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Olean Holiday Apartments

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50 rentals in Olean.
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Fishing Getaway, holiday rental in Olean

Fishing Getaway

1 bedroom
1 bathroom
Sleeps 4
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Enchanted home in center of Olean, holiday rental in Olean

Enchanted home in center of Olean

4 bedrooms
3 bathrooms
Sleeps 8
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Olean Ny right in town 100 night, holiday rental in Olean

Olean Ny right in town 100 night

4 bedrooms
2 bathrooms
Sleeps 11
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Ellicottville cabin - 4 miles from Holiday Valley, holiday rental in Olean

Ellicottville cabin - 4 miles from Holiday Valley

3 bedrooms
2 bathrooms
Sleeps 6
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Across from Holiday Valley, holiday rental in Olean

Across from Holiday Valley

1 bedroom
1 bathroom
Sleeps 5
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Allegany State Park Rental in the Forest, holiday rental in Olean

Allegany State Park Rental in the Forest

3 bedrooms
2 bathrooms
Sleeps 6
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Lovely Cottage That Is Completely New With All The Luxuries You Would Want!, holiday rental in Olean

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

2 bedrooms
2 bathrooms
Sleeps 7
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Charming Lakefront Ranch, holiday rental in Olean

Charming Lakefront Ranch

3 bedrooms
2 bathrooms
Sleeps 6
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Brand New Build! The Gorgeous Chardonnay Chalet, holiday rental in Olean

Brand New Build! The Gorgeous Chardonnay Chalet

4 bedrooms
3 bathrooms
Sleeps 10
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Spacious Charming Country Home for All Seasons -Golf-Ski-Relax, holiday rental in Olean

Spacious Charming Country Home for All Seasons -Golf-Ski-Relax

4 bedrooms
4 bathrooms
Sleeps 13
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Relax and unwind in our cozy townhome!, holiday rental in Olean

Relax and unwind in our cozy townhome!

3 bedrooms
2 bathrooms
Sleeps 10
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Renovated ski-in/ski-out condo at Holiday Valley, holiday rental in Olean

Renovated ski-in/ski-out condo at Holiday Valley

2 bedrooms
1 bathroom
Sleeps 8
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Beautiful and spacious 4 Bdrm Ski Chalet With Breathtaking Mountain View., holiday rental in Olean

Beautiful and spacious 4 Bdrm Ski Chalet With Breathtaking Mountain View.

4 bedrooms
3 bathrooms
Sleeps 15
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Updated townhome - Walking distance to Holiday Valley Ski Slopes!, holiday rental in Olean

Updated townhome - Walking distance to Holiday Valley Ski Slopes!

4 bedrooms
2 bathrooms
Sleeps 12
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SPRING  is where you need to stay!, holiday rental in Olean

SPRING is where you need to stay!

3 bedrooms
2 bathrooms
Sleeps 8
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5 Bedroom Mansion within minutes to local attractions & shopping, holiday rental in Olean

5 Bedroom Mansion within minutes to local attractions & shopping

5 bedrooms
5 bathrooms
Sleeps 10
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IF YOUR LOOKING FOR PEACE AND QUIET THIS IS THE PLACE, holiday rental in Olean

IF YOUR LOOKING FOR PEACE AND QUIET THIS IS THE PLACE

2 bedrooms
1 bathroom
Sleeps 5
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Updated ski-in/ski-out condo Holiday Valley, holiday rental in Olean

Updated ski-in/ski-out condo Holiday Valley

1 bedroom
1 bathroom
Sleeps 7
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Spectacular Ski Townhouse across from Holiday Valley, holiday rental in Olean

Spectacular Ski Townhouse across from Holiday Valley

4 bedrooms
4 bathrooms
Sleeps 14
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Last minute availability! Stylish, Modern & Walkable to Holiday Valley, holiday rental in Olean

Last minute availability! Stylish, Modern & Walkable to Holiday Valley

3 bedrooms
3 bathrooms
Sleeps 13
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Cozy, 3 BR 2 bath across from Holiday Valley, free ski shuttle, 1 mile to town, holiday rental in Olean

Cozy, 3 BR 2 bath across from Holiday Valley, free ski shuttle, 1 mile to town

3 bedrooms
2 bathrooms
Sleeps 8
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Luxury Townhome across from Holiday Valley, holiday rental in Olean

Luxury Townhome across from Holiday Valley

4 bedrooms
4 bathrooms
Sleeps 11
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Newly renovated ski-in/out condo Holiday Valley, holiday rental in Olean

Newly renovated ski-in/out condo Holiday Valley

3 bedrooms
2 bathrooms
Sleeps 8
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Walk to the slopes or The Village- Perfect Location, holiday rental in Olean

Walk to the slopes or The Village- Perfect Location

3 bedrooms
1 bathroom
Sleeps 6
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Great Spot on the Lake!, holiday rental in Olean

Great Spot on the Lake!

3 bedrooms
2 bathrooms
Sleeps 8
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Home away from Home! Great location in between the Village  and  Holiday Valley, holiday rental in Olean

Home away from Home! Great location in between the Village and Holiday Valley

5 bedrooms
3 bathrooms
Sleeps 10
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Family getaway in beautiful Ellicottville!, holiday rental in Olean

Family getaway in beautiful Ellicottville!

1 bedroom
1 bathroom
Sleeps 6
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Special Ski Getaway 8 mins to Ski Resorts Holiday Valley & Holimont Skiing, holiday rental in Olean

Special Ski Getaway 8 mins to Ski Resorts Holiday Valley & Holimont Skiing

3 bedrooms
2 bathrooms
Sleeps 14
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Charming Woodland Log Cabin on Private Pond, holiday rental in Olean

Charming Woodland Log Cabin on Private Pond

1 bedroom
1 bathroom
Sleeps 4
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The Royal Suite has a combination of Elegance and Comfort., holiday rental in Olean

The Royal Suite has a combination of Elegance and Comfort.

3 bedrooms
2 bathrooms
Sleeps 8
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Ski lodge in Ellicotville, holiday rental in Olean

Ski lodge in Ellicotville

3 bedrooms
2 bathrooms
Sleeps 8
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1920s Cuba Lake Cottage with 4 bedrooms and one bathroom, large yard, and dock., holiday rental in Olean

1920s Cuba Lake Cottage with 4 bedrooms and one bathroom, large yard, and dock.

4 bedrooms
1 bathroom
Sleeps 7
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Ground floor, cozy and private, holiday rental in Olean

Ground floor, cozy and private

0 bedrooms
1 bathroom
Sleeps 4
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Bradford Flatiron. Iconic. Charming. Downtown., holiday rental in Olean

Bradford Flatiron. Iconic. Charming. Downtown.

2 bedrooms
2 bathrooms
Sleeps 4
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Fox Ridge 204 - An Updated Townhouse with Spectacular Views of the Slopes!, holiday rental in Olean

Fox Ridge 204 - An Updated Townhouse with Spectacular Views of the Slopes!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Mountaintop Ellicottville Home w/Deck Near Skiing!, holiday rental in Olean

Mountaintop Ellicottville Home w/Deck Near Skiing!

5 bedrooms
4 bathrooms
Sleeps 10
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The Montana.  Remote,  private setting .  No hidden fees!, holiday rental in Olean

The Montana. Remote, private setting . No hidden fees!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Crown Penthouse Suite with gorgeous scenic views though close to everything, holiday rental in Olean

The Crown Penthouse Suite with gorgeous scenic views though close to everything

3 bedrooms
2 bathrooms
Sleeps 9
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Great Valley Mtn. House on 30 Acres w/Pond & Grill, holiday rental in Olean

Great Valley Mtn. House on 30 Acres w/Pond & Grill

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ellicottville Condo - Walk to Holiday Valley!, holiday rental in Olean

Ellicottville Condo - Walk to Holiday Valley!

1 bedroom
1 bathroom
Sleeps 4
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Wildflower 85, holiday rental in Olean

Wildflower 85

2 bedrooms
2 bathrooms
Sleeps 8
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Wildflower 54, holiday rental in Olean

Wildflower 54

1 bedroom
1 bathroom
Sleeps 4
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Fox Ridge 204, holiday rental in Olean

Fox Ridge 204

4 bedrooms
3 bathrooms
Sleeps 10
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Alpine Meadows 30, holiday rental in Olean

Alpine Meadows 30

2 bedrooms
2 bathrooms
Sleeps 9
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Deer Valley, holiday rental in Olean

Deer Valley

5 bedrooms
3 bathrooms
Sleeps 12
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Myers Chalet, holiday rental in Olean

Myers Chalet

3 bedrooms
3 bathrooms
Sleeps 10
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Chalet Rosche -Best location to experience Ellicottville - Luxury Fox Ridge home, holiday rental in Olean

Chalet Rosche -Best location to experience Ellicottville - Luxury Fox Ridge home

3 bedrooms
2 bathrooms
Sleeps 7
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NEW! Ski-In Ski-Out Condo at Holiday Valley Resort, holiday rental in Olean

NEW! Ski-In Ski-Out Condo at Holiday Valley Resort

4 bedrooms
2 bathrooms
Sleeps 10
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Smokey Valley Lodge, holiday rental in Olean

Smokey Valley Lodge

2 bedrooms
2 bathrooms
Sleeps 8
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Spacious Victorian Home 1/4 Mi to Holiday Valley!, holiday rental in Olean

Spacious Victorian Home 1/4 Mi to Holiday Valley!

8 bedrooms
4 bathrooms
Sleeps 10
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