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Greencastle Vacation Rentals

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50 rentals in Greencastle.
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Country Home with a view of the Mountains and Whitetail Ski Resort, vacation rental in Greencastle
Country Home with a view of the Mountains and Whitetail Ski Resort, vacation rental in Greencastle
Country Home with a view of the Mountains and Whitetail Ski Resort, vacation rental in Greencastle

Country Home with a view of the Mountains and Whitetail Ski Resort

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Cozytown Cottage/horse property near Whitetail Ski Resort, vacation rental in Greencastle
Cozytown Cottage/horse property near Whitetail Ski Resort, vacation rental in Greencastle
Cozytown Cottage/horse property near Whitetail Ski Resort, vacation rental in Greencastle

Cozytown Cottage/horse property near Whitetail Ski Resort

Rental Home
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Ready to Make Plans?  Close to fall and winter activities!, vacation rental in Greencastle
Ready to Make Plans?  Close to fall and winter activities!, vacation rental in Greencastle
Ready to Make Plans?  Close to fall and winter activities!, vacation rental in Greencastle

Ready to Make Plans? Close to fall and winter activities!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private 1880's 3 bedroom home on 130 acre family cattle farm, vacation rental in Greencastle
Private 1880's 3 bedroom home on 130 acre family cattle farm, vacation rental in Greencastle
Private 1880's 3 bedroom home on 130 acre family cattle farm, vacation rental in Greencastle

Private 1880's 3 bedroom home on 130 acre family cattle farm

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Vacation of a Lifetime - Hike - Bike - Ski - Ride and More!, vacation rental in Greencastle
Vacation of a Lifetime - Hike - Bike - Ski - Ride and More!, vacation rental in Greencastle
Vacation of a Lifetime - Hike - Bike - Ski - Ride and More!, vacation rental in Greencastle

Vacation of a Lifetime - Hike - Bike - Ski - Ride and More!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Cedar Hill Cottage, the Perfect Getaway in Chambersburg PA, vacation rental in Greencastle
Cedar Hill Cottage, the Perfect Getaway in Chambersburg PA, vacation rental in Greencastle
Cedar Hill Cottage, the Perfect Getaway in Chambersburg PA, vacation rental in Greencastle

Cedar Hill Cottage, the Perfect Getaway in Chambersburg PA

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Rustic Cabin in Thurmont, MD, vacation rental in Greencastle
Rustic Cabin in Thurmont, MD, vacation rental in Greencastle
Rustic Cabin in Thurmont, MD, vacation rental in Greencastle

Rustic Cabin in Thurmont, MD

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Private home surrounded by State Game Lands in little Cove, vacation rental in Greencastle
Private home surrounded by State Game Lands in little Cove, vacation rental in Greencastle
Private home surrounded by State Game Lands in little Cove, vacation rental in Greencastle

Private home surrounded by State Game Lands in little Cove

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Near Whitetail, Berkeley Springs, Mercersburg, Hagerstown, Antietam, Frederick, vacation rental in Greencastle
Near Whitetail, Berkeley Springs, Mercersburg, Hagerstown, Antietam, Frederick, vacation rental in Greencastle
Near Whitetail, Berkeley Springs, Mercersburg, Hagerstown, Antietam, Frederick, vacation rental in Greencastle

Near Whitetail, Berkeley Springs, Mercersburg, Hagerstown, Antietam, Frederick

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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SPRINGHOUSE  1803 - UNIQUE HISTORIC HOME, vacation rental in Greencastle
SPRINGHOUSE  1803 - UNIQUE HISTORIC HOME, vacation rental in Greencastle
SPRINGHOUSE  1803 - UNIQUE HISTORIC HOME, vacation rental in Greencastle

SPRINGHOUSE 1803 - UNIQUE HISTORIC HOME

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Ledge at Liberty Mountain, vacation rental in Greencastle
The Ledge at Liberty Mountain, vacation rental in Greencastle
The Ledge at Liberty Mountain, vacation rental in Greencastle

The Ledge at Liberty Mountain

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful, Spacious Historic Victorian Near Ski Liberty, vacation rental in Greencastle
Beautiful, Spacious Historic Victorian Near Ski Liberty, vacation rental in Greencastle
Beautiful, Spacious Historic Victorian Near Ski Liberty, vacation rental in Greencastle

Beautiful, Spacious Historic Victorian Near Ski Liberty

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Cozy streamside cabin, convenient to Ski Liberty and Gettysburg, vacation rental in Greencastle
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg, vacation rental in Greencastle
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg, vacation rental in Greencastle

Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg, vacation rental in Greencastle
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg, vacation rental in Greencastle
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg, vacation rental in Greencastle

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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A Cottage in Woods Near Skiing, Lake, and Historical Sites, vacation rental in Greencastle
A Cottage in Woods Near Skiing, Lake, and Historical Sites, vacation rental in Greencastle
A Cottage in Woods Near Skiing, Lake, and Historical Sites, vacation rental in Greencastle

A Cottage in Woods Near Skiing, Lake, and Historical Sites

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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1 Mile to Whitetail Resort - Mercersberg A Frame!, vacation rental in Greencastle
1 Mile to Whitetail Resort - Mercersberg A Frame!, vacation rental in Greencastle
1 Mile to Whitetail Resort - Mercersberg A Frame!, vacation rental in Greencastle

1 Mile to Whitetail Resort - Mercersberg A Frame!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Beautiful private property in rural environment overlooking Ski Liberty., vacation rental in Greencastle
Beautiful private property in rural environment overlooking Ski Liberty., vacation rental in Greencastle
Beautiful private property in rural environment overlooking Ski Liberty., vacation rental in Greencastle

Beautiful private property in rural environment overlooking Ski Liberty.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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PLEASANT VALLEY ACRES HISTORIC FARMHOUSE, vacation rental in Greencastle
PLEASANT VALLEY ACRES HISTORIC FARMHOUSE, vacation rental in Greencastle
PLEASANT VALLEY ACRES HISTORIC FARMHOUSE, vacation rental in Greencastle

PLEASANT VALLEY ACRES HISTORIC FARMHOUSE

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Rustic Lodge In The Blue Ridge Mountains, 8 Miles South Of Gettysburg, vacation rental in Greencastle
Rustic Lodge In The Blue Ridge Mountains, 8 Miles South Of Gettysburg, vacation rental in Greencastle
Rustic Lodge In The Blue Ridge Mountains, 8 Miles South Of Gettysburg, vacation rental in Greencastle

Rustic Lodge In The Blue Ridge Mountains, 8 Miles South Of Gettysburg

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Spacious Mercersburg Home at Whitetail Resort, vacation rental in Greencastle
Spacious Mercersburg Home at Whitetail Resort, vacation rental in Greencastle
Spacious Mercersburg Home at Whitetail Resort, vacation rental in Greencastle

Spacious Mercersburg Home at Whitetail Resort

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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The Mountains Chalet in Private Rural Environment, vacation rental in Greencastle
The Mountains Chalet in Private Rural Environment, vacation rental in Greencastle
The Mountains Chalet in Private Rural Environment, vacation rental in Greencastle

The Mountains Chalet in Private Rural Environment

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Lincoln House   (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle
The Lincoln House   (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle
The Lincoln House   (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle

The Lincoln House (or for retreats book the whole Caboose Farm compound)

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Mountaintop breezes!--Amazing  view central to Many battlefields, vacation rental in Greencastle
Mountaintop breezes!--Amazing  view central to Many battlefields, vacation rental in Greencastle
Mountaintop breezes!--Amazing  view central to Many battlefields, vacation rental in Greencastle

Mountaintop breezes!--Amazing view central to Many battlefields

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Historic Hagerstown | Antietam Battle | WhiteTail, vacation rental in Greencastle
Historic Hagerstown | Antietam Battle | WhiteTail, vacation rental in Greencastle
Historic Hagerstown | Antietam Battle | WhiteTail, vacation rental in Greencastle

Historic Hagerstown | Antietam Battle | WhiteTail

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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The Jefferson House (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle
The Jefferson House (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle
The Jefferson House (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle

The Jefferson House (or for retreats book the whole Caboose Farm compound)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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The Adams House (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle
The Adams House (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle
The Adams House (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle

The Adams House (or for retreats book the whole Caboose Farm compound)

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Washington House, vacation rental in Greencastle
Washington House, vacation rental in Greencastle
Washington House, vacation rental in Greencastle

Washington House

Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
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The Gatehouse at Loudon Forge, vacation rental in Greencastle
The Gatehouse at Loudon Forge, vacation rental in Greencastle
The Gatehouse at Loudon Forge, vacation rental in Greencastle

The Gatehouse at Loudon Forge

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Rose Cottage Bed and Breakfast, vacation rental in Greencastle
Rose Cottage Bed and Breakfast, vacation rental in Greencastle
Rose Cottage Bed and Breakfast, vacation rental in Greencastle

Rose Cottage Bed and Breakfast

Private Room
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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The Roosevelt House  (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle
The Roosevelt House  (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle
The Roosevelt House  (or for retreats book the whole Caboose Farm compound), vacation rental in Greencastle

The Roosevelt House (or for retreats book the whole Caboose Farm compound)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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A beautiful Pennsylvania retreat., vacation rental in Greencastle
A beautiful Pennsylvania retreat., vacation rental in Greencastle
A beautiful Pennsylvania retreat., vacation rental in Greencastle

A beautiful Pennsylvania retreat.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Hill Top Retreat Cottage With Amazing Views, vacation rental in Greencastle
Hill Top Retreat Cottage With Amazing Views, vacation rental in Greencastle
Hill Top Retreat Cottage With Amazing Views, vacation rental in Greencastle

Hill Top Retreat Cottage With Amazing Views

Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Jefferson House, vacation rental in Greencastle
Jefferson House, vacation rental in Greencastle
Jefferson House, vacation rental in Greencastle

Jefferson House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Lincoln House, vacation rental in Greencastle
Lincoln House, vacation rental in Greencastle
Lincoln House, vacation rental in Greencastle

Lincoln House

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Adams House, vacation rental in Greencastle
Adams House, vacation rental in Greencastle
Adams House, vacation rental in Greencastle

Adams House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Roosevelt House, vacation rental in Greencastle
Roosevelt House, vacation rental in Greencastle
Roosevelt House, vacation rental in Greencastle

Roosevelt House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Mansion In The Country, vacation rental in Greencastle
Beautiful Mansion In The Country, vacation rental in Greencastle
Beautiful Mansion In The Country, vacation rental in Greencastle

Beautiful Mansion In The Country

Rental Home
5 bedrooms
6 bathrooms
Sleeps 32
Match: Sleeps
More info
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Eisenhower House, vacation rental in Greencastle
Eisenhower House, vacation rental in Greencastle
Eisenhower House, vacation rental in Greencastle

Eisenhower House

Rental Home
3 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
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Whitetail Ski & Golf Resort, vacation rental in Greencastle
Whitetail Ski & Golf Resort, vacation rental in Greencastle
Whitetail Ski & Golf Resort, vacation rental in Greencastle

Whitetail Ski & Golf Resort

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Among the Trees, Minutes from Liberty Mtn., vacation rental in Greencastle
Among the Trees, Minutes from Liberty Mtn., vacation rental in Greencastle
Among the Trees, Minutes from Liberty Mtn., vacation rental in Greencastle

Among the Trees, Minutes from Liberty Mtn.

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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RV and Camper Lots/ Cabins and tent lots coming in near future , vacation rental in Greencastle
RV and Camper Lots/ Cabins and tent lots coming in near future , vacation rental in Greencastle
RV and Camper Lots/ Cabins and tent lots coming in near future , vacation rental in Greencastle

RV and Camper Lots/ Cabins and tent lots coming in near future

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Hill Top Retreat Cottage With Amazing Views, vacation rental in Greencastle
Hill Top Retreat Cottage With Amazing Views, vacation rental in Greencastle
Hill Top Retreat Cottage With Amazing Views, vacation rental in Greencastle

Hill Top Retreat Cottage With Amazing Views

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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A Beautiful House in a Retreat Center on Mountain, vacation rental in Greencastle
A Beautiful House in a Retreat Center on Mountain, vacation rental in Greencastle
A Beautiful House in a Retreat Center on Mountain, vacation rental in Greencastle

A Beautiful House in a Retreat Center on Mountain

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Astonishing Airy Mountain Top Retreat, vacation rental in Greencastle
Astonishing Airy Mountain Top Retreat, vacation rental in Greencastle
Astonishing Airy Mountain Top Retreat, vacation rental in Greencastle

Astonishing Airy Mountain Top Retreat

Rental Home
7 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
More info
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Beautiful Mansion in the Country & Wedding Venue, vacation rental in Greencastle
Beautiful Mansion in the Country & Wedding Venue, vacation rental in Greencastle
Beautiful Mansion in the Country & Wedding Venue, vacation rental in Greencastle

Beautiful Mansion in the Country & Wedding Venue

Rental Home
6 bedrooms
6 bathrooms
Sleeps 32
Match: Sleeps
More info
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Deerwood Estates ~ 2 Homes, Sleeps 24, Families, vacation rental in Greencastle
Deerwood Estates ~ 2 Homes, Sleeps 24, Families, vacation rental in Greencastle
Deerwood Estates ~ 2 Homes, Sleeps 24, Families, vacation rental in Greencastle

Deerwood Estates ~ 2 Homes, Sleeps 24, Families

Rental Home
9 bedrooms
4 bathrooms
Sleeps 24
Match: Sleeps
More info
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5 story hotel, vacation rental in Greencastle
5 story hotel, vacation rental in Greencastle
5 story hotel, vacation rental in Greencastle

5 story hotel

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Scenic Mountaintop Villa with Free WiFi & Pool, vacation rental in Greencastle
Scenic Mountaintop Villa with Free WiFi & Pool, vacation rental in Greencastle
Scenic Mountaintop Villa with Free WiFi & Pool, vacation rental in Greencastle

Scenic Mountaintop Villa with Free WiFi & Pool

Rental Home
8 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
More info
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Hagerstown Antietam Battlefield WhiteTail - Two-Bedroom Apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Luxurious Beautiful Mountain Top Retreat, vacation rental in Greencastle
Luxurious Beautiful Mountain Top Retreat, vacation rental in Greencastle
Luxurious Beautiful Mountain Top Retreat, vacation rental in Greencastle

Luxurious Beautiful Mountain Top Retreat

Rental Home
9 bedrooms
5 bathrooms
Sleeps 25
Match: Sleeps
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