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

Olean Vacation Rentals

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Olean vacation rentals

Property grounds

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
$128 nightly
The price is $145
Sep 23 - Sep 24
Total with taxes and fees
Cozy Country Get Away Suite with a view of the Enchanted Mountains
Coffee/tea maker, fridge, microwave, oven

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.
$200 nightly
The price is $226
Sep 22 - Sep 23
Total with taxes and fees
Working farmette at converted warehouse in the Allegany Mountains.
Interior

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.
$224 nightly
The price is $253
Sep 22 - Sep 23
Total with taxes and fees
Serene 2-bedroom “Barndominium” apartment in Allegany perfect for your getaway
Smart TV

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
$170 nightly
The price is $191
Sep 21 - Sep 22
Total with taxes and fees
2-bedroom guest house in charming Cuba with WiFi
Coffee/tea maker, fridge, microwave, oven

5. 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.
$125 nightly
The price is $142
Sep 21 - Sep 22
Total with taxes and fees
Walk to Slopes & Town Studio
Interior

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.
$171 nightly
The price is $192
Sep 21 - Sep 22
Total with taxes and fees
Cozy Studio Near Holiday Valley & Village
Property grounds

7. 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
$205 nightly
The price is $232
Sep 21 - Sep 22
Total with taxes and fees
Quiet & Cozy Condo. Cool A/C & streaming. Walk to town & Holiday Valley
Interior

8. 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.
$251 nightly
The price is $282
Sep 23 - Sep 24
Total with taxes and fees
SnowPine Condo, Sleeps 8, A/C, Fireplace
Dining

9. 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.
$164 nightly
The price is $184
Sep 22 - Sep 23
Total with taxes and fees
Cozy Studio with Fireplace, King Bed, A/C
TV, fireplace, video games, stereo

10. 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.
$193 nightly
The price is $217
Sep 21 - Sep 22
Total with taxes and fees
SnowPine Condo, Sleeps 6, Patio, A/C
Property grounds

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, (72 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.
$228 nightly
The price is $257
Sep 21 - Sep 22
Total with taxes and fees
Stargazer-Magnificent Picturesque View-Dark Skies-Hiking-Biking-Wildlife-Pets
TV, fireplace

12. 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.
$252 nightly
The price is $284
Sep 21 - Sep 22
Total with taxes and fees
Holiday Valley Ski-In/Ski-Out Condo
Exterior

13. 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.
$222 nightly
The price is $250
Sep 27 - Sep 28
Total with taxes and fees
SnowPine Condo, King Bed, 2 Full Baths
Terrace/patio

14. 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.
$194 nightly
The price is $214
Sep 21 - Sep 22
Total with taxes and fees
Rustic Creekside Cabin
Outdoor dining

15. 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.
$181 nightly
The price is $204
Sep 22 - Sep 23
Total with taxes and fees
2-bedroom apartment in Village of Ellicottville perfect for your getaway.
Property grounds

16. 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 traveler
$229 nightly
The price is $258
Sep 21 - Sep 22
Total with taxes and fees
Ebb~n~Flow-Rustic-Solar Cabin-Heated-Hiking-Biking-Pond-Wildlife-Dark Skies-Pets
Exterior

17. Serenity Cabin:Authentic Rustic Forest Retreat/Mountain View Hiking/Pet friendly

Serenity Cabin:Authentic Rustic Forest Retreat/Mountain View Hiking/Pet friendly
Wellsville
9.6 out of 10, Exceptional, (67 reviews)
"What a great cabin. The view from the deck was amazing, and the cabin was truly secluded. We brought our dog, Kane, who also had an amazing time running up and down the slope of the property. They had everything we needed, and we enjoyed our trip. I came for the stars in the dark sky, and they did not disappoint. We will definitely stay again when we are in the area. "
United States
BARBARA F.
$252 nightly
The price is $284
Sep 21 - Sep 22
Total with taxes and fees
Serenity Cabin:Authentic Rustic Forest Retreat/Mountain View Hiking/Pet friendly
Microwave, oven, stovetop, dishwasher

18. 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.
$209 nightly
The price is $231
Sep 22 - Sep 23
Total with taxes and fees
Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
WiFi, bed sheets

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

Ski In/Out Condo with King Bed, Fireplace & Patio
Great Valley
$154 nightly
The price is $174
Sep 21 - Sep 22
Total with taxes and fees
Ski In/Out Condo with King Bed, Fireplace & Patio
Property grounds

20. 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.
$201 nightly
The price is $227
Sep 23 - Sep 24
Total with taxes and fees
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views
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

Timberline Lodge

Timberline Lodge

8/10 Good
"Absolutely loved the ski wing and being separate from everyone else. Our own hot tub was awesome. One thing I'd recommend is hooks outside to hang towels and wet suits on. The mirror inside the fence was a little odd and the inside could've used a deeper clean lots of spiders and dust and musty smell but otherwise great. Looking forward to our next stay"
Lori 2-night trip
Posted 1 hour ago
Timberline Lodge

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 $145 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.