Search Vacation Homes in Olean

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Olean

Lakefront Treetop Village 2BD/3 BA/Deck/Pool/Four Seasons Amenities-6PP

8.8 out of 10, Excellent, (3)
"Great location, nice amenities and close to many activities. I always travel with my pups and they were comfortable as well ."
$281 nightly
The price is $291
Aug 14 - Aug 15
Total includes taxes and fees
Lakefront Treetop Village 2BD/3 BA/Deck/Pool/Four Seasons Amenities-6PP

Lakefront Treehouse Treetop Village 2 Bed/3BA/Pools/Pickleball/Dock-6-8PP

8.0 out of 10, Very Good, (2)
"Aside from a misunderstanding housekeeping, it wasn't bad. Three different individuals with the housekeeping department came by and tried to enter the house a day before check out. Two of the three did not speak English, so communication with them was nonexistent. The 3rd individual, insisted that we should have been gone, even though it was a day prior to our scheduled check-out date. Miscommunication between the booking personnel and housekeeping was not good. We spent our last afternoon, into...
$283 nightly
The price is $293
Aug 24 - Aug 25
Total includes taxes and fees
Lakefront Treehouse Treetop Village 2 Bed/3BA/Pools/Pickleball/Dock-6-8PP

Osage Beach Lake House w/ Views! Private dock w/ boat slip in neighborhood cove!

9.6 out of 10, Exceptional, (8)
"My friends and I had the most amazing stay! Being right off the lake makes going to any of the hot spots in town so easy. Beautiful property with a beautiful interior. Couldn’t have asked for a better stay. We will definitely book again as soon we’re back in Osage Beach :)"
Osage Beach Lake House w/ Views! Private dock w/ boat slip in neighborhood cove!

Lakefront Treehouse Treetop Village 2 Bed/3BA/Pools/Pickleball/Dock-6-8PP

8.0 out of 10, Very Good, (2)
"Communication was a little difficulty at times but overall we loved our time here!"
$281 nightly
The price is $291
Aug 17 - Aug 18
Total includes taxes and fees
Lakefront Treehouse Treetop Village 2 Bed/3BA/Pools/Pickleball/Dock-6-8PP

Treetop Village51-3Bed/3Bath/Pools/Dock/Pickleball/Fitness Center-6-8PP-Four Seasons Area

$311 nightly
The price is $321
Aug 12 - Aug 13
Total includes taxes and fees
Treetop Village51-3Bed/3Bath/Pools/Dock/Pickleball/Fitness Center-6-8PP-Four Seasons Area

2BD, 1BA Home. 5-10 Minutes to ANYWHERE in JCMO!

10.0 out of 10, Exceptional, (30)
"The place was clean and comfortable. Provided a nice place to stay while we were in town."
2BD, 1BA Home. 5-10 Minutes to ANYWHERE in JCMO!

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

2.0 star property
10.0 out of 10, Exceptional, (19)
"It was very nice"
$301 nightly
The price is $315
Aug 24 - Aug 25
Total includes taxes and fees
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

SUPER CLEAN! private dock & lrg outdoor living w/ bar - big cove w kayak & SUP

10.0 out of 10, Exceptional, (130)
"This property was perfect for our little getaway. It exceeded all of our expectations!"
SUPER CLEAN! private dock & lrg outdoor living w/ bar - big cove w kayak & SUP

Treetop Village13-2Bed/2Bath/Pools/Dock/Pickleball/Fitness Center-6-8PP-Four Seasons Area

7.0 out of 10, Good, (2)
"It is a great property and a great location. The beds were not very comfortable. The tvs were outdated but they had cable. "
$281 nightly
The price is $291
Aug 12 - Aug 13
Total includes taxes and fees
Treetop Village13-2Bed/2Bath/Pools/Dock/Pickleball/Fitness Center-6-8PP-Four Seasons Area

HUGE DOCK on a Beautiful Lake Property at the Lake of the Ozarks

9.4 out of 10, Exceptional, (54)
"House had all we needed for the week. Owner was very helpful and available. The dock was such a cool space to spend time outside, fishing, drinking and watching tv. We stayed during springbreak but my guess is this place is even better on the summer. "
HUGE DOCK on a Beautiful Lake Property at the Lake of the Ozarks

Treetop Village60-3Bed/3Bath/Pools/Dock/Pickleball/Lakefront/Lakeview/Fitness Center-6-8PP

9.0 out of 10, Wonderful, (2)
"Overall, great place to relax among the trees and wildlife in a quiet cove off the main channel. Pool was great, clean and swimming with the view of the lake.Coffee make didn't work and the staff handled that right away. Super friendly. Would stay here again!"
$325 nightly
The price is $336
Aug 12 - Aug 13
Total includes taxes and fees
Treetop Village60-3Bed/3Bath/Pools/Dock/Pickleball/Lakefront/Lakeview/Fitness Center-6-8PP

Cozy lake in front of the home

9.6 out of 10, Exceptional, (92)
"It was a great location for a weekend getaway."
Cozy lake in front of the home

Lakefront Home with Game Room, Firepits & Gazebo at 3MM

9.0 out of 10, Wonderful, (2)
"House was amazing to stay in. It had everything we needed inside. It was a bit disappointing that there wasn’t actual water access. You can’t jump off that dock because there are giant rocks about two foot deep and there is no ladder to get down or back up from the water. We also couldn’t get picked up from a rented boat at our place and had to drive to the nearest marina. "
Lakefront Home with Game Room, Firepits & Gazebo at 3MM

Fishermen, Side by side riders! 3bed 2bath with xtra Parking! Close to lake&loop

10.0 out of 10, Exceptional, (1)
"Great place to stay! Can’t say enough good things about it, had everything we needed. Super clean! The yard was great to sit outside in the evening by a fire host was very responsive to any questions. Beds were comfy. We had a great time. "
Fishermen, Side by side riders! 3bed 2bath with xtra Parking! Close to lake&loop

Voted #1 by USA Today!

9.8 out of 10, Exceptional, (181)
"Second year in a row and we find everything beautiful "
$1,747 nightly
The price is $1,912
Aug 17 - Aug 18
Total includes taxes and fees
Voted #1 by USA Today!

Gardenia Getaway - Man cave, pool, hot tub! NEW !

8.0 out of 10, Very Good, (4)
"Very clean! Perfect set up."
$3,610 nightly
The price is $3,871
Aug 26 - Aug 27
Total includes taxes and fees
Gardenia Getaway - Man cave, pool, hot tub! NEW !

Lakefront Getaway at Lake of the Ozarks – Your Perfect Summer Escape!

9.8 out of 10, Exceptional, (183)
"Everything was as described. Lots of room and easy access to the lake. Would definitely stay again!"
$1,043 nightly
The price is $1,141
Aug 17 - Aug 18
Total includes taxes and fees
Lakefront Getaway at Lake of the Ozarks – Your Perfect Summer Escape!

Ken's Kabin a nostalgic Lake of the Ozarks cabin with a fantastic view!

9.4 out of 10, Exceptional, (69)
"We love staying here. We've met the family both times we've stayed there. They are so nice. It is a great spot. I just wish it was a little bigger. It is really only for 3 people. A couch with a bed it would be great. "
Ken's Kabin a nostalgic Lake of the Ozarks cabin with a fantastic view!

Luxury Lakefront HGTV Home-3Bed/3Bath/Dock/Firepit/Sleeps-14PP

9.0 out of 10, Wonderful, (2)
"The Chalet is decorated very nicely, bedrooms & baths were very comfortable. Patio & dock were where we spent most of our time. They are a bit dilapidated need to be repaired very soon, but we enjoyed them nevertheless swimming and fishing were both two thumbs up."
$468 nightly
The price is $487
Sep 7 - Sep 8
Total includes taxes and fees
Luxury Lakefront HGTV Home-3Bed/3Bath/Dock/Firepit/Sleeps-14PP

Lakefront dog-friendly home with lake views, firepit, dock, huge deck

8.8 out of 10, Excellent, (17)
"Completely recommend. Our family loved our stay and will absolutely be looking to return in the future. "
Lakefront dog-friendly home with lake views, firepit, dock, huge deck
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Olean Hotel Reviews