A river winding through a green landscape with a town in the background.

Holiday Homes in Olean

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Olean holiday homes

A kitchen with wooden cabinets, a stove, a microwave, and a dining area with a table and chairs.

1. WOW! OleanGrt PriceEntire house! 4 bedrooms 2.5 baths 30 mins to Ellicotville

WOW! OleanGrt PriceEntire house! 4 bedrooms 2.5 baths 30 mins to Ellicotville
Olean
9.6 out of 10, Exceptional, (41 reviews)
"Great location with plenty of stores and restaurant choices nearby. House was warm and cozy. "
United States
John C.
The price is €291
includes taxes & fees
13 Oct - 14 Oct
WOW! OleanGrt PriceEntire house! 4 bedrooms 2.5 baths 30 mins to Ellicotville
A sign with the name 'WILDFLOWER' in a landscaped area with a stone wall, various plants, and a building in the background.

2. Quiet & Cozy Condo. Cool A/C & streaming. Walk to town & Holiday Valley

Quiet & Cozy Condo. Cool A/C & streaming. Walk to town & Holiday Valley
Ellicottville
9.6 out of 10, Exceptional, (34 reviews)
"Wonderful condo! Great location, perfectly described with lots of amenities not listed. Easy check in. Stacey is a great host and we look forward to staying again! Great off season value too. So nice to just relax but also lots to do!"
United States
Anonymous traveller
The price is €281
includes taxes & fees
11 Nov - 12 Nov
Quiet & Cozy Condo. Cool A/C & streaming. Walk to town & Holiday Valley
A covered porch with wicker furniture, a small table with a plant, and a view of a green landscape.

3. Shinglehouse. Pa. 2bdrm 2 bath stargaze nr Cherry Springs!

Shinglehouse. Pa. 2bdrm 2 bath stargaze nr Cherry Springs!
Shinglehouse
9.2 out of 10, Wonderful, (10 reviews)
"This is our second stay here. We truly enjoy this house and its location. Its always clean and welcoming. Its truly a slice of heaven and sure peaceful. "
United States
Jonathan B.
The price is €297
includes taxes & fees
13 Oct - 14 Oct
Shinglehouse. Pa. 2bdrm 2 bath stargaze nr Cherry Springs!
A kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a ceiling fan.

4. Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home

Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
Smethport
9.6 out of 10, Exceptional, (15 reviews)
"Cozy is a great way to describe this house. We felt right at home when we checked in."
United States
Carissa C.
The price is €206
includes taxes & fees
26 Oct - 27 Oct
Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
Room

5. 5-bedroom Home in Ellicottville view of Holiday Valley

5-bedroom Home in Ellicottville view of Holiday Valley
Ellicottville
The price is €638
includes taxes & fees
15 Oct - 16 Oct
5-bedroom Home in Ellicottville view of Holiday Valley
A row of blue houses with balconies by a calm pond, surrounded by greenery and a clear sky.

6. Across from Holiday Valley, sleeps 8, entire TH, walk to VLG, CLEAN, updated

Across from Holiday Valley, sleeps 8, entire TH, walk to VLG, CLEAN, updated
Ellicottville
9.8 out of 10, Exceptional, (63 reviews)
"Cute place, very clean, great location!"
United States
Marissa S.
The price is €353
includes taxes & fees
25 Oct - 26 Oct
Across from Holiday Valley, sleeps 8, entire TH, walk to VLG, CLEAN, updated
A two-story building with a covered porch and a staircase leading to the upper level.

7. Lincoln Boutique Motel- Lower Room #6

Lincoln Boutique Motel- Lower Room #6
Ellicottville
8.8 out of 10, Excellent, (3 reviews)
" Place is small but very nice and has everything you need for a night or two. Walking distance to the slopes and attached to a fun restaurant / bar "
United States
Andrea K.
Lincoln Boutique Motel- Lower Room #6
An outdoor patio with a grill, a table, and a view of a grassy field and hills.

8. New! Ideal location! Walk to Town! Family Fun! Mountain/Park Views! Pet Friendly

New! Ideal location! Walk to Town! Family Fun! Mountain/Park Views! Pet Friendly
Ellicottville
9.2 out of 10, Wonderful, (55 reviews)
"This house is very cozy and close to everything!"
United States
Kathleen L.
The price is €286
includes taxes & fees
15 Oct - 16 Oct
New! Ideal location! Walk to Town! Family Fun! Mountain/Park Views! Pet Friendly
A spacious living room with a fireplace, a television mounted above it, and a kitchen in the background.

9. Walkable and Pet friendly. Book your ski getaway now!

Walkable and Pet friendly. Book your ski getaway now!
Ellicottville
10.0 out of 10, Exceptional, (46 reviews)
"Great spot to stay for a ski weekend. The hosts were wonderful, and did their best to assist us to have a great stay. "
Canada
Francesca R.
The price is €398
includes taxes & fees
12 Nov - 13 Nov
Walkable and Pet friendly. Book your ski getaway now!
A living room with a fireplace, a sofa, a coffee table, a television, and a ceiling fan.

10. SPACIOUS TOWNHOME, GREAT SLOPE VIEWS - PERFECT FOR YOUR OUTDOOR GETAWAY!

SPACIOUS TOWNHOME, GREAT SLOPE VIEWS - PERFECT FOR YOUR OUTDOOR GETAWAY!
Ellicottville
10.0 out of 10, Exceptional, (73 reviews)
"Second time staying, absolutely beautiful place and great support and communication from host!"
United States
Kylie H.
SPACIOUS TOWNHOME, GREAT SLOPE VIEWS - PERFECT FOR YOUR OUTDOOR GETAWAY!
A bedroom with a stone wall, a fireplace, a bed with fluffy pillows, and a view of greenery through a glass door.

11. Walk to Holiday Valley, Family-sized House, Sleeps 9, Shuffleboard, 2 fireplaces

Walk to Holiday Valley, Family-sized House, Sleeps 9, Shuffleboard, 2 fireplaces
Ellicottville
10.0 out of 10, Exceptional, (13 reviews)
"House was great and supper accessible to slopes and town. "
United States
Michael M.
The price is €614
includes taxes & fees
20 Oct - 21 Oct
Walk to Holiday Valley, Family-sized House, Sleeps 9, Shuffleboard, 2 fireplaces
A modern kitchen with a large island, sliding glass doors to an outdoor area, and a wooden accent wall.

12. Village & Venture-Walkable Modern Comfort + Hot Tub

Village & Venture-Walkable Modern Comfort + Hot Tub
Ellicottville
10.0 out of 10, Exceptional, (6 reviews)
The price is €484
includes taxes & fees
26 Oct - 27 Oct
Village & Venture-Walkable Modern Comfort + Hot Tub
A dining area with a round table, chairs, and a hanging light fixture.

13. Ellicottville Ski House - Walk to Holiday Valley or Downtown

Ellicottville Ski House - Walk to Holiday Valley or Downtown
Ellicottville
10.0 out of 10, Exceptional, (1 review)
"Great location - close to Holiday Valley and downtown E-Ville. Home was comfortable and plenty of space to relax after a day on the slopes."
United States
Danielle L.
The price is €633
includes taxes & fees
31 Oct - 1 Nov
Ellicottville Ski House - Walk to Holiday Valley or Downtown
A dining area with a wooden table and chairs, a chandelier, and a view of a house through large windows.

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

-RARE- In-Village rental! 4-Bedrooms w HOT TUB & AC
Ellicottville
10.0 out of 10, Exceptional, (53 reviews)
"One night stay, but very easy and in a great location!"
United States
Dennis L.
The price is €538
includes taxes & fees
25 Oct - 26 Oct
-RARE- In-Village rental! 4-Bedrooms w HOT TUB & AC
A dining area with a hot tub, wooden ceiling, and a neon sign.

15. Best Location! NEW HOT TUB/Games/Bar/Yard/Outdoor Movie Theater/Etc!

Best Location! NEW HOT TUB/Games/Bar/Yard/Outdoor Movie Theater/Etc!
Ellicottville
10.0 out of 10, Exceptional, (49 reviews)
"We had a great stay. Perfect location and house was very clean"
United States
silene r.
The price is €493
includes taxes & fees
21 Oct - 22 Oct
Best Location! NEW HOT TUB/Games/Bar/Yard/Outdoor Movie Theater/Etc!
A bed with a wooden headboard, a blanket, and pillows. There are wall art pieces above the bed.

16. Après 4 All | Game Room, Hot Tub, Walkable

Après 4 All | Game Room, Hot Tub, Walkable
Ellicottville
10.0 out of 10, Exceptional, (5 reviews)
"Great house and description. Host communication was excellent and I appreciate all the help."
United States
Kevin W.
The price is €848
includes taxes & fees
28 Oct - 29 Oct
Après 4 All | Game Room, Hot Tub, Walkable
A living room with a fireplace, wooden flooring, a blue accent wall, and a patterned rug.

17. Gondola House | Hot tub, Arcade, Walkable Getaway, Fun Central! Game Room, Hot Tub, Steps to Village...

Gondola House | Hot tub, Arcade, Walkable Getaway, Fun Central! Game Room, Hot Tub, Steps to Village...
Ellicottville
10.0 out of 10, Exceptional, (21 reviews)
"Michelle was very accommodating and the property was lovely!"
United States
Larry P.
The price is €827
includes taxes & fees
27 Oct - 28 Oct
Gondola House | Hot tub, Arcade, Walkable Getaway, Fun Central! Game Room, Hot Tub, Steps to Village...
A living room with a fireplace, a ceiling fan, a television, and a sofa.

18. 2-bed full kitchen, Downtown Ellicottville-Loft 12

2-bed full kitchen, Downtown Ellicottville-Loft 12
Ellicottville
2-bed full kitchen, Downtown Ellicottville-Loft 12
★ Just a 5-minute stroll to shops, bars & restaurants + 5-minute drive to Ski

19. The Allen House: Chic & Colorful 3BR Downtown Ellicottville

The Allen House: Chic & Colorful 3BR Downtown Ellicottville
Ellicottville
8.8 out of 10, Excellent, (3 reviews)
"Great stay."
United States
Vince L.
The price is €423
includes taxes & fees
13 Oct - 14 Oct
The Allen House: Chic & Colorful 3BR Downtown Ellicottville
A modern kitchen with a central island, wooden chairs, and a dining table.

20. Walkable to Town, 3 Bed 2.5 Bath

Walkable to Town, 3 Bed 2.5 Bath
Ellicottville
10.0 out of 10, Exceptional, (69 reviews)
"It was extremely clean and very welcoming. The added amenities were great! Would definitely stay their again."
United States
Lynne C.
The price is €524
includes taxes & fees
25 Oct - 26 Oct
Walkable to Town, 3 Bed 2.5 Bath
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

Timberline Lodge

Timberline Lodge

10/10 Excellent
"We love staying here!"
Katelyn 2-night trip
Posted 2 hours ago
Timberline Lodge

Find out more about Olean

Olean Holiday Homes information

Number of reviews
415
Accommodation
167 Holiday Homes
Lowest Price
€206
Highest Price
€848