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Top Holiday Rentals in Olean

Exterior
Cozy Country Get Away Suite with a view of the Enchanted Mountains
10.0 out of 10, Exceptional, (4)
"It was quiet and peaceful. Very cozy and would definitely stay again. "
The price is £117
includes taxes & fees
4 May - 5 May
Cozy Country Get Away Suite with a view of the Enchanted Mountains
Smart TV, fireplace, books
Modern cottage located in 250 private acres Pond Fishing Hiking Fire Pit
10.0 out of 10, Exceptional, (69)
"Adorable, well equipped property, lovely grounds, owner, kindly let me switch weekends with very little notice. Very much appreciated for a much needed family getaway. Thank you for a great stay!"
Modern cottage located in 250 private acres Pond Fishing Hiking Fire Pit
View from property
Beautiful 6 bedroom Ellicottville Chalet
10.0 out of 10, Exceptional, (34)
"We had a great time, large home, plenty of room for multiple families, short drive to town and slopes! Would definitely recommend."
Beautiful 6 bedroom Ellicottville Chalet
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Property grounds
New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥
10.0 out of 10, Exceptional, (27)
"This place was perfect for our large group. Enough space for the kids to play and an area for parents to hang out too. The host went above with the extras. The beds are comfy and the home was clean. We will be going back."
New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥
Aerial view
Adorable village farmhouse; perfect for spring and summer break!
10.0 out of 10, Exceptional, (1)
"The furnishings are solid and comfortable with lovely, cozy accessories including a basket of throw blankets for chilling evenings. The bedding is some of the most comfortable I’ve slept in on my travels. Convenient to town and the grocery store, so eating out and stocking the house with snacks and breakfast items is a breeze. This is a relatively new listing, so I asked about certain kitchen items/appliances before I came and Kristie was very helpful in answering questions and even brought...
Adorable village farmhouse; perfect for spring and summer break!
Property grounds
Beautiful chalet on 5 acres - 2 min to Village!👌 Hot-Tub, Sauna, Fire Pit🔥
10.0 out of 10, Exceptional, (45)
"The house is great. No problems whatsoever. Would definitely stay here again. Thank you."
Beautiful chalet on 5 acres - 2 min to Village!👌 Hot-Tub, Sauna, Fire Pit🔥
TV, fireplace
Holiday Valley Ski-In/Ski-Out Condo
10.0 out of 10, Exceptional, (19)
"Cute condo! We had a great stay! Unfortunately, it rained the entire day we planned to ski, but we had a blast playing board games! The hosts were accommodating for a later departure Sunday, since it snowed overnight, and we could ski for a few hours. Z"
The price is £234
includes taxes & fees
6 May - 7 May
Holiday Valley Ski-In/Ski-Out Condo
Fridge, microwave, oven, stovetop
Charming Farmhouse, including barn filled with horses and livestock
10.0 out of 10, Exceptional, (22)
"My family and I stayed with this host during the 2024 solar eclipse (which happened to be my daughter’s birthday)! We had an absolutely fantastic day. My daughters and their cousins loved going to the barn and visiting the animals – especially the barn cats! The hosts have really thought of everything. Traveling with a five year-old and a two year-old is never easy, but all the thoughtful family touches some much needed help during our trip. Thank you again, we would 100% recommend this property...
Charming Farmhouse, including barn filled with horses and livestock
Property grounds
New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥
10.0 out of 10, Exceptional, (49)
"Views can't be beat from the living room. Amazingly comfortable for our group of 9 adults. Plenty of amenities to accommodate a large group. Quiet, cozy, and a short 10 minute drive to the nearby town and slopes. Beds were very comfortable!"
New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥
Microwave, oven, stovetop, dishwasher
Charming Modern Victorian in the Village of EVL
10.0 out of 10, Exceptional, (24)
"Girls weekend trip - the house is beautiful! Very, very clean! Stocked with anything & everything you need. Close to town, about a 10min walk. Corey was wonderful to work with; very kind & always quick to respond. You will not go wrong at this place :)"
Charming Modern Victorian in the Village of EVL
Property grounds
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views
10.0 out of 10, Exceptional, (56)
"Nice little place!"
The price is £176
includes taxes & fees
28 May - 29 May
Updated & Modern w/ King Bed ~ Pet Friendly ~ Sleeps 4 ~ Beautiful views
Fridge, microwave, oven, stovetop
Spacious 8 Bdrm Chalet set up for entertaining!
10.0 out of 10, Exceptional, (5)
"Our family of 16 spent our Christmas here and it was one of best celebrations. The cabin was perfect, and we had plenty of room to spread out."
Spacious 8 Bdrm Chalet set up for entertaining!
Property grounds
COME REST AT THE NEST! Year round, water front home close to Ellicottville!
10.0 out of 10, Exceptional, (50)
"If you want to escape the bustle of daily life and go somewhere out of the way of the world to rejuvenate, this is your place. You will have the perfect host. The “Nest” is CLEAN, well appointed and full of thoughtful amenities—kitchen fully stocked with everything you need. We enjoyed the indoor and outdoor fireplaces, relaxing on the deck, grass and dock. The beds are comfortable and extra soft blankets are everywhere. There were loving touches around every corner, including a vase of fresh...
The price is £217
includes taxes & fees
6 May - 7 May
COME REST AT THE NEST! Year round, water front home close to Ellicottville!
Fridge, microwave, oven, stovetop
Renovated 3 bed, 2 bath condo, scenic views, king bed, patio with grill, AC
10.0 out of 10, Exceptional, (50)
"The place was well kept, in a perfect location and decently priced! We very mch enjoyed our little family getaway! We would happily return another time! - notes: I would suggest tea towels get packed- it was really the only thing missing and important for washing up, especially with a family and dishes."
The price is £178
includes taxes & fees
5 May - 6 May
Renovated 3 bed, 2 bath condo, scenic views, king bed, patio with grill, AC
Property grounds
All-Season ski chalet in Ellicottville, NY, outdoor hot tub with stunning views!
9.8 out of 10, Exceptional, (209)
"Every year we plan a trip to Ellicottville to get a few days of skiing in. This year we had a mixed group of families with kids ranging from 15 to 6. This house had the perfect set up with lots of sleeping options, common space, and plenty of fun for the kids between the games, PS3, pool table, pac man arcade, and campfire. The hot tub was also nice after skiing all day. This is the second property we have stayed at of the owners. They are absolutely wonderful. Their properties are always...
All-Season ski chalet in Ellicottville, NY, outdoor hot tub with stunning views!
Property grounds
Charming Log Cabin on Private Pond Nestled in Woods.
9.8 out of 10, Exceptional, (304)
"The property was a wonderful place to get away and relax. Our dogs were able to run off leash for their first time. They swam in the pond and we hiked in the woods behind the cabin every morning. My wife and I had coffee while enjoying the great view, we made smore's in the firepit and grilled on several occasions. The nearby town Ellicottville was slow paced and had some very enjoyable restaurants (winery, brewery, and Dina's), Niagara falls was close by. Overall the property was fantastic and...
Charming Log Cabin on Private Pond Nestled in Woods.
View from property
Best location! Large home with fire pit just steps to downtown Ellicottville
9.8 out of 10, Exceptional, (147)
"Comfortable house to spread out in. Easy walk to town center."
Best location! Large home with fire pit just steps to downtown Ellicottville
Property grounds
Large home near Holiday Valley, outdoor swimming pool & hot tub!
9.8 out of 10, Exceptional, (138)
"We love the home and the ability to have a bit of privacy with our own suites. Have a wonderful stay and enjoyed our visit to the Falls."
Large home near Holiday Valley, outdoor swimming pool & hot tub!
Living area | Smart TV
Renovated 2 bed, 1 bath condo, scenic views, king bed, patio with grill, AC
9.8 out of 10, Exceptional, (50)
"We really enjoyed our stay. Booking and check in were easy, all via the vrbo app. The place was as advertised, clean, and comfy. The WiFi wasn’t working, but a quick message to the owner and we figured out the power strip for the router and modem had come loose, probably during cleaning. Once plugged in everything worked great! The one downside was no snow for skiing, so we went to Niagara Falls. Would book again!"
The price is £140
includes taxes & fees
7 May - 8 May
Renovated 2 bed, 1 bath condo, scenic views, king bed, patio with grill, AC
Aerial view
Renovated 2 bed, 1 bath condo, scenic views, king bed, patio with grill, AC
9.8 out of 10, Exceptional, (47)
"The owner was very helpful with quick responses. The place was small, but very cozy and quiet. The place had everything we needed for a quick relaxing getaway. The only downside was there were alot of steps to get in and out of the place and unfortunately, I aways over pack, which meant more trips for my husband. But once inside it was very sweet. The nearby town had nice restuarants and some shopping."
The price is £141
includes taxes & fees
9 May - 10 May
Renovated 2 bed, 1 bath condo, scenic views, king bed, patio with grill, AC
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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.

Olean Holiday Rental Travel Info

Other types of properties in Olean you may be interested in

Exterior
Hampton Inn & Suites Olean
2.5 star property
9.4 out of 10, Exceptional, (187)
"There was an odor in the room. Musty smell. "
The price is £126
includes taxes & fees
30 May - 31 May
Hampton Inn & Suites Olean
Standard Room, 2 Queen Beds | Premium bedding, in-room safe, desk, iron/ironing board
Holiday Inn Express Olean, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, (589)
"Very spacious room. The bed was very comfortable. Nice big and clean bathroom. Breakfast options were also pretty good. Would stay here again. "
The price is £106
includes taxes & fees
16 May - 17 May
Holiday Inn Express Olean, an IHG Hotel
Exterior
Fairfield Inn & Suites by Marriott Olean
2.5 star property
9.0 out of 10, Wonderful, (364)
"Perfect "
The price is £116
includes taxes & fees
2 Jun - 3 Jun
Fairfield Inn & Suites by Marriott Olean
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.

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, apart-hotels, 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 £117 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 in Olean close to Cutco-Ka-Bar Visitors Center, 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 7 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 enjoy the outdoors, whereas family-friendly attractions include Cutco-Ka-Bar Visitors Center. 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.

Recent reviews of Olean properties
Expedia verified reviews