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Fairplay Holiday Rentals

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50 rentals in Fairplay.
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Potomac River Retreat | Shepherdstown, WV | Stunning views | 5 acres | 4 BR, holiday rental in Fairplay

Potomac River Retreat | Shepherdstown, WV | Stunning views | 5 acres | 4 BR

4 bedrooms
2 bathrooms
Sleeps 8
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Rose Cottage Bed and Breakfast, holiday rental in Fairplay

Rose Cottage Bed and Breakfast

2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Cottage in Shepherdstown, holiday rental in Fairplay

Cottage in Shepherdstown

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Paradise View OF THE Shenandoah Mountains Wineries and Breweries!!, holiday rental in Fairplay

Paradise View OF THE Shenandoah Mountains Wineries and Breweries!!

4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Family-friendly, centrally located, quiet, updated, historic home built in 1890., holiday rental in Fairplay

Family-friendly, centrally located, quiet, updated, historic home built in 1890.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Myersville-Private 9 ac cabin on the creek, yet close to it all., holiday rental in Fairplay

Myersville-Private 9 ac cabin on the creek, yet close to it all.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 'Cream of the Crop' Cape ~❤️of Middletown, holiday rental in Fairplay

Charming 'Cream of the Crop' Cape ~❤️of Middletown

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vintage cabin in the ❤️ of Middletown , MD.  Pet friendly and prime location., holiday rental in Fairplay

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Secluded Estate on 13 Acres, holiday rental in Fairplay

Private Secluded Estate on 13 Acres

6 bedrooms
8 bathrooms
Sleeps 26
Match: Sleeps
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Blue Ridge Beauty, River Excitement, Wineries, Breweries, Casino, holiday rental in Fairplay

Blue Ridge Beauty, River Excitement, Wineries, Breweries, Casino

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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RIVERKEEPER INN, Waterfront Property on the Potomac River, holiday rental in Fairplay

RIVERKEEPER INN, Waterfront Property on the Potomac River

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sunny And Cozy Little Lodge With A Spectacular View Of The Blue Ridge Mountains, holiday rental in Fairplay

Sunny And Cozy Little Lodge With A Spectacular View Of The Blue Ridge Mountains

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Hom, holiday rental in Fairplay

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Hom

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Country Home with a view of the Mountains and Whitetail Ski Resort, holiday rental in Fairplay

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

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Lock Keepers Cottage on the Potomac River / C&O Canal, holiday rental in Fairplay

Lock Keepers Cottage on the Potomac River / C&O Canal

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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RIVERKEEPER INN, Waterfront Cottage on the Potomac, holiday rental in Fairplay

RIVERKEEPER INN, Waterfront Cottage on the Potomac

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated Mountain Basement Studio Near Wineries Breweries w/ Laundry & Fire Pit, holiday rental in Fairplay

Renovated Mountain Basement Studio Near Wineries Breweries w/ Laundry & Fire Pit

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historic Booth House at the Harpers Ferry KOA, holiday rental in Fairplay

Historic Booth House at the Harpers Ferry KOA

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful 1815 Stone House, private river area, holiday rental in Fairplay

Beautiful 1815 Stone House, private river area

1 bedroom
2 bathrooms
Sleeps 4
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Titicaca Room, holiday rental in Fairplay

Titicaca Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Hideaway located on the square., holiday rental in Fairplay

The Hideaway located on the square.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The McCoy House at the Harpers Ferry/Civil War Battlefields KOA, holiday rental in Fairplay

The McCoy House at the Harpers Ferry/Civil War Battlefields KOA

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Washington House, holiday rental in Fairplay

Washington House

7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Harpers Ferry Mountain Retreat - 3 Bedroom Near Wineries w/ Laundry & Fire Pit, holiday rental in Fairplay

Harpers Ferry Mountain Retreat - 3 Bedroom Near Wineries w/ Laundry & Fire Pit

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Shanandoah Room, holiday rental in Fairplay

Shanandoah Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Shallows Room, holiday rental in Fairplay

Shallows Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Country Cottage with Super Location All Private Suite & Breakfast Included, holiday rental in Fairplay

Country Cottage with Super Location All Private Suite & Breakfast Included

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Dream House on the Potomac River Canyon South Rim, holiday rental in Fairplay

Dream House on the Potomac River Canyon South Rim

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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beautiful Potomac riverfront, holiday rental in Fairplay

beautiful Potomac riverfront

4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Come see us near historic Harper's Ferry West Virginia, holiday rental in Fairplay

Come see us near historic Harper's Ferry West Virginia

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stay at LARGE, Historic Home & enjoy 5 star BBQ, holiday rental in Fairplay

Stay at LARGE, Historic Home & enjoy 5 star BBQ

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Jefferson House, holiday rental in Fairplay

Jefferson House

3 bedrooms
2 bathrooms
Sleeps 11
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Lincoln House, holiday rental in Fairplay

Lincoln House

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Adams House, holiday rental in Fairplay

Adams House

4 bedrooms
2 bathrooms
Sleeps 10
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Roosevelt House, holiday rental in Fairplay

Roosevelt House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Mansion In The Country, holiday rental in Fairplay

Beautiful Mansion In The Country

5 bedrooms
6 bathrooms
Sleeps 32
Match: Sleeps
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Eisenhower House, holiday rental in Fairplay

Eisenhower House

3 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Harpers Ferry Apartment w/ Private Pool & Hot Tub!, holiday rental in Fairplay

Harpers Ferry Apartment w/ Private Pool & Hot Tub!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Potomac Room, holiday rental in Fairplay

Potomac Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Compound Historic Nature Preserve, holiday rental in Fairplay

Compound Historic Nature Preserve

1 bedroom
1 bathroom
Sleeps 15
Match: Sleeps
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The Antietam Creek Toll House, holiday rental in Fairplay

The Antietam Creek Toll House

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozytown Cottage/horse property near Whitetail Ski Resort, holiday rental in Fairplay

Cozytown Cottage/horse property near Whitetail Ski Resort

4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A-Frame w/ Mtn Views: 1 Mile to Whitetail Resort!, holiday rental in Fairplay

A-Frame w/ Mtn Views: 1 Mile to Whitetail Resort!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tranquil Farm House, holiday rental in Fairplay

Tranquil Farm House

2 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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The Poplar Place at the foot of South Mountain!, holiday rental in Fairplay

The Poplar Place at the foot of South Mountain!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - 'Autumn Olive' at Evensong Farm, holiday rental in Fairplay

Tentrr Signature Site - 'Autumn Olive' at Evensong Farm

1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - 'Wineberry' at Evensong Farm, holiday rental in Fairplay

Tentrr Signature Site - 'Wineberry' at Evensong Farm

1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
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NEW! 'Slopeside Serenity' Condo w/ On-Site Skiing!, holiday rental in Fairplay

NEW! 'Slopeside Serenity' Condo w/ On-Site Skiing!

2 bedrooms
1 bathroom
Sleeps 13
Match: Sleeps
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Cozy Guest House with Swedish sauna & 5 STAR BBQ Hot tub removed due to C V, holiday rental in Fairplay

Cozy Guest House with Swedish sauna & 5 STAR BBQ Hot tub removed due to C V

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Clean, Comfortable and Relaxing Short & Long Term Rentals, holiday rental in Fairplay

Clean, Comfortable and Relaxing Short & Long Term Rentals

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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