Olean Holiday Rentals

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Our top choices for Olean holiday rentals

Business or Pleasure - a perfect and cozy get-away!

Business or Pleasure - a perfect and cozy get-away!
Jefferson City
9.6 out of 10, Exceptional, (32 reviews)
"Perfect place to stay for my trip"
United States
Joshua B.
The price is AU$237
includes taxes & fees
26 May - 27 May
Business or Pleasure - a perfect and cozy get-away!

Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary

Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary
Jefferson City
10.0 out of 10, Exceptional, (50 reviews)
"Excellent stay! Charming house. Great location. Perfect for an extended stay."
United States
Ellen R.
The price is AU$411
includes taxes & fees
25 May - 26 May
Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary

The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace
Jefferson City
10.0 out of 10, Exceptional, (35 reviews)
"Very spacious, has everything a big family needs for a place to stay. Will definitely consider it next time again."
United States
ALVIN
The price is AU$449
includes taxes & fees
10 June - 11 June
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

Charming cabin with WiFi and AC in delightful Eldon

Charming cabin with WiFi and AC in delightful Eldon
Eldon
9.4 out of 10, Exceptional, (12 reviews)
"The cabin was nice was clean and wonderful views"
United States
JEREMY
The price is AU$225
includes taxes & fees
26 May - 27 May
Charming cabin with WiFi and AC in delightful Eldon

Historic 4-bedroom pet friendly rental close to downtown.

Historic 4-bedroom pet friendly rental close to downtown.
Jefferson City
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful! Extremely child & pet friendly. We traveled with our 5 children and could not have asked for a more perfect place. Highly recommended. "
United States
Jacquelyn
The price is AU$627
includes taxes & fees
28 May - 29 May
Historic 4-bedroom pet friendly rental close to downtown.

“Clabe” one of the 5 Tiny Cabins on the Osage River

“Clabe” one of the 5 Tiny Cabins on the Osage River
Tuscumbia
10.0 out of 10, Exceptional, (2 reviews)
"It was a great quiet place to get away for a weekend."
United States
Kyle B.
The price is AU$249
includes taxes & fees
26 May - 27 May
“Clabe” one of the 5 Tiny Cabins on the Osage River

Nearby Trails: 1BR Apartment w/ W & D

Nearby Trails: 1BR Apartment w/ W & D
3.0 star property
Lake Ozark
The price is AU$357
includes taxes & fees
25 May - 26 May
Nearby Trails: 1BR Apartment w/ W & D

Lake of the Ozarks North Shore Cabin on the quiet side of lake.

Lake of the Ozarks North Shore Cabin on the quiet side of lake.
Rocky Mount
10.0 out of 10, Exceptional, (6 reviews)
"Great place. Very clean and everything you could need. Would definitely stay again!"
United States
Josh L.
The price is AU$217
includes taxes & fees
25 May - 26 May
Lake of the Ozarks North Shore Cabin on the quiet side of lake.

Treetop Village The Forest Den #100-Lakefront 3BD/3BA/Pools/Deck/Dock/Grill-6PP

Treetop Village The Forest Den #100-Lakefront 3BD/3BA/Pools/Deck/Dock/Grill-6PP
Village of Four Seasons
8.0 out of 10, Very good, (1 review)
The price is AU$444
includes taxes & fees
25 May - 26 May
Treetop Village The Forest Den #100-Lakefront 3BD/3BA/Pools/Deck/Dock/Grill-6PP

Newly remodeled updated condo,12x32 Boat slip, wi-Fi Internet cable TV, pwc slip

Newly remodeled updated condo,12x32 Boat slip, wi-Fi Internet cable TV, pwc slip
Lake Ozark
10.0 out of 10, Exceptional, (84 reviews)
"Great place!"
United States
J.D. L.
The price is AU$556
includes taxes & fees
25 May - 26 May
Newly remodeled updated condo,12x32 Boat slip, wi-Fi Internet cable TV, pwc slip

Hideaway in the Trees-#30-Lakefront/2BD/3BA/Pools/Grill/Dock-4PP

Hideaway in the Trees-#30-Lakefront/2BD/3BA/Pools/Grill/Dock-4PP
Village of Four Seasons
9.4 out of 10, Exceptional, (8 reviews)
"The host was communicative, the house was in a great spot, and was very unique. We will definitely come back!"
United States
Sabrena M.
The price is AU$373
includes taxes & fees
25 May - 26 May
Hideaway in the Trees-#30-Lakefront/2BD/3BA/Pools/Grill/Dock-4PP

Cedar Sanctuary #17-2BD/2BA/Pools/Grill/Dock-4PP

Cedar Sanctuary #17-2BD/2BA/Pools/Grill/Dock-4PP
Village of Four Seasons
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great!"
United States
Jeffrey B.
The price is AU$396
includes taxes & fees
25 May - 26 May
Cedar Sanctuary #17-2BD/2BA/Pools/Grill/Dock-4PP

SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort

SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort
Lake Ozark
9.4 out of 10, Exceptional, (13 reviews)
"Photos and description were accurate. Great value. "
United States
micah
The price is AU$657
includes taxes & fees
26 May - 27 May
SALE! Lakefront | 4 Pools | Dock | Sauna | +Resort

Cozy Cabin on the Lake! Sleeps 2 @ Jacks Shack!

Cozy Cabin on the Lake! Sleeps 2 @ Jacks Shack!
Osage Beach
9.8 out of 10, Exceptional, (7 reviews)
"Comfortable and cozy!Right on the water and able to walk to backwater jacks ! "
United States
Jeff G.
The price is AU$415
includes taxes & fees
26 May - 27 May
Cozy Cabin on the Lake! Sleeps 2 @ Jacks Shack!

Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor
Osage Beach
10.0 out of 10, Exceptional, (98 reviews)
"She was great wonderful suggestions we love the view close to mamy places to enjoy "
United States
Jeannie B.
The price is AU$412
includes taxes & fees
27 May - 28 May
Stylish Lakefront, King Bed Suite, Sunset View, Pool, Boat Slip, PrivateTopFloor

3MM, fully remolded, main channel lakefront with pool

3MM, fully remolded, main channel lakefront with pool
Lake Ozark
10.0 out of 10, Exceptional, (46 reviews)
"Great weekend getaway. "
United States
Lawrence H.
The price is AU$439
includes taxes & fees
27 May - 28 May
3MM, fully remolded, main channel lakefront with pool

Main Channel View! Cozy Studio on Bagnell Dam Blvd

Main Channel View! Cozy Studio on Bagnell Dam Blvd
3.0 star property
Lake Ozark
The price is AU$442
includes taxes & fees
25 May - 26 May
Main Channel View! Cozy Studio on Bagnell Dam Blvd

Wheelhouse: Lakefront 2BD/3BA/Deck/Pool/Pet Friendly-6PP

Wheelhouse: Lakefront 2BD/3BA/Deck/Pool/Pet Friendly-6PP
Lake Ozark
9.2 out of 10, Wonderful, (11 reviews)
"Cute little cozy place with perfect for 2 couples. Would definitely stay again!!"
United States
Brian H.
The price is AU$367
includes taxes & fees
26 May - 27 May
Wheelhouse: Lakefront 2BD/3BA/Deck/Pool/Pet Friendly-6PP

Beach Cabin #6, Private/Shared Beach - Cabin #6

Beach Cabin #6, Private/Shared Beach - Cabin #6
Lake Ozark
Beach Cabin #6, Private/Shared Beach - Cabin #6

Cozy, Yet Spacious Condo, Hot Tub/Indoor Pool, Close to Everything

Cozy, Yet Spacious Condo, Hot Tub/Indoor Pool, Close to Everything
Lake Ozark
9.4 out of 10, Exceptional, (18 reviews)
"Very nice accommodations. Really enjoyed our stay"
United States
Edward G.
The price is AU$386
includes taxes & fees
26 May - 27 May
Cozy, Yet Spacious Condo, Hot Tub/Indoor Pool, Close to Everything
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

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, 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 favourite 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 depend 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 AU$249 per night. Entering your travel dates in the search wizard might find you 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 close to the most popular sights in Olean, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Olean has to offer?

Cozy lake in front of the home: This holiday home rental outside of Olean is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Olean?

While exploring the area, visit family-friendly sights like Willmore Lodge, or get outside and enjoy nature at Lick Branch Cove. In the wider area, you’ll find Osage National Golf Course and Lake of the Ozarks and Bagnell Dam Viewpoint.

What’s a holiday rental in Olean like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Olean. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.