We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Fairplay Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighborhood
50 rentals in Fairplay.
Sort by:
Tripadvisor Sort
Potomac River Retreat | Shepherdstown, WV | Stunning views | 5 acres | 4 BR, vacation rental in Fairplay

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Rose Cottage Bed and Breakfast, vacation rental in Fairplay

Rose Cottage Bed and Breakfast

2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cottage in Shepherdstown, vacation rental in Fairplay

Cottage in Shepherdstown

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Myersville-Private 9 ac cabin on the creek, yet close to it all., vacation rental in Fairplay

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Paradise View OF THE Shenandoah Mountains Wineries and Breweries!!, vacation rental in Fairplay

Paradise View OF THE Shenandoah Mountains Wineries and Breweries!!

4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Family-friendly, centrally located, quiet, updated, historic home built in 1890., vacation rental in Fairplay

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming 'Cream of the Crop' Cape ~❤️of Middletown, vacation rental in Fairplay

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

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Vintage cabin in the ❤️ of Middletown , MD.  Pet friendly and prime location., vacation rental in Fairplay

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Blue Ridge Beauty, River Excitement, Wineries, Breweries, Casino, vacation rental in Fairplay

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

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Country Home with a view of the Mountains and Whitetail Ski Resort, vacation rental in Fairplay

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

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Fairplay rentals sent straight to your email!
RIVERKEEPER INN, Waterfront Property on the Potomac River, vacation rental in Fairplay

RIVERKEEPER INN, Waterfront Property on the Potomac River

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Sunny And Cozy Little Lodge With A Spectacular View Of The Blue Ridge Mountains, vacation 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
More info
Vrbo.com logo
Check in
Check out
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Hom, vacation 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
More info
Vrbo.com logo
Check in
Check out
Private Secluded Estate on 13 Acres, vacation rental in Fairplay

Private Secluded Estate on 13 Acres

6 bedrooms
8 bathrooms
Sleeps 26
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Lock Keepers Cottage on the Potomac River / C&O Canal, vacation rental in Fairplay

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

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
RIVERKEEPER INN, Waterfront Cottage on the Potomac, vacation rental in Fairplay

RIVERKEEPER INN, Waterfront Cottage on the Potomac

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Renovated Mountain Basement Studio Near Wineries Breweries w/ Laundry & Fire Pit, vacation rental in Fairplay

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

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Historic Booth House at the Harpers Ferry KOA, vacation rental in Fairplay

Historic Booth House at the Harpers Ferry KOA

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful 1815 Stone House, private river area, vacation rental in Fairplay

Beautiful 1815 Stone House, private river area

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Titicaca Room, vacation rental in Fairplay

Titicaca Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Hideaway located on the square., vacation rental in Fairplay

The Hideaway located on the square.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The McCoy House at the Harpers Ferry/Civil War Battlefields KOA, vacation rental in Fairplay

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

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Washington House, vacation rental in Fairplay

Washington House

7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Poplar Place at the foot of South Mountain!, vacation rental in Fairplay

The Poplar Place at the foot of South Mountain!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Stay at LARGE, Historic Home & enjoy 5 star BBQ, vacation rental in Fairplay

Stay at LARGE, Historic Home & enjoy 5 star BBQ

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Shanandoah Room, vacation rental in Fairplay

Shanandoah Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Shallows Room, vacation rental in Fairplay

Shallows Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Country Cottage with Super Location All Private Suite & Breakfast Included, vacation rental in Fairplay

Country Cottage with Super Location All Private Suite & Breakfast Included

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cozytown Cottage/horse property near Whitetail Ski Resort, vacation rental in Fairplay

Cozytown Cottage/horse property near Whitetail Ski Resort

4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Dream House on the Potomac River Canyon South Rim, vacation rental in Fairplay

Dream House on the Potomac River Canyon South Rim

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
beautiful Potomac riverfront, vacation rental in Fairplay

beautiful Potomac riverfront

4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Come see us near historic Harper's Ferry West Virginia, vacation rental in Fairplay

Come see us near historic Harper's Ferry West Virginia

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Jefferson House, vacation rental in Fairplay

Jefferson House

3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Check in
Check out
Payment Protection
Lincoln House, vacation rental in Fairplay

Lincoln House

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Adams House, vacation rental in Fairplay

Adams House

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Roosevelt House, vacation rental in Fairplay

Roosevelt House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Beautiful Mansion In The Country, vacation rental in Fairplay

Beautiful Mansion In The Country

5 bedrooms
6 bathrooms
Sleeps 32
Match: Sleeps
More info
Check in
Check out
Payment Protection
Eisenhower House, vacation rental in Fairplay

Eisenhower House

3 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Payment Protection
Harpers Ferry Apartment w/ Private Pool & Hot Tub!, vacation rental in Fairplay

Harpers Ferry Apartment w/ Private Pool & Hot Tub!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Potomac Room, vacation rental in Fairplay

Potomac Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Compound Historic Nature Preserve, vacation rental in Fairplay

Compound Historic Nature Preserve

1 bedroom
1 bathroom
Sleeps 15
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tranquil Farm House, vacation rental in Fairplay

Tranquil Farm House

2 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - 'Autumn Olive' at Evensong Farm -- collab, vacation rental in Fairplay

Tentrr Signature Site - 'Autumn Olive' at Evensong Farm -- collab

1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - 'Wineberry' at Evensong Farm -- collab, vacation rental in Fairplay

Tentrr Signature Site - 'Wineberry' at Evensong Farm -- collab

1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection
Rock Spring Retreat, vacation rental in Fairplay

Rock Spring Retreat

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - Harpers Ferry - Potomac River View Campsite 2, vacation rental in Fairplay

Tentrr Signature Site - Harpers Ferry - Potomac River View Campsite 2

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - Harpers Ferry - Potomac River View Campsite 1, vacation rental in Fairplay

Tentrr Signature Site - Harpers Ferry - Potomac River View Campsite 1

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
5 story hotel, vacation rental in Fairplay

5 story hotel

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cozy Guest House with Swedish sauna & 5 STAR BBQ Hot tub removed due to C V, vacation 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
More info
Vrbo.com logo
Check in
Check out
Clean, Comfortable and Relaxing Short & Long Term Rentals, vacation rental in Fairplay

Clean, Comfortable and Relaxing Short & Long Term Rentals

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
PreviousNext
1
Frequently Asked Questions about Fairplay