Olean Vacation Rentals

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Vacation Rentals in Olean

Our top choices for Olean vacation rentals

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

9.6 out of 10, Exceptional, (15)
"I loved staying here and would def come again. "
The price is CA $111
CA $203 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Country Get Away Suite with a view of the Enchanted Mountains

One of a kind Treehouse on the Genesee River

9.0 out of 10, Wonderful, (39)
"this was my second stay i enjoy it so much! And i only live 5 miles away, the location is so differnt you would never know! The owners are quick to make sure i enjoy my experiance! And its always very clean!"
One of a kind Treehouse on the Genesee River

Ellicottville all-Season chalet

9.8 out of 10, Exceptional, (252)
"Loved the house, had a great time. "
Ellicottville all-Season chalet

Charming Log Cabin on Private Pond Nestled in Woods Near Holiday Valley Resort

10.0 out of 10, Exceptional, (347)
"The cabin and property were exactly what we were expecting. Enjoyed the serene setting and comfortable cabin. "
Charming Log Cabin on Private Pond Nestled in Woods Near Holiday Valley Resort

Come and enjoy some peace and quiet at the Pumpkin hollow Inn

9.8 out of 10, Exceptional, (133)
"Nice and quiet little get a way. Would recommend to anyone looking for a breather from everyday life. "
Come and enjoy some peace and quiet at the Pumpkin hollow Inn

Cozy 2 bedroom cabin on a 20 acre lake

10.0 out of 10, Exceptional, (12)
"Great place to get away, quiet and peaceful, enjoyable spot for individuals or familiar. "
Cozy 2 bedroom cabin on a 20 acre lake

Cozy, upgraded, pet friendly cabin, formerly Cuba Lake Vintage Duck House.

9.8 out of 10, Exceptional, (15)
"Great spot, friendly owner, lot's of fun things to do, just an overall great time! "
Cozy, upgraded, pet friendly cabin, formerly Cuba Lake Vintage Duck House.

Rustic Creekside Cabin

9.8 out of 10, Exceptional, (70)
"We loved this place. For being rustic, everything was well thought of to make this a relaxing and refreshing experience. When leaving, we felt a bittersweet feeling. We enjoyed the wildlife and taking walks. A lovely area! The one thing it needed...cows on the hillside with bells around their necks! As I said in the beginning, we LOVED this place! "
The price is CA $203
CA $301 total
includes taxes & fees
Sep 8 - Sep 9
Rustic Creekside Cabin

Cool & Quiet Condo–Walk to Town, AC & Balcony. Across street from Holiday Resort

2.0 star property
9.4 out of 10, Exceptional, (13)
"Very nice property! Very clean, comfortable and well stocked. Would stay again! "
The price is CA $166
CA $358 total
includes taxes & fees
Sep 14 - Sep 15
Cool & Quiet Condo–Walk to Town, AC & Balcony. Across street from Holiday Resort

Quality in Town, Hot Tub Great Reviews!CLEAN! Comfy Beds Photo wall Game room

9.8 out of 10, Exceptional, (151)
"Myself, husband, dad, 3 children (including the grad), her significant other, and best friend all stayed in elicottville so that we were a reasonable distance away from her college. Accommodations were great and well suited for our group"
The price is CA $275
CA $980 total
includes taxes & fees
Oct 6 - Oct 7
Quality in Town, Hot Tub Great Reviews!CLEAN! Comfy Beds Photo wall Game room

Quaint townhome with WiFi in charming Ellicottville

8.0 out of 10, Very good, (1)
"Summertime girls weekend getaway to Holiday Valley/Ellicottville. We adored the little town and all there is to do in the area. The townhome is in a great location, close to everything. Host very responsive. Beautiful unit with all of the necessary amenities. Well stocked kitchen. Plenty of sleeping space. The only drawback was no AC. Was a bit uncomfortable but manageable with some fans. The lower level bedrooms were cool enough but a bit musty probably from all the recent rain. Overall a...
The price is CA $275
CA $534 total
includes taxes & fees
Sep 8 - Sep 9
Quaint townhome with WiFi in charming Ellicottville

-RARE- In-Village rental! 4-Bedrooms w HOT TUB & AC

9.8 out of 10, Exceptional, (38)
"Fantastic property, very welcoming - everything we needed was onsite and then some! Great location!"
The price is CA $343
CA $711 total
includes taxes & fees
Sep 22 - Sep 23
-RARE- In-Village rental! 4-Bedrooms w HOT TUB & AC

Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville

9.8 out of 10, Exceptional, (6)
"Great place, super friendly with awesome communication, thank you! "
The price is CA $180
CA $305 total
includes taxes & fees
Sep 8 - Sep 9
Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville

Breathtaking views, modern container design

2.0 star property
10.0 out of 10, Exceptional, (2)
"Quiet, beautiful, great views of the stars, sunset and sunrise! Would love to go back."
The price is CA $195
CA $446 total
includes taxes & fees
Sep 10 - Sep 11
Breathtaking views, modern container design

Across from Holiday Valley, sleeps 10, entire TH, walk to VLG, CLEAN, updated

9.8 out of 10, Exceptional, (53)
"Great location, great communication with owner, great snow! Perfect size for family of 4. "
The price is CA $275
CA $570 total
includes taxes & fees
Sep 15 - Sep 16
Across from Holiday Valley, sleeps 10, entire TH, walk to VLG, CLEAN, updated

Charming 2-bedroom condo in superb Ellicottville with AC, WiFi

9.8 out of 10, Exceptional, (7)
"It was very clean and quiet and lots of space. Will definitely be back for another stay. "
The price is CA $304
CA $447 total
includes taxes & fees
Sep 8 - Sep 9
Charming 2-bedroom condo in superb Ellicottville with AC, WiFi

King Bed, A/C, Pickleball, Patio w/ Grill

9.8 out of 10, Exceptional, (65)
"This place was really nice, definitely staying again."
The price is CA $115
CA $274 total
includes taxes & fees
Sep 9 - Sep 10
King Bed, A/C, Pickleball, Patio w/ Grill

Large Ski Home + Pool & Hot Tub

9.8 out of 10, Exceptional, (161)
"Had a few friends come down for the weekend - was a great place to host and hang out. "
Large Ski Home + Pool & Hot Tub

Serenity - Private, secluded cabin-excellant scenic view/sunset, hiking, pond

9.6 out of 10, Exceptional, (62)
"Great location, great view off the deck. Maintained hiking trails was a great feature."
The price is CA $194
CA $327 total
includes taxes & fees
Sep 28 - Sep 29
Serenity - Private, secluded cabin-excellant scenic view/sunset, hiking, pond

UNIQUE Log Style Cozy Ski Chalet - Walking Distance To Town - Pets Welcome

10.0 out of 10, Exceptional, (62)
"Next time we come out to ski I know where we will be staying! Everything was perfect! Thank you to our hosts what a wonderful place to stay "
The price is CA $386
CA $811 total
includes taxes & fees
Sep 8 - Sep 9
UNIQUE Log Style Cozy Ski Chalet - Walking Distance To Town - Pets Welcome
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

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Olean vacation rentals we have selected for you start as low as CA $111 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 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. 

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?

Stunning Chalet with Breathtaking Holimont Views – Perfect for Families: This vacation home rental near Olean offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a coffee maker, so you can cook with friends or family.

How many vacation rentals are there in Olean?

With 5 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.