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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 NZ$483
includes taxes & fees
4 Oct - 5 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 NZ$422
includes taxes & fees
4 Oct - 5 Oct
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 NZ$625
includes taxes & fees
26 Oct - 27 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 NZ$406
includes taxes & fees
4 Oct - 5 Oct
Smitty's Cozy Corner in Smethport, PA. Spaciously 4-bedroom home
A row of blue houses with balconies by a calm pond, surrounded by greenery and a clear sky.

5. 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 NZ$690
includes taxes & fees
4 Oct - 5 Oct
Across from Holiday Valley, sleeps 8, entire TH, walk to VLG, CLEAN, updated
Room

6. Gorgeous 5-bedroom house in welcoming Ellicottville perfect for families

Gorgeous 5-bedroom house in welcoming Ellicottville perfect for families
Ellicottville
The price is NZ$1,210
includes taxes & fees
28 Oct - 29 Oct
Gorgeous 5-bedroom house in welcoming Ellicottville perfect for families
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.
The price is NZ$409
includes taxes & fees
5 Oct - 6 Oct
Lincoln Boutique Motel- Lower Room #6
A living room with a fireplace, a sofa, a coffee table, a television, and a ceiling fan.

8. 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.
The price is NZ$739
includes taxes & fees
12 Oct - 13 Oct
SPACIOUS TOWNHOME, GREAT SLOPE VIEWS - PERFECT FOR YOUR OUTDOOR GETAWAY!
An outdoor patio with a grill, a table, and a view of a grassy field and hills.

9. 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 NZ$551
includes taxes & fees
4 Oct - 5 Oct
New! Ideal location! Walk to Town! Family Fun! Mountain/Park Views! Pet Friendly
A staircase with white railings and wooden steps leading to a room with a gray sofa and a potted plant.

10. The Devereaux House in Ellicottville NY

The Devereaux House in Ellicottville NY
Ellicottville
10.0 out of 10, Exceptional, (3 reviews)
"Great place! "
United States
Cathleen B.
The price is NZ$754
includes taxes & fees
18 Oct - 19 Oct
The Devereaux House in Ellicottville NY
A spacious living room with a fireplace, a television mounted above it, and a kitchen in the background.

11. Walkable, Pet friendly, Farmhouse

Walkable, Pet friendly, Farmhouse
Ellicottville
10.0 out of 10, Exceptional, (45 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 NZ$637
includes taxes & fees
4 Oct - 5 Oct
Walkable, Pet friendly, Farmhouse
A dining area with a hot tub, wooden ceiling, and a neon sign.

12. 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, (48 reviews)
"We had a great stay. Perfect location and house was very clean"
United States
silene r.
The price is NZ$979
includes taxes & fees
27 Oct - 28 Oct
Best Location! NEW HOT TUB/Games/Bar/Yard/Outdoor Movie Theater/Etc!
A hot tub on a wooden deck with a view of a hilly landscape.

13. The Eagles Nest – Couples Escape - Hot Tub & Views!

The Eagles Nest – Couples Escape - Hot Tub & Views!
Ellicottville
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful place. Relaxing w nice amenities"
United States
Bennette D.
The price is NZ$1,109
includes taxes & fees
5 Oct - 6 Oct
The Eagles Nest – Couples Escape - Hot Tub & Views!
A modern kitchen with a large island, sliding glass doors to an outdoor area, and a wooden accent wall.

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

Village & Venture-Walkable Modern Comfort + Hot Tub
Ellicottville
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$1,055
includes taxes & fees
6 Oct - 7 Oct
Village & Venture-Walkable Modern Comfort + Hot Tub
A dining area with a round table, chairs, and a hanging light fixture.

15. Ellicottville Ski House

Ellicottville Ski House
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 NZ$1,265
includes taxes & fees
18 Oct - 19 Oct
Ellicottville Ski House
★ Just a 5-minute stroll to shops, bars & restaurants + 5-minute drive to Ski

16. 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 NZ$827
includes taxes & fees
5 Oct - 6 Oct
The Allen House: Chic & Colorful 3BR Downtown Ellicottville
A modern kitchen with white cabinets, stainless steel appliances, and pendant lighting.

17. NEWLY BUILT condo - premium features, game room, firepit, short walk to village

NEWLY BUILT condo - premium features, game room, firepit, short walk to village
Ellicottville
10.0 out of 10, Exceptional, (31 reviews)
"Second time staying here. Beautiful accommodations and close to town. "
United States
Beth B.
The price is NZ$1,198
includes taxes & fees
4 Oct - 5 Oct
NEWLY BUILT condo - premium features, game room, firepit, short walk to village
A modern kitchen with a central island, wooden chairs, and a dining table.

18. Walkable to Town, 3 Bed 2.5 Bath

Walkable to Town, 3 Bed 2.5 Bath
Ellicottville
10.0 out of 10, Exceptional, (68 reviews)
"Beautiful stay all around! "
United States
Annmarie T.
The price is NZ$1,105
includes taxes & fees
4 Oct - 5 Oct
Walkable to Town, 3 Bed 2.5 Bath
A dining area with a wooden table and chairs, a chandelier, and a view of a house through large windows.

19. -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 NZ$961
includes taxes & fees
27 Oct - 28 Oct
-RARE- In-Village rental! 4-Bedrooms w HOT TUB & AC
A bedroom with a stone wall, a fireplace, a bed with fluffy pillows, and a view of greenery through a glass door.

20. 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 NZ$1,313
includes taxes & fees
15 Oct - 16 Oct
Walk to Holiday Valley, Family-sized House, Sleeps 9, Shuffleboard, 2 fireplaces
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

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

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

8/10 Good
"Loved the location in a beautiful rural area not far from town, which was very peaceful and quiet. Enjoyed the new deck, lovely nature setting, and lighted pathway with flickering lantern lights in the evening. Host was responsive to any of our questions. Could only stay a day, but could easily have stayed longer."
Amy 1-night trip
Posted 6 hours ago
Cozy Country Get Away Suite with a view of the Enchanted Mountains

Find out more about Olean

Olean Holiday Homes information

Number of reviews
373
Accommodation
169 Holiday Homes
Lowest Price
NZ$406
Highest Price
NZ$1,313