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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (34 reviews)
"Perfect little spot. So peaceful & homey."
United States
Sean
$135 nightly
The price is $152
Oct 14 - Oct 15
Total with taxes and fees
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.
$240 nightly
The price is $271
Oct 6 - Oct 7
Total with taxes and fees
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.
$209 nightly
The price is $236
Oct 6 - Oct 7
Total with taxes and fees
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.
$235 nightly
The price is $266
Oct 6 - Oct 7
Total with taxes and fees
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.
$170 nightly
The price is $191
Oct 19 - Oct 20
Total with taxes and fees
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.
$174 nightly
The price is $197
Oct 13 - Oct 14
Total with taxes and fees
Walk to Slopes & Town Studio
Living area

7. The Allen House

The Allen House
3.5 star property
Ellicottville
$393 nightly
The price is $444
Nov 3 - Nov 4
Total with taxes and fees
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
$210 nightly
The price is $238
Oct 8 - Oct 9
Total with taxes and fees
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.
$178 nightly
The price is $200
Nov 4 - Nov 5
Total with taxes and fees
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.
$179 nightly
The price is $201
Oct 14 - Oct 15
Total with taxes and fees
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.
$215 nightly
The price is $243
Oct 6 - Oct 7
Total with taxes and fees
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.
$302 nightly
The price is $333
Oct 6 - Oct 7
Total with taxes and fees
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.
$229 nightly
The price is $258
Nov 3 - Nov 4
Total with taxes and fees
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.
$226 nightly
The price is $254
Oct 6 - Oct 7
Total with taxes and fees
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, (2 reviews)
"Very clean and cozy! Our friends rebooked it for February! Highly recommend staying here!!"
United States
Lisa B.
$252 nightly
The price is $285
Nov 1 - Nov 2
Total with taxes and fees
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
$623 nightly
The price is $704
Oct 8 - Oct 9
Total with taxes and fees
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.
$171 nightly
The price is $192
Oct 6 - Oct 7
Total with taxes and fees
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.
$246 nightly
The price is $278
Oct 26 - Oct 27
Total with taxes and fees
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.
$218 nightly
The price is $245
Nov 2 - Nov 3
Total with taxes and fees
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.
$242 nightly
The price is $272
Nov 3 - Nov 4
Total with taxes and fees
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

The Lincoln Boutique Motel

The Lincoln Boutique Motel

10/10 Excellent
"Property was really interesting. A lovingly restored motel. Modern finishes and comfortable beds… literally right at the foot of the mountain"
Brian 1-night trip
Posted 1 hour ago
The Lincoln Boutique Motel

Find out more about Olean

Everything you need to know about Olean vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Olean vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Olean vacation 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 low season months. For more hustle and bustle, you may prefer to visit Olean in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Olean rentals

At Expedia, we put the best Olean vacation 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 vacation.

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 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.