Olean Holiday Rentals from NZ$231: Search Short-Term Rentals

Q: 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.

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Our top choices for Olean holiday rentals

A pathway lined with candles leading to a cabin in a forest.

1. Cozy Country Get Away Suite with a view of the Enchanted Mountains

Olean

Sean

includes taxes & fees

3 Dec - 4 Dec

A kitchen with wooden cabinets, a stove, a microwave, and a dining area with a table and chairs.

2. WOW! OleanGrt PriceEntire house! 4 bedrooms 2.5 baths 30 mins to Ellicotville

Olean

John C.

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with dark cabinetry, a white microwave, a stove, and a sink.

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

Allegany

Virginia (Ginger) S.

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with dark cabinets, a microwave, a stove, and a refrigerator. There is a dining table with chairs and a sofa with a patterned throw pillow.

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

Allegany

Joseph M.

includes taxes & fees

3 Nov - 4 Nov

A living room with a flat-screen TV, a sofa, a coffee table, and a patterned rug.

5. 2-bedroom guest house in charming Cuba with WiFi

Cuba

Beth B.

includes taxes & fees

25 Nov - 26 Nov

A sign with the name 'WILDFLOWER' in a landscaped area with a stone wall, various plants, and a building in the background.

6. Quiet & Cozy Condo. Fireplace& Free Shuttle to HV. Walk to town & Holiday Valley

Ellicottville

Tina G.

includes taxes & fees

3 Nov - 4 Nov

A living room with a fireplace, a sofa, a coffee table, and a staircase with a geometric wall design.

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

Great Valley

Olivia C.

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a spiral staircase, a fireplace, a sofa, and a television.

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

Ellicottville

Shannon S.

includes taxes & fees

4 Nov - 5 Nov

9. SnowPine Condo, King Bed, Patio + Fireplace

Ellicottville

Michael V.

includes taxes & fees

5 Nov - 6 Nov

A cafe interior with a counter, a chalkboard menu, and a coffee machine.

10. Huge 3 Bedroom apartment in Bolivar NY

Bolivar

Matt B.

includes taxes & fees

3 Nov - 4 Nov

11. Cozy Studio Near Holiday Valley & Village

Ellicottville

"We had a fantastic stay at this condo in Ellicottville! The space was clean, comfortable, and thoughtfully set up for a great trip. We loved the cozy atmosphere and how easy it was to relax after a day out—whether we were exploring town or enjoying the area activities. The location felt convenient, and we appreciated the care taken with the details throughout the condo. Communication was quick and helpful, and check-in was smooth. We would absolutely stay here again and highly recommend it to...

Penny C.

includes taxes & fees

3 Nov - 4 Nov

A cozy room with a wooden ceiling, a chandelier, a dining table with a bench, a fireplace, and a large window with curtains.

12. Cozy Studio with Fireplace, King Bed, A/C

Ellicottville

Kim V.

includes taxes & fees

10 Nov - 11 Nov

13. SnowPine Condo, King Bed, 2 Full Baths

Ellicottville

Michelle L.

includes taxes & fees

3 Nov - 4 Nov

A covered porch with wicker furniture, a small table with a plant, and a view of a green landscape.

14. Shinglehouse. Pa. 2bdrm 2 bath stargaze nr Cherry Springs!

Shinglehouse

Jonathan B.

includes taxes & fees

3 Nov - 4 Nov

A living room with a fireplace, a sofa, a coffee table with books and remotes, and a TV mounted on the wall.

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

Great Valley

Lisa B.

includes taxes & fees

8 Nov - 9 Nov

A rustic log cabin with a porch, a fire pit, and a bench.

16. Rustic Creekside Cabin

Shinglehouse

Curt K.

includes taxes & fees

5 Nov - 6 Nov

An outdoor seating area with a fire pit surrounded by stone seating and tables, set against a stone building with a balcony.

17. Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views

Ellicottville

Lisa D.

includes taxes & fees

4 Nov - 5 Nov

A living room with a stone fireplace, a television mounted above it, and a spiral staircase leading to an upper level.

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

Great Valley

Chris B.

includes taxes & fees

3 Nov - 4 Nov

A black triangular cabin with a wooden door, a small porch, and a window.

19. Honest Abe Frame @ Sunrise

Ellicottville

PARTH

includes taxes & fees

3 Nov - 4 Nov

A wooden deck with a table and chairs, a blue umbrella, and a house in the background.

20. 2-bedroom apartment in Village of Ellicottville perfect for your getaway.

Ellicottville

Robert P.

includes taxes & fees

5 Nov - 6 Nov

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Top Olean Hotel Reviews

The Inn At Holiday Valley

10/10 Excellent

"Great service"

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

8/10 Good

"Loved the location in a beautiful rural area not far from town, which was very peaceful and quiet. Enjoyed the new deck, lovely nature setting, and lighted pathway with flickering lantern lights in the evening. Host was responsive to any of our questions. Could only stay a day, but could easily have stayed longer."

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$231 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.

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Check prices for these dates

Our top choices for Olean holiday rentals

1. Cozy Country Get Away Suite with a view of the Enchanted Mountains

2. WOW! OleanGrt PriceEntire house! 4 bedrooms 2.5 baths 30 mins to Ellicotville

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

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

5. 2-bedroom guest house in charming Cuba with WiFi

6. Quiet & Cozy Condo. Fireplace& Free Shuttle to HV. Walk to town & Holiday Valley

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

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

9. SnowPine Condo, King Bed, Patio + Fireplace

10. Huge 3 Bedroom apartment in Bolivar NY

11. Cozy Studio Near Holiday Valley & Village

12. Cozy Studio with Fireplace, King Bed, A/C

13. SnowPine Condo, King Bed, 2 Full Baths

14. Shinglehouse. Pa. 2bdrm 2 bath stargaze nr Cherry Springs!

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

16. Rustic Creekside Cabin

17. Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views

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

19. Honest Abe Frame @ Sunrise

20. 2-bedroom apartment in Village of Ellicottville perfect for your getaway.

Find holiday rentals that suit your style

Top Olean Hotel Reviews

The Inn At Holiday Valley

Holiday Inn Express Bradford by IHG

Fairfield Inn & Suites by Marriott Olean

Best Western Plus University Inn

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

Find out more about Olean

Frequently asked questions

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