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Featured Cottages in Olean and around

Charming cottage, great for families, pet-friendly
Fridge, microwave, oven, stovetop

Charming cottage, great for families, pet-friendly

9.6 out of 10, Exceptional, (164)
"The house was absolutely perfect for our trip! The house had all kinds of fun stuff to use including the hot tub which was amazing after walking all day at the fall festival. We would definitely come back. "
Charming cottage, great for families, pet-friendly
Modern cottage located in 250 private acres Pond Fishing Hiking Fire Pit
Smart TV, fireplace, books

Modern cottage located in 250 private acres Pond Fishing Hiking Fire Pit

10.0 out of 10, Exceptional, (95)
"Quiet, only nature sounds when on trails and near house. Pretty private, beautiful scenery, hiking & fishing. Stargazing is incredible here, LOOK UP! My girlfriend and I stayed at David’s cottage to unplug and unwind for our anniversary. While we found ourselves using the tv as Penn state disappointed us against OSU, that was the only disappointment during the wonderful weekend we had. The immediate back yard had a great view of the hillside. The house was well stocked for our long weekend,...
Modern cottage located in 250 private acres Pond Fishing Hiking Fire Pit
Lovely Cottage That Is Completely New With All The Luxuries You Would Want!
Property grounds

Lovely Cottage That Is Completely New With All The Luxuries You Would Want!

10.0 out of 10, Exceptional, (118)
"This is just what we needed. Quiet and peaceful. Thanks Bette"
Lovely Cottage That Is Completely New With All The Luxuries You Would Want!
Cozy Country Get Away Suite with a view of the Enchanted Mountains
Exterior detail

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

10.0 out of 10, Exceptional, (10)
"Nice people cute little spot didn’t stay long but was a great stay "
The price is €140
includes taxes & fees
5 Dec - 6 Dec
Cozy Country Get Away Suite with a view of the Enchanted Mountains
Lime Lake Cottage w/ Lakefront Deck & Dock!
Terrace/patio

Lime Lake Cottage w/ Lakefront Deck & Dock!

9.6 out of 10, Exceptional, (5)
"Family member also on lake so we enjoyed water sports with them."
Lime Lake Cottage w/ Lakefront Deck & Dock!
Stargazer... magnificent, picturesque view
Smart TV, stereo

Stargazer... magnificent, picturesque view

9.8 out of 10, Exceptional, (49)
"This gem of a cottage has absolutely stunning views. We booked our stay during a new moon in hopes of seeing the Milky Way at night. Unfortunately, it rained. Thankfully the cottage is 10 minutes from Wellsville so we had a good evening there and a warm, cozy place to spend the night. The bed was very comfortable. Even though it is five hours from our home, we hope to return when the weather is conducive for stargazing."
The price is €221
includes taxes & fees
5 Dec - 6 Dec
Stargazer... magnificent, picturesque view
Private Cottage at Saisons Inn in Ellicottville, New York
Outdoor pool, a heated pool

Private Cottage at Saisons Inn in Ellicottville, New York

9.8 out of 10, Exceptional, (16)
"We had a great stay! We would stay again with JY and Deborah:) They were great and very accommodating!"
Private Cottage at Saisons Inn in Ellicottville, New York
Cozy, upgraded, pet friendly cabin, formerly Cuba Lake Vintage Duck House.
Terrace/patio

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

9.8 out of 10, Exceptional, (9)
"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.
Updated Cuba Lake Retreat. Pontoon Available
Interior

Updated Cuba Lake Retreat. Pontoon Available

10.0 out of 10, Exceptional, (1)
"Very comfortable and quiet loved it"
Updated Cuba Lake Retreat. Pontoon Available
Salamanca Home ~ 9 Mi to Holiday Valley Resort
House (2 Bedrooms) | Interior

Salamanca Home ~ 9 Mi to Holiday Valley Resort

3.0 star property
10.0 out of 10, Exceptional, (1)
"The stay was amazing, the host was wonderful. Property in Great shape. Can't wait to go again."
Salamanca Home ~ 9 Mi to Holiday Valley Resort
Charming Historic Home ~ 1 Mi to Dtwn Olean!
House (4 Bedrooms) | Private kitchen

Charming Historic Home ~ 1 Mi to Dtwn Olean!

3.0 star property
Charming Historic Home ~ 1 Mi to Dtwn Olean!
Nationally Registered Usonian Cottage at Lynn Hall by FLW's Fallingwater Builder
Smart TV, fireplace, books, stereo

Nationally Registered Usonian Cottage at Lynn Hall by FLW's Fallingwater Builder

10.0 out of 10, Exceptional, (1)
"The owners have done an amazing job restoring this fabulous piece of organic modernism architecture to its fullest. Not only is it authentic, it is tasteful and high-end in every aspect - all the amenities are quality. We felt immersed in luxury yet comfortable and relaxed. The owners’ tour is not to be missed, informative, delicious appetizers and wine, and added a deeper dimension to our stay. Cannot recommend this stay enough if you want to spoil yourself while out in the Pennsylvania Wilds!"
Nationally Registered Usonian Cottage at Lynn Hall by FLW's Fallingwater Builder
Mountain-view Home in Great Valley w/ Large Yard!
House (2 Bedrooms) | Private kitchen

Mountain-view Home in Great Valley w/ Large Yard!

3.0 star property
8.0 out of 10, Very good, (1)
"We liked the house, however we were not able to enjoy the outside because of the rain all weekend. It was situated close to the area we were interested in visiting and we were able to enjoy the casino and shopping.Thank you for having us."
Mountain-view Home in Great Valley w/ Large Yard!
Lime Lake Cottage w/ Lakefront Deck & Dock!
Interior

Lime Lake Cottage w/ Lakefront Deck & Dock!

3.0 star property
Lime Lake Cottage w/ Lakefront Deck & Dock!
Entire Chalet! Hot Tub! Vaulted Timber Ceiling! AC
Private kitchen

Entire Chalet! Hot Tub! Vaulted Timber Ceiling! AC

Entire Chalet! Hot Tub! Vaulted Timber Ceiling! AC
Pet-friendly Franklinville Farmhouse w/ Sunroom!
House (3 Bedrooms) | Private kitchen

Pet-friendly Franklinville Farmhouse w/ Sunroom!

3.0 star property
Pet-friendly Franklinville Farmhouse w/ Sunroom!
Great Valley Home w/ On-site Pond, 7 Mi to Skiing!
Interior

Great Valley Home w/ On-site Pond, 7 Mi to Skiing!

3.0 star property
Great Valley Home w/ On-site Pond, 7 Mi to Skiing!
Spacious Victorian Home 1/4 Mi to Holiday Valley!
Outdoor dining

Spacious Victorian Home 1/4 Mi to Holiday Valley!

3.0 star property
Spacious Victorian Home 1/4 Mi to Holiday Valley!
Mountaintop Ellicottville Home: 7 Mi to Ski Resort
House (5 Bedrooms) | Private kitchen

Mountaintop Ellicottville Home: 7 Mi to Ski Resort

3.0 star property
Mountaintop Ellicottville Home: 7 Mi to Ski Resort
Peaceful Allegany Home, Walk to Sbu!
Interior

Peaceful Allegany Home, Walk to Sbu!

3.0 star property
Peaceful Allegany Home, Walk to Sbu!
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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Other property types in Olean

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

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

10.0 out of 10, Exceptional, (10)
"Nice people cute little spot didn’t stay long but was a great stay "
The price is €140
includes taxes & fees
5 Dec - 6 Dec
Cozy Country Get Away Suite with a view of the Enchanted Mountains
Rustic Creekside Cabin
Terrace/patio

Rustic Creekside Cabin

9.8 out of 10, Exceptional, (64)
"It was fun and exciting cooking by a fire and on top of a wood stove "
The price is €210
includes taxes & fees
4 Jan - 5 Jan 2025
Rustic Creekside Cabin
Book your ski getaway! Walk to town!
Property grounds

Book your ski getaway! Walk to town!

10.0 out of 10, Exceptional, (14)
"Nice place, great neighborhood within walking distance to the shops and restaurants."
Book your ski getaway! Walk to town!
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.

Frequently asked questions

Why book your cottage in Olean with Expedia?
Expedia has some superb cottages in Olean, so get ready for an unforgettable holiday on nature’s doorstep. If you have a fixed budget, select how much you’d like to spend and your preferred property star rating. Or, make use of our filters to search for cottages with a kitchen or a pool. We’ll help you find the right place whatever your escape looks like.
How can I find cheap cottages in Olean?
With Expedia’s handy filter tool, locating cheap cottages in Olean couldn’t be simpler. To view accommodation that are very pocket friendly, narrow your search results by amenities, budget and star rating.
What is there to do in Olean near my cottage?
If you’d like to discover the sights of Olean, don’t miss Gargoyle Park. It’s a hit among locals and visitors alike.