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Greencastle Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
47 rentals in Greencastle.
Beautifully Restored Stone Farmhouse, holiday rental in Greencastle
Beautifully Restored Stone Farmhouse, holiday rental in Greencastle
Beautifully Restored Stone Farmhouse, holiday rental in Greencastle

Beautifully Restored Stone Farmhouse

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Traveling to the area for work, we offer discounted rates for long term rentals., holiday rental in Greencastle
Traveling to the area for work, we offer discounted rates for long term rentals., holiday rental in Greencastle
Traveling to the area for work, we offer discounted rates for long term rentals., holiday rental in Greencastle

Traveling to the area for work, we offer discounted rates for long term rentals.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozytown Cottage near Whitetail Ski Resort and Hagerstown Maryland., holiday rental in Greencastle
Cozytown Cottage near Whitetail Ski Resort and Hagerstown Maryland., holiday rental in Greencastle
Cozytown Cottage near Whitetail Ski Resort and Hagerstown Maryland., holiday rental in Greencastle

Cozytown Cottage near Whitetail Ski Resort and Hagerstown Maryland.

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The following properties within 20 miles of Greencastle match all your filters:
Antietam Toll House~ an historic waterfront cabin, holiday rental in Greencastle
Antietam Toll House~ an historic waterfront cabin, holiday rental in Greencastle
Antietam Toll House~ an historic waterfront cabin, holiday rental in Greencastle

Antietam Toll House~ an historic waterfront cabin

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historic & Cozy ~ Near Antietam Battle & WhiteTail, holiday rental in Greencastle
Historic & Cozy ~ Near Antietam Battle & WhiteTail, holiday rental in Greencastle
Historic & Cozy ~ Near Antietam Battle & WhiteTail, holiday rental in Greencastle

Historic & Cozy ~ Near Antietam Battle & WhiteTail

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Boho Penthouse on Main, holiday rental in Greencastle
The Boho Penthouse on Main, holiday rental in Greencastle
The Boho Penthouse on Main, holiday rental in Greencastle

The Boho Penthouse on Main

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Fort Chambers Flat on Main, holiday rental in Greencastle
Fort Chambers Flat on Main, holiday rental in Greencastle
Fort Chambers Flat on Main, holiday rental in Greencastle

Fort Chambers Flat on Main

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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gorgeous.., holiday rental in Greencastle
gorgeous.., holiday rental in Greencastle
gorgeous.., holiday rental in Greencastle

gorgeous..

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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202 - Buchanan Room - James Buchanan Hotel, holiday rental in Greencastle
202 - Buchanan Room - James Buchanan Hotel, holiday rental in Greencastle
202 - Buchanan Room - James Buchanan Hotel, holiday rental in Greencastle

202 - Buchanan Room - James Buchanan Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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206A - Elizabeth's Room - James Buchanan Hotel, holiday rental in Greencastle
206A - Elizabeth's Room - James Buchanan Hotel, holiday rental in Greencastle
206A - Elizabeth's Room - James Buchanan Hotel, holiday rental in Greencastle

206A - Elizabeth's Room - James Buchanan Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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207 - Harriet's Room - James Buchanan Hotel, holiday rental in Greencastle
207 - Harriet's Room - James Buchanan Hotel, holiday rental in Greencastle
207 - Harriet's Room - James Buchanan Hotel, holiday rental in Greencastle

207 - Harriet's Room - James Buchanan Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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208 - Ms. Hetty's Room - James Buchanan Hotel, holiday rental in Greencastle
208 - Ms. Hetty's Room - James Buchanan Hotel, holiday rental in Greencastle
208 - Ms. Hetty's Room - James Buchanan Hotel, holiday rental in Greencastle

208 - Ms. Hetty's Room - James Buchanan Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Cutest Loft on Main St!, holiday rental in Greencastle
The Cutest Loft on Main St!, holiday rental in Greencastle
The Cutest Loft on Main St!, holiday rental in Greencastle

The Cutest Loft on Main St!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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302 - The McLaughlin Suite - James Buchanan Hotel, holiday rental in Greencastle
302 - The McLaughlin Suite - James Buchanan Hotel, holiday rental in Greencastle
302 - The McLaughlin Suite - James Buchanan Hotel, holiday rental in Greencastle

302 - The McLaughlin Suite - James Buchanan Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2 Bedroom Spacious Stay near Historic Hagerstown, holiday rental in Greencastle
2 Bedroom Spacious Stay near Historic Hagerstown, holiday rental in Greencastle
2 Bedroom Spacious Stay near Historic Hagerstown, holiday rental in Greencastle

2 Bedroom Spacious Stay near Historic Hagerstown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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206A & 206B - Elizabeth's Suite - James Buchanan Hotel, holiday rental in Greencastle
206A & 206B - Elizabeth's Suite - James Buchanan Hotel, holiday rental in Greencastle
206A & 206B - Elizabeth's Suite - James Buchanan Hotel, holiday rental in Greencastle

206A & 206B - Elizabeth's Suite - James Buchanan Hotel

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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201A - Après-Ski Room - James Buchanan Hotel, holiday rental in Greencastle
201A - Après-Ski Room - James Buchanan Hotel, holiday rental in Greencastle
201A - Après-Ski Room - James Buchanan Hotel, holiday rental in Greencastle

201A - Après-Ski Room - James Buchanan Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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201A & 201B - Après-Ski Suite - James Buchanan Hotel, holiday rental in Greencastle
201A & 201B - Après-Ski Suite - James Buchanan Hotel, holiday rental in Greencastle
201A & 201B - Après-Ski Suite - James Buchanan Hotel, holiday rental in Greencastle

201A & 201B - Après-Ski Suite - James Buchanan Hotel

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Creekside Cottage, A beautiful Pennsylvania retreat., holiday rental in Greencastle
Creekside Cottage, A beautiful Pennsylvania retreat., holiday rental in Greencastle
Creekside Cottage, A beautiful Pennsylvania retreat., holiday rental in Greencastle

Creekside Cottage, A beautiful Pennsylvania retreat.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cedar Hill Cottage, the Perfect Getaway in Chambersburg PA, holiday rental in Greencastle
Cedar Hill Cottage, the Perfect Getaway in Chambersburg PA, holiday rental in Greencastle
Cedar Hill Cottage, the Perfect Getaway in Chambersburg PA, holiday rental in Greencastle

Cedar Hill Cottage, the Perfect Getaway in Chambersburg PA

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Central, Beautiful Apartment in Downtown Chambersburg, holiday rental in Greencastle
Central, Beautiful Apartment in Downtown Chambersburg, holiday rental in Greencastle
Central, Beautiful Apartment in Downtown Chambersburg, holiday rental in Greencastle

Central, Beautiful Apartment in Downtown Chambersburg

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Mercersburg Cottage, 7 Mi to Whitetail Resort, holiday rental in Greencastle
Mercersburg Cottage, 7 Mi to Whitetail Resort, holiday rental in Greencastle
Mercersburg Cottage, 7 Mi to Whitetail Resort, holiday rental in Greencastle

Mercersburg Cottage, 7 Mi to Whitetail Resort

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Rancher in Mont Alto, holiday rental in Greencastle
Rancher in Mont Alto, holiday rental in Greencastle
Rancher in Mont Alto, holiday rental in Greencastle

Rancher in Mont Alto

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Spacious creekside townhome in the heart of Chambersburg!, holiday rental in Greencastle
Spacious creekside townhome in the heart of Chambersburg!, holiday rental in Greencastle
Spacious creekside townhome in the heart of Chambersburg!, holiday rental in Greencastle

Spacious creekside townhome in the heart of Chambersburg!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Industrial Modern Living, holiday rental in Greencastle
Industrial Modern Living, holiday rental in Greencastle
Industrial Modern Living, holiday rental in Greencastle

Industrial Modern Living

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Warm Spring Farmhouse, Old Charm with Modern Updates in Historic Chambersburg, holiday rental in Greencastle
Warm Spring Farmhouse, Old Charm with Modern Updates in Historic Chambersburg, holiday rental in Greencastle
Warm Spring Farmhouse, Old Charm with Modern Updates in Historic Chambersburg, holiday rental in Greencastle

Warm Spring Farmhouse, Old Charm with Modern Updates in Historic Chambersburg

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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1879 Updated Home on Frederick Street, holiday rental in Greencastle
1879 Updated Home on Frederick Street, holiday rental in Greencastle
1879 Updated Home on Frederick Street, holiday rental in Greencastle

1879 Updated Home on Frederick Street

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lily Pad - Tiny Home at Mane & Co. / Free Parking, holiday rental in Greencastle
Lily Pad - Tiny Home at Mane & Co. / Free Parking, holiday rental in Greencastle
Lily Pad - Tiny Home at Mane & Co. / Free Parking, holiday rental in Greencastle

Lily Pad - Tiny Home at Mane & Co. / Free Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Corner on Welty, Townhouse in Waynesboro, holiday rental in Greencastle
The Corner on Welty, Townhouse in Waynesboro, holiday rental in Greencastle
The Corner on Welty, Townhouse in Waynesboro, holiday rental in Greencastle

The Corner on Welty, Townhouse in Waynesboro

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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5 mins to the Outlets Beautiful Mango Mania Palace, holiday rental in Greencastle
5 mins to the Outlets Beautiful Mango Mania Palace, holiday rental in Greencastle
5 mins to the Outlets Beautiful Mango Mania Palace, holiday rental in Greencastle

5 mins to the Outlets Beautiful Mango Mania Palace

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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20 Minutes from Skiing, Snow tubing - SF Home with Jetted Bathtub, holiday rental in Greencastle
20 Minutes from Skiing, Snow tubing - SF Home with Jetted Bathtub, holiday rental in Greencastle
20 Minutes from Skiing, Snow tubing - SF Home with Jetted Bathtub, holiday rental in Greencastle

20 Minutes from Skiing, Snow tubing - SF Home with Jetted Bathtub

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Mane & Co - No. 6, holiday rental in Greencastle
The Mane & Co - No. 6, holiday rental in Greencastle
The Mane & Co - No. 6, holiday rental in Greencastle

The Mane & Co - No. 6

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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205 - James's Room - James Buchanan Hotel, holiday rental in Greencastle
205 - James's Room - James Buchanan Hotel, holiday rental in Greencastle
205 - James's Room - James Buchanan Hotel, holiday rental in Greencastle

205 - James's Room - James Buchanan Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2 Storie, Hot Tub, Open Area, holiday rental in Greencastle
2 Storie, Hot Tub, Open Area, holiday rental in Greencastle
2 Storie, Hot Tub, Open Area, holiday rental in Greencastle

2 Storie, Hot Tub, Open Area

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Charming Historic Heights Neighborhood Apartment, holiday rental in Greencastle
Charming Historic Heights Neighborhood Apartment, holiday rental in Greencastle
Charming Historic Heights Neighborhood Apartment, holiday rental in Greencastle

Charming Historic Heights Neighborhood Apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Amazing Home Stays Near Fairgrounds, holiday rental in Greencastle
Amazing Home Stays Near Fairgrounds, holiday rental in Greencastle
Amazing Home Stays Near Fairgrounds, holiday rental in Greencastle

Amazing Home Stays Near Fairgrounds

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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The Drifter - Tiny home at Mane & Co., holiday rental in Greencastle
The Drifter - Tiny home at Mane & Co., holiday rental in Greencastle
The Drifter - Tiny home at Mane & Co., holiday rental in Greencastle

The Drifter - Tiny home at Mane & Co.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Beautiful Mansion in the Country & Wedding Venue, holiday rental in Greencastle
Beautiful Mansion in the Country & Wedding Venue, holiday rental in Greencastle
Beautiful Mansion in the Country & Wedding Venue, holiday rental in Greencastle

Beautiful Mansion in the Country & Wedding Venue

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 32
Match: Sleeps
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Mountain view, rural and cozy., holiday rental in Greencastle
Mountain view, rural and cozy., holiday rental in Greencastle
Mountain view, rural and cozy., holiday rental in Greencastle

Mountain view, rural and cozy.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5 story hotel with luxury comfort, located in the heart of Hagerstown, MD, holiday rental in Greencastle
5 story hotel with luxury comfort, located in the heart of Hagerstown, MD, holiday rental in Greencastle
5 story hotel with luxury comfort, located in the heart of Hagerstown, MD, holiday rental in Greencastle

5 story hotel with luxury comfort, located in the heart of Hagerstown, MD

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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SPRINGHOUSE  1803 - UNIQUE HISTORIC HOME, holiday rental in Greencastle
SPRINGHOUSE  1803 - UNIQUE HISTORIC HOME, holiday rental in Greencastle
SPRINGHOUSE  1803 - UNIQUE HISTORIC HOME, holiday rental in Greencastle

SPRINGHOUSE 1803 - UNIQUE HISTORIC HOME

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous Spacious w/KING; W-Mart, Eats, shopping!, holiday rental in Greencastle
Gorgeous Spacious w/KING; W-Mart, Eats, shopping!, holiday rental in Greencastle
Gorgeous Spacious w/KING; W-Mart, Eats, shopping!, holiday rental in Greencastle

Gorgeous Spacious w/KING; W-Mart, Eats, shopping!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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301 - The Mercer Suite - James Buchanan Hotel, holiday rental in Greencastle
301 - The Mercer Suite - James Buchanan Hotel, holiday rental in Greencastle
301 - The Mercer Suite - James Buchanan Hotel, holiday rental in Greencastle

301 - The Mercer Suite - James Buchanan Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Charming 2-bedroom house with peaceful front porch and game room in Hagerstown, holiday rental in Greencastle
Charming 2-bedroom house with peaceful front porch and game room in Hagerstown, holiday rental in Greencastle
Charming 2-bedroom house with peaceful front porch and game room in Hagerstown, holiday rental in Greencastle

Charming 2-bedroom house with peaceful front porch and game room in Hagerstown

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Biophilic Loft,  curated and styled by REmix Design, holiday rental in Greencastle
Biophilic Loft,  curated and styled by REmix Design, holiday rental in Greencastle
Biophilic Loft,  curated and styled by REmix Design, holiday rental in Greencastle

Biophilic Loft, curated and styled by REmix Design

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Historic Hagerstown Haven: Walk to Parks, Downtown, holiday rental in Greencastle
Historic Hagerstown Haven: Walk to Parks, Downtown, holiday rental in Greencastle
Historic Hagerstown Haven: Walk to Parks, Downtown, holiday rental in Greencastle

Historic Hagerstown Haven: Walk to Parks, Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Spacious Getaway: 7 Mi to Whitetail Slopes!, holiday rental in Greencastle
Spacious Getaway: 7 Mi to Whitetail Slopes!, holiday rental in Greencastle
Spacious Getaway: 7 Mi to Whitetail Slopes!, holiday rental in Greencastle

Spacious Getaway: 7 Mi to Whitetail Slopes!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-47 of 47
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