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Olean Vacation Rentals

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

Fishing Getaway

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Enchanted home in center of Olean, vacation rental in Olean
Enchanted home in center of Olean, vacation rental in Olean
Enchanted home in center of Olean, vacation rental in Olean

Enchanted home in center of Olean

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Olean Ny whole house 4 bedrooms right in town 100 night, vacation rental in Olean
Olean Ny whole house 4 bedrooms right in town 100 night, vacation rental in Olean
Olean Ny whole house 4 bedrooms right in town 100 night, vacation rental in Olean

Olean Ny whole house 4 bedrooms right in town 100 night

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Ellicottville cabin - 4 miles from Holiday Valley, vacation rental in Olean
Ellicottville cabin - 4 miles from Holiday Valley, vacation rental in Olean
Ellicottville cabin - 4 miles from Holiday Valley, vacation rental in Olean

Ellicottville cabin - 4 miles from Holiday Valley

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

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Allegany State Park Rental in the Forest, vacation rental in Olean
Allegany State Park Rental in the Forest, vacation rental in Olean
Allegany State Park Rental in the Forest, vacation rental in Olean

Allegany State Park Rental in the Forest

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Lakefront Ranch, vacation rental in Olean
Charming Lakefront Ranch, vacation rental in Olean
Charming Lakefront Ranch, vacation rental in Olean

Charming Lakefront Ranch

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Charming Country Home for All Seasons -Golf-Ski-Relax, vacation rental in Olean
Spacious Charming Country Home for All Seasons -Golf-Ski-Relax, vacation rental in Olean
Spacious Charming Country Home for All Seasons -Golf-Ski-Relax, vacation rental in Olean

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Beautiful and spacious 4 Bdrm Ski Chalet With Breathtaking Mountain View.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Renovated ski-in/ski-out condo at Holiday Valley, vacation rental in Olean
Renovated ski-in/ski-out condo at Holiday Valley, vacation rental in Olean
Renovated ski-in/ski-out condo at Holiday Valley, vacation rental in Olean

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Save time - get the best Olean rentals sent straight to your email!
IF YOUR LOOKING FOR PEACE AND QUIET THIS IS THE PLACE, vacation rental in Olean
IF YOUR LOOKING FOR PEACE AND QUIET THIS IS THE PLACE, vacation rental in Olean
IF YOUR LOOKING FOR PEACE AND QUIET THIS IS THE PLACE, vacation rental in Olean

IF YOUR LOOKING FOR PEACE AND QUIET THIS IS THE PLACE

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Family getaway in beautiful Ellicottville!, vacation rental in Olean
Family getaway in beautiful Ellicottville!, vacation rental in Olean
Family getaway in beautiful Ellicottville!, vacation rental in Olean

Family getaway in beautiful Ellicottville!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Vintage Charm Cuba Lake Duck House Cabin with room for 3 and the doggie.

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Mountaintop Ellicottville Home w/Deck Near Skiing!, vacation rental in Olean
Mountaintop Ellicottville Home w/Deck Near Skiing!, vacation rental in Olean
Mountaintop Ellicottville Home w/Deck Near Skiing!, vacation rental in Olean

Mountaintop Ellicottville Home w/Deck Near Skiing!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Entire Townhouse sleeps 10, steps from slopes! Short walk to village, vacation rental in Olean
Entire Townhouse sleeps 10, steps from slopes! Short walk to village, vacation rental in Olean
Entire Townhouse sleeps 10, steps from slopes! Short walk to village, vacation rental in Olean

Entire Townhouse sleeps 10, steps from slopes! Short walk to village

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Updated ski-in/ski-out condo Holiday Valley, vacation rental in Olean
Updated ski-in/ski-out condo Holiday Valley, vacation rental in Olean
Updated ski-in/ski-out condo Holiday Valley, vacation rental in Olean

Updated ski-in/ski-out condo Holiday Valley

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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Newly renovated ski-in/out condo Holiday Valley, vacation rental in Olean
Newly renovated ski-in/out condo Holiday Valley, vacation rental in Olean
Newly renovated ski-in/out condo Holiday Valley, vacation rental in Olean

Newly renovated ski-in/out condo Holiday Valley

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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5 Bedroom Mansion within minutes to local attractions & shopping, vacation rental in Olean
5 Bedroom Mansion within minutes to local attractions & shopping, vacation rental in Olean
5 Bedroom Mansion within minutes to local attractions & shopping, vacation rental in Olean

5 Bedroom Mansion within minutes to local attractions & shopping

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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MUST SEE!!! - Newly Remodeled 4-bedroom EVL Chalet - Private Setting w/ WiFi, vacation rental in Olean
MUST SEE!!! - Newly Remodeled 4-bedroom EVL Chalet - Private Setting w/ WiFi, vacation rental in Olean
MUST SEE!!! - Newly Remodeled 4-bedroom EVL Chalet - Private Setting w/ WiFi, vacation rental in Olean

MUST SEE!!! - Newly Remodeled 4-bedroom EVL Chalet - Private Setting w/ WiFi

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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New Listing! Cozy Hideaway by St Bonaventure University & Holiday Valley w/ WiFi, vacation rental in Olean
New Listing! Cozy Hideaway by St Bonaventure University & Holiday Valley w/ WiFi, vacation rental in Olean
New Listing! Cozy Hideaway by St Bonaventure University & Holiday Valley w/ WiFi, vacation rental in Olean

New Listing! Cozy Hideaway by St Bonaventure University & Holiday Valley w/ WiFi

Rental Home
5 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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SPRING  is where you need to stay!, vacation rental in Olean
SPRING  is where you need to stay!, vacation rental in Olean
SPRING  is where you need to stay!, vacation rental in Olean

SPRING is where you need to stay!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ski In/ Ski Out, 3 Bedroom & 2 Bath Holiday Valley Condo, vacation rental in Olean
Ski In/ Ski Out, 3 Bedroom & 2 Bath Holiday Valley Condo, vacation rental in Olean
Ski In/ Ski Out, 3 Bedroom & 2 Bath Holiday Valley Condo, vacation rental in Olean

Ski In/ Ski Out, 3 Bedroom & 2 Bath Holiday Valley Condo

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Updated townhome - Walking distance to Holiday Valley Ski Slopes!, vacation rental in Olean
Updated townhome - Walking distance to Holiday Valley Ski Slopes!, vacation rental in Olean
Updated townhome - Walking distance to Holiday Valley Ski Slopes!, vacation rental in Olean

Updated townhome - Walking distance to Holiday Valley Ski Slopes!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Ski In/Out Slopeside Top Notch Condo, All Amenities, vacation rental in Olean
Ski In/Out Slopeside Top Notch Condo, All Amenities, vacation rental in Olean
Ski In/Out Slopeside Top Notch Condo, All Amenities, vacation rental in Olean

Ski In/Out Slopeside Top Notch Condo, All Amenities

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Studio Condo with Murphy bed in Ellicottville walking distance to town, vacation rental in Olean
Beautiful Studio Condo with Murphy bed in Ellicottville walking distance to town, vacation rental in Olean
Beautiful Studio Condo with Murphy bed in Ellicottville walking distance to town, vacation rental in Olean

Beautiful Studio Condo with Murphy bed in Ellicottville walking distance to town

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Great Spot on the Lake!, vacation rental in Olean
Great Spot on the Lake!, vacation rental in Olean
Great Spot on the Lake!, vacation rental in Olean

Great Spot on the Lake!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Special Ski Getaway 8 mins to Ski Resorts Holiday Valley & Holimont Skiing, vacation rental in Olean
Special Ski Getaway 8 mins to Ski Resorts Holiday Valley & Holimont Skiing, vacation rental in Olean
Special Ski Getaway 8 mins to Ski Resorts Holiday Valley & Holimont Skiing, vacation rental in Olean

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Walk to the slopes or The Village- Perfect Location, vacation rental in Olean
Walk to the slopes or The Village- Perfect Location, vacation rental in Olean
Walk to the slopes or The Village- Perfect Location, vacation rental in Olean

Walk to the slopes or The Village- Perfect Location

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Great Valley Mtn. House on 30 Acres w/Pond & Grill, vacation rental in Olean
Great Valley Mtn. House on 30 Acres w/Pond & Grill, vacation rental in Olean
Great Valley Mtn. House on 30 Acres w/Pond & Grill, vacation rental in Olean

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Woodland Log Cabin on Private Pond , vacation rental in Olean
Charming Woodland Log Cabin on Private Pond , vacation rental in Olean
Charming Woodland Log Cabin on Private Pond , vacation rental in Olean

Charming Woodland Log Cabin on Private Pond

Cabin
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ski-in/Ski-out 2 bed, 1 bath condo Holiday Valley, vacation rental in Olean
Ski-in/Ski-out 2 bed, 1 bath condo Holiday Valley, vacation rental in Olean
Ski-in/Ski-out 2 bed, 1 bath condo Holiday Valley, vacation rental in Olean

Ski-in/Ski-out 2 bed, 1 bath condo Holiday Valley

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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NEW! Ski-In Ski-Out Condo at Holiday Valley Resort, vacation rental in Olean
NEW! Ski-In Ski-Out Condo at Holiday Valley Resort, vacation rental in Olean
NEW! Ski-In Ski-Out Condo at Holiday Valley Resort, vacation rental in Olean

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

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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1920s Cuba Lake Cottage with 4 bedrooms and one bathroom, large yard, and dock., vacation rental in Olean
1920s Cuba Lake Cottage with 4 bedrooms and one bathroom, large yard, and dock., vacation rental in Olean
1920s Cuba Lake Cottage with 4 bedrooms and one bathroom, large yard, and dock., vacation rental in Olean

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

Rental Home
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Home on a Hill, vacation rental in Olean
Home on a Hill, vacation rental in Olean
Home on a Hill, vacation rental in Olean

Home on a Hill

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Ski-in/Ski-out 2 Bed, 2 Bath condo Holiday Valley, vacation rental in Olean
Ski-in/Ski-out 2 Bed, 2 Bath condo Holiday Valley, vacation rental in Olean
Ski-in/Ski-out 2 Bed, 2 Bath condo Holiday Valley, vacation rental in Olean

Ski-in/Ski-out 2 Bed, 2 Bath condo Holiday Valley

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Tamarack Club Top Floor slopeside condo sleeps 4, vacation rental in Olean
Tamarack Club Top Floor slopeside condo sleeps 4, vacation rental in Olean
Tamarack Club Top Floor slopeside condo sleeps 4, vacation rental in Olean

Tamarack Club Top Floor slopeside condo sleeps 4

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Beautiful 2000 Sq. Ft., Ski Chalet - Seasonal Rental - 4 miles to Holiday Valley, vacation rental in Olean
Beautiful 2000 Sq. Ft., Ski Chalet - Seasonal Rental - 4 miles to Holiday Valley, vacation rental in Olean
Beautiful 2000 Sq. Ft., Ski Chalet - Seasonal Rental - 4 miles to Holiday Valley, vacation rental in Olean

Beautiful 2000 Sq. Ft., Ski Chalet - Seasonal Rental - 4 miles to Holiday Valley

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Great Valley NY Ski, Bike & Golf Get Away, vacation rental in Olean
Great Valley NY Ski, Bike & Golf Get Away, vacation rental in Olean
Great Valley NY Ski, Bike & Golf Get Away, vacation rental in Olean

Great Valley NY Ski, Bike & Golf Get Away

Rental Home
2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Exceptional Cottage on the North Shore of Cuba Lake, vacation rental in Olean
Exceptional Cottage on the North Shore of Cuba Lake, vacation rental in Olean
Exceptional Cottage on the North Shore of Cuba Lake, vacation rental in Olean

Exceptional Cottage on the North Shore of Cuba Lake

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Timeshare at Holiday Valley Ski/Golf Resort. First Class Amenities, vacation rental in Olean
Timeshare at Holiday Valley Ski/Golf Resort. First Class Amenities, vacation rental in Olean
Timeshare at Holiday Valley Ski/Golf Resort. First Class Amenities, vacation rental in Olean

Timeshare at Holiday Valley Ski/Golf Resort. First Class Amenities

Rental Home
1 bedroom
2 bathrooms
Sleeps 8
Match: Sleeps
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Tamarack Club * Holiday Valley - 1 br condo, vacation rental in Olean
Tamarack Club * Holiday Valley - 1 br condo, vacation rental in Olean
Tamarack Club * Holiday Valley - 1 br condo, vacation rental in Olean

Tamarack Club * Holiday Valley - 1 br condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Alpine Meadows 30, vacation rental in Olean
Alpine Meadows 30, vacation rental in Olean
Alpine Meadows 30, vacation rental in Olean

Alpine Meadows 30

Rental Home
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Myers Chalet, vacation rental in Olean
Myers Chalet, vacation rental in Olean
Myers Chalet, vacation rental in Olean

Myers Chalet

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Smokey Valley Lodge, vacation rental in Olean
Smokey Valley Lodge, vacation rental in Olean
Smokey Valley Lodge, vacation rental in Olean

Smokey Valley Lodge

Rental Home
2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Cozy & Rustic 3 bdr chalet w/ plenty of privacy!, vacation rental in Olean
Cozy & Rustic 3 bdr chalet w/ plenty of privacy!, vacation rental in Olean
Cozy & Rustic 3 bdr chalet w/ plenty of privacy!, vacation rental in Olean

Cozy & Rustic 3 bdr chalet w/ plenty of privacy!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful & rustic 4 bdr Chalet made for memories!, vacation rental in Olean
Beautiful & rustic 4 bdr Chalet made for memories!, vacation rental in Olean
Beautiful & rustic 4 bdr Chalet made for memories!, vacation rental in Olean

Beautiful & rustic 4 bdr Chalet made for memories!

Rental Home
7 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Humphrey Estates, vacation rental in Olean
Humphrey Estates, vacation rental in Olean
Humphrey Estates, vacation rental in Olean

Humphrey Estates

Rental Home
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Wildflower 159, vacation rental in Olean
Wildflower 159, vacation rental in Olean
Wildflower 159, vacation rental in Olean

Wildflower 159

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Ski-in/Ski-out 2 Bed, 2 Bath condo Holiday Valley, vacation rental in Olean
Ski-in/Ski-out 2 Bed, 2 Bath condo Holiday Valley, vacation rental in Olean
Ski-in/Ski-out 2 Bed, 2 Bath condo Holiday Valley, vacation rental in Olean

Ski-in/Ski-out 2 Bed, 2 Bath condo Holiday Valley

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3-bed 2-bath townhouse overlooking Holiday Valley

Rental Home
0 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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