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

Olean Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Olean vacation 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

Cozy Country Get Away Suite with a view of the Enchanted Mountains
Olean
9.0 out of 10, Wonderful, (33 reviews)
"Perfect little spot. So peaceful & homey."
United States
Sean
The price is ￥12,610
￥23,144 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Country Get Away Suite with a view of the Enchanted Mountains
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

WOW! OleanGrt PriceEntire house! 4 bedrooms 2.5 baths 30 mins to Ellicotville
Olean
9.6 out of 10, Exceptional, (41 reviews)
"Great location with plenty of stores and restaurant choices nearby. House was warm and cozy. "
United States
John C.
The price is ￥17,711
￥42,609 total
includes taxes & fees
Oct 7 - Oct 8
WOW! OleanGrt PriceEntire house! 4 bedrooms 2.5 baths 30 mins to Ellicotville
A modern kitchen with dark cabinetry, a white microwave, a stove, and a sink.

3. 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, (66 reviews)
"Loved the place very spacious."
United States
Philip M.
The price is ￥25,976
￥37,180 total
includes taxes & fees
Oct 4 - Oct 5
Working farmette at converted warehouse in the Allegany Mountains.
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

Serene 2-bedroom “Barndominium” apartment in Allegany perfect for your getaway
Allegany
10.0 out of 10, Exceptional, (8 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 ￥29,125
￥41,806 total
includes taxes & fees
Oct 4 - Oct 5
Serene 2-bedroom “Barndominium” apartment in Allegany perfect for your getaway
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

2-bedroom guest house in charming Cuba with WiFi
Cuba
10.0 out of 10, Exceptional, (14 reviews)
"Great place to stay "
United States
Beth B.
The price is ￥18,104
￥30,108 total
includes taxes & fees
Oct 19 - Oct 20
2-bedroom guest house in charming Cuba with WiFi
A compact kitchen with white cabinets, a stainless steel dishwasher, a microwave, and a wooden floor.

6. 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 ￥24,402
￥31,488 total
includes taxes & fees
Oct 19 - Oct 20
Walk to Slopes & Town Studio
Living area

7. The Allen House

The Allen House
3.5 star property
Ellicottville
The price is ￥41,291
￥63,975 total
includes taxes & fees
Nov 1 - Nov 2
The Allen House
A sign with the name 'WILDFLOWER' in a landscaped area with a stone wall, various plants, and a building in the background.

8. 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 traveler
The price is ￥19,679
￥41,272 total
includes taxes & fees
Oct 4 - Oct 5
Quiet & Cozy Condo. Cool A/C & streaming. Walk to town & Holiday Valley
Interior

9. 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 ￥16,845
￥33,260 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Studio Near Holiday Valley & Village
A cafe interior with a counter, a chalkboard menu, and a coffee machine.

10. Huge 3 Bedroom apartment in Bolivar NY

Huge 3 Bedroom apartment in Bolivar NY
Bolivar
9.0 out of 10, Wonderful, (4 reviews)
"Great place to stay while visiting family in the area. Nice cafe downstairs where Lily made some amazing coffee drinks while we got checked in."
United States
Matt B.
The price is ￥15,444
￥31,719 total
includes taxes & fees
Oct 14 - Oct 15
Huge 3 Bedroom apartment in Bolivar NY
An outdoor seating area with a fire pit surrounded by stone seating and tables, set against a stone building with a balcony.

11. 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 ￥20,458
￥38,233 total
includes taxes & fees
Oct 4 - Oct 5
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views
A covered porch with wicker furniture, a small table with a plant, and a view of a green landscape.

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

Shinglehouse. Pa. 2bdrm 2 bath stargaze nr Cherry Springs!
Shinglehouse
9.2 out of 10, Wonderful, (10 reviews)
"This is our second stay here. We truly enjoy this house and its location. Its always clean and welcoming. Its truly a slice of heaven and sure peaceful. "
United States
Jonathan B.
The price is ￥25,787
￥52,440 total
includes taxes & fees
Oct 2 - Oct 3
Shinglehouse. Pa. 2bdrm 2 bath stargaze nr Cherry Springs!
Exterior

13. SnowPine Condo, King Bed, 2 Full Baths

SnowPine Condo, King Bed, 2 Full Baths
Ellicottville
9.8 out of 10, Exceptional, (25 reviews)
"Great location to the slopes. "
United States
Michelle L.
The price is ￥19,679
￥40,732 total
includes taxes & fees
Oct 6 - Oct 7
SnowPine Condo, King Bed, 2 Full Baths
A grassy field with a pond, a rainbow, and a forested hill in the background.

14. 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, (73 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 ￥23,615
￥43,039 total
includes taxes & fees
Oct 4 - Oct 5
Stargazer-Magnificent Picturesque View-Dark Skies-Hiking-Biking-Wildlife-Pets
A kitchen with a built-in sink, a coffee maker, and a range hood.

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

Ski In/Out Condo with King Bed, Fireplace & Patio
Great Valley
10.0 out of 10, Exceptional, (1 review)
"Very clean and cozy! Our friends rebooked it for February! Highly recommend staying here!!"
United States
Lisa B.
The price is ￥23,457
￥44,830 total
includes taxes & fees
Nov 1 - Nov 2
Ski In/Out Condo with King Bed, Fireplace & Patio
Room

16. Gorgeous 5-bedroom house in welcoming Ellicottville perfect for families

Gorgeous 5-bedroom house in welcoming Ellicottville perfect for families
Ellicottville
The price is ￥42,506
￥110,829 total
includes taxes & fees
Oct 4 - Oct 5
Gorgeous 5-bedroom house in welcoming Ellicottville perfect for families
A cozy room with a wooden ceiling, a chandelier, a dining table with a bench, a fireplace, and a large window with curtains.

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

Cozy Studio with Fireplace, King Bed, A/C
Ellicottville
10.0 out of 10, Exceptional, (18 reviews)
"Perfect location for a ski weekend, and we loved the wood-burning fireplace!"
United States
Kim V.
The price is ￥14,484
￥30,236 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Studio with Fireplace, King Bed, A/C
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

Holiday Valley Ski-In/Ski-Out Condo
Great Valley
10.0 out of 10, Exceptional, (74 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 ￥18,734
￥43,762 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Valley Ski-In/Ski-Out Condo
A modern living room with a spiral staircase, a fireplace, a sofa, and a television.

19. 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 ￥23,929
￥44,289 total
includes taxes & fees
Nov 1 - Nov 2
SnowPine Condo, Sleeps 6, Patio, A/C
A living room with a stone fireplace, a flat-screen TV, a red armchair, and a spiral staircase.

20. SnowPine Condo, Sleeps 8, A/C, Fireplace

SnowPine Condo, Sleeps 8, A/C, Fireplace
Ellicottville
10.0 out of 10, Exceptional, (75 reviews)
"Great appliances, very clean and great spot to hop on the slopes! "
United States
Emma W.
The price is ￥19,994
￥43,223 total
includes taxes & fees
Oct 5 - Oct 6
SnowPine Condo, Sleeps 8, A/C, Fireplace
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

Seneca Allegany Resort & Casino

Seneca Allegany Resort & Casino

8/10 Good
"Overall, quite nice, but I went on Tuesday and the spa salon was closed that day. They also had a restaurant in a bar that were closed. That would’ve been nice to test out. I will return."
Kurt 1-night trip
Posted 2 hours ago
Seneca Allegany Resort & Casino

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
  • Use the map to find apartments and other holiday homes in the Olean neighbourhood you prefer
  • 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?

Fantastic lake house on the south shore of Cuba Lake.: This vacation home rental near Olean is located on a lake and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Olean?

With 6 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.