22 Sept
Cozy Studio Near Holiday Valley & Village

7. Holiday Valley Ski-In/Ski-Out Condo

Holiday Valley Ski-In/Ski-Out Condo
Great Valley
10.0 out of 10, Exceptional, (72 reviews)
"This place was great! Outstanding location for both summer activities and skiing. It was very clean, and Mikayla was very responsive. We'd definitely stay here again!"
United States
Chris B.
The price is NZ$496
includes taxes & fees
21 Sept - 22 Sept
Holiday Valley Ski-In/Ski-Out Condo

8. SnowPine Condo, Sleeps 6, Patio, A/C

SnowPine Condo, Sleeps 6, Patio, A/C
Ellicottville
9.8 out of 10, Exceptional, (79 reviews)
"Loved our stay!"
United States
Shannon S.
The price is NZ$383
includes taxes & fees
21 Sept - 22 Sept
SnowPine Condo, Sleeps 6, Patio, A/C

9. SnowPine Condo, King Bed, 2 Full Baths

SnowPine Condo, King Bed, 2 Full Baths
Ellicottville
9.8 out of 10, Exceptional, (23 reviews)
"Great location to the slopes. "
United States
Michelle L.
The price is NZ$408
includes taxes & fees
22 Sept - 23 Sept
SnowPine Condo, King Bed, 2 Full Baths

10. Walk to Slopes & Town Studio

Walk to Slopes & Town Studio
Ellicottville
9.8 out of 10, Exceptional, (43 reviews)
"Great place. Perfect for 2 people, neat and tidy, very comfortable, great location."
United States
John H.
The price is NZ$246
includes taxes & fees
21 Sept - 22 Sept
Walk to Slopes & Town Studio

11. 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, (71 reviews)
"The history was responsive to needs and easy to reach before and during our trip. The house had everything we needed for a weekend stay. We only had to bring our own food and personal toiletries. The view was amazing and exactly as expected from the photos provided. The area was secluded and quiet, which made for a much needed peaceful weekend."
United States
celeste b.
The price is NZ$471
includes taxes & fees
21 Sept - 22 Sept
Stargazer-Magnificent Picturesque View-Dark Skies-Hiking-Biking-Wildlife-Pets

12. Quiet & Cozy Condo. Cool A/C & streaming. Walk to town & Holiday Valley

Quiet & Cozy Condo. Cool A/C & streaming. Walk to town & Holiday Valley
Ellicottville
9.6 out of 10, Exceptional, (34 reviews)
"Wonderful condo! Great location, perfectly described with lots of amenities not listed. Easy check in. Stacey is a great host and we look forward to staying again! Great off season value too. So nice to just relax but also lots to do!"
United States
Anonymous traveller
The price is NZ$453
includes taxes & fees
27 Sept - 28 Sept
Quiet & Cozy Condo. Cool A/C & streaming. Walk to town & Holiday Valley

13. 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, (84 reviews)
"nice place - peaceful and water was nice and relaxing! "
United States
Lisa D.
The price is NZ$367
includes taxes & fees
22 Sept - 23 Sept
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views

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

Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
Smethport
9.4 out of 10, Exceptional, (13 reviews)
"Cozy is a great way to describe this house. We felt right at home when we checked in."
United States
Carissa C.
The price is NZ$399
includes taxes & fees
22 Sept - 23 Sept
Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home

15. Ebb~n~Flow-Rustic-Solar Cabin-Heated-Hiking-Biking-Pond-Wildlife-Dark Skies-Pets

Ebb~n~Flow-Rustic-Solar Cabin-Heated-Hiking-Biking-Pond-Wildlife-Dark Skies-Pets
Wellsville
9.8 out of 10, Exceptional, (21 reviews)
"Really enjoyed the isolated cabin on a beautiful property. We had a fantastic stay. "
United States
Anonymous traveller
The price is NZ$448
includes taxes & fees
18 Sept - 19 Sept
Ebb~n~Flow-Rustic-Solar Cabin-Heated-Hiking-Biking-Pond-Wildlife-Dark Skies-Pets

16. 2-bedroom apartment in Village of Ellicottville perfect for your getaway.

2-bedroom apartment in Village of Ellicottville perfect for your getaway.
Ellicottville
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! The property was clean, comfortable, and exactly as described. The location was great, and everything we needed was readily available. The host was friendly, responsive, and made the entire experience easy from start to finish. We would definitely stay here again and highly recommend it to others!"
United States
Erin W.
The price is NZ$385
includes taxes & fees
28 Sept - 29 Sept
2-bedroom apartment in Village of Ellicottville perfect for your getaway.

17. Ski In/Out Condo with King Bed, Fireplace & Patio

Ski In/Out Condo with King Bed, Fireplace & Patio
Great Valley
The price is NZ$302
includes taxes & fees
27 Sept - 28 Sept
Ski In/Out Condo with King Bed, Fireplace & Patio

18. Rustic Creekside Cabin

Rustic Creekside Cabin
Shinglehouse
9.8 out of 10, Exceptional, (76 reviews)
"It was such a great gateway! We loved every second of it. And especially my dog who could run around. We explored a pond and a trail in the forest! Overall was so peaceful. A recharge much needed. It was a bit cool outside and so cozy in the cabin. There’s everything that you need there. Portable water. There’s a grill you can make food or just heat it on the stove. Hopefully, we’ll be able to come back. Thank you for amazing experience!"
United States
Kateryna P.
The price is NZ$372
includes taxes & fees
22 Sept - 23 Sept
Rustic Creekside Cabin

19. Blue Moon - Dark Skies, Spacious, Quiet, Fully Furnished Campsite

Blue Moon - Dark Skies, Spacious, Quiet, Fully Furnished Campsite
Wellsville
10.0 out of 10, Exceptional, (1 review)
"Fantastic camp, so very well thought out and charming. Highly recommended!"
United States
Kal W.
The price is NZ$322
includes taxes & fees
21 Sept - 22 Sept
Blue Moon - Dark Skies, Spacious, Quiet, Fully Furnished Campsite

20. The Devereaux House in Ellicottville NY

The Devereaux House in Ellicottville NY
Ellicottville
10.0 out of 10, Exceptional, (2 reviews)
"Great place! "
United States
Cathleen B.
The price is NZ$732
includes taxes & fees
20 Sept - 21 Sept
The Devereaux House 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 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 NZ$255 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. 

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?

Fantastic lake house on the south shore of Cuba Lake.: This holiday home rental outside of Olean is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 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 games in this rental home to help you unwind.

How many holiday rentals are there in Olean?

With 6 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.