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Fairplay Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Fairplay.
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, vacation rental in Fairplay
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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Rose Cottage Bed and Breakfast, vacation rental in Fairplay
Rose Cottage Bed and Breakfast, vacation rental in Fairplay
Rose Cottage Bed and Breakfast, vacation rental in Fairplay

Rose Cottage Bed and Breakfast

Private Room
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Potomac River Getaway - Shepherdstown, WV - Stunning views - 5 acres - 4 BR, vacation rental in Fairplay
Potomac River Getaway - Shepherdstown, WV - Stunning views - 5 acres - 4 BR, vacation rental in Fairplay
Potomac River Getaway - Shepherdstown, WV - Stunning views - 5 acres - 4 BR, vacation rental in Fairplay

Potomac River Getaway - Shepherdstown, WV - Stunning views - 5 acres - 4 BR

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The following properties within 20 miles of Fairplay match all your filters:
Cottage in Shepherdstown, vacation rental in Fairplay
Cottage in Shepherdstown, vacation rental in Fairplay
Cottage in Shepherdstown, vacation rental in Fairplay

Cottage in Shepherdstown

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charmingly renovated historic Canal House on C&O along Potomac close to Antietam, vacation rental in Fairplay
Charmingly renovated historic Canal House on C&O along Potomac close to Antietam, vacation rental in Fairplay
Charmingly renovated historic Canal House on C&O along Potomac close to Antietam, vacation rental in Fairplay

Charmingly renovated historic Canal House on C&O along Potomac close to Antietam

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Modern Two-Story Charmer in Historic Downtown Shepherdstown, vacation rental in Fairplay
Modern Two-Story Charmer in Historic Downtown Shepherdstown, vacation rental in Fairplay
Modern Two-Story Charmer in Historic Downtown Shepherdstown, vacation rental in Fairplay

Modern Two-Story Charmer in Historic Downtown Shepherdstown

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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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, vacation rental in Fairplay
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

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Lock Keepers Cottage on C&O Canal/Potomac River, vacation rental in Fairplay
Lock Keepers Cottage on C&O Canal/Potomac River, vacation rental in Fairplay
Lock Keepers Cottage on C&O Canal/Potomac River, vacation rental in Fairplay

Lock Keepers Cottage on C&O Canal/Potomac River

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Antietam Creek - Quiet 2 Bedroom Cabin, vacation rental in Fairplay
Antietam Creek - Quiet 2 Bedroom Cabin, vacation rental in Fairplay
Antietam Creek - Quiet 2 Bedroom Cabin, vacation rental in Fairplay

Antietam Creek - Quiet 2 Bedroom Cabin

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The C&O Adventure Retreat on Taylor's Landing, vacation rental in Fairplay
The C&O Adventure Retreat on Taylor's Landing, vacation rental in Fairplay
The C&O Adventure Retreat on Taylor's Landing, vacation rental in Fairplay

The C&O Adventure Retreat on Taylor's Landing

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic Hagerstown | Antietam Battle | WhiteTail, vacation rental in Fairplay
Historic Hagerstown | Antietam Battle | WhiteTail, vacation rental in Fairplay
Historic Hagerstown | Antietam Battle | WhiteTail, vacation rental in Fairplay

Historic Hagerstown | Antietam Battle | WhiteTail

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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*Daley's Doll House At Antietam*, vacation rental in Fairplay
*Daley's Doll House At Antietam*, vacation rental in Fairplay
*Daley's Doll House At Antietam*, vacation rental in Fairplay

*Daley's Doll House At Antietam*

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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❤️ Secluded 1940s Romantic Tiny House on the River, vacation rental in Fairplay
❤️ Secluded 1940s Romantic Tiny House on the River, vacation rental in Fairplay
❤️ Secluded 1940s Romantic Tiny House on the River, vacation rental in Fairplay

❤️ Secluded 1940s Romantic Tiny House on the River

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Luxury Cabin Nestled In The Beautiful Blue Ridge Mountains, vacation rental in Fairplay
Luxury Cabin Nestled In The Beautiful Blue Ridge Mountains, vacation rental in Fairplay
Luxury Cabin Nestled In The Beautiful Blue Ridge Mountains, vacation rental in Fairplay

Luxury Cabin Nestled In The Beautiful Blue Ridge Mountains

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Tentrr Signature Site - Evensong Farm - Autumn Olive - Coleman Outfitted Site, vacation rental in Fairplay
Tentrr Signature Site - Evensong Farm - Autumn Olive - Coleman Outfitted Site, vacation rental in Fairplay
Tentrr Signature Site - Evensong Farm - Autumn Olive - Coleman Outfitted Site, vacation rental in Fairplay

Tentrr Signature Site - Evensong Farm - Autumn Olive - Coleman Outfitted Site

Rental Home
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
More info
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The Getaway Cottage at Rocky Marsh Farm, vacation rental in Fairplay
The Getaway Cottage at Rocky Marsh Farm, vacation rental in Fairplay
The Getaway Cottage at Rocky Marsh Farm, vacation rental in Fairplay

The Getaway Cottage at Rocky Marsh Farm

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Dream House on the Potomac River Canyon South Rim, vacation rental in Fairplay
Dream House on the Potomac River Canyon South Rim, vacation rental in Fairplay
Dream House on the Potomac River Canyon South Rim, vacation rental in Fairplay

Dream House on the Potomac River Canyon South Rim

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Downtown Modern 2BR step from dining and shopping, vacation rental in Fairplay
Downtown Modern 2BR step from dining and shopping, vacation rental in Fairplay
Downtown Modern 2BR step from dining and shopping, vacation rental in Fairplay

Downtown Modern 2BR step from dining and shopping

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Historic Townhome in Downtown Shepherdstown!, vacation rental in Fairplay
Historic Townhome in Downtown Shepherdstown!, vacation rental in Fairplay
Historic Townhome in Downtown Shepherdstown!, vacation rental in Fairplay

Historic Townhome in Downtown Shepherdstown!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Cozy Cottage, vacation rental in Fairplay
Cozy Cottage, vacation rental in Fairplay
Cozy Cottage, vacation rental in Fairplay

Cozy Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath, vacation rental in Fairplay
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath, vacation rental in Fairplay
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath, vacation rental in Fairplay

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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*In The Heart Of Antietam*, vacation rental in Fairplay
*In The Heart Of Antietam*, vacation rental in Fairplay
*In The Heart Of Antietam*, vacation rental in Fairplay

*In The Heart Of Antietam*

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Tentrr Signature Site - Evensong Farm - Autumn Olive - Coleman Outfitted Site, vacation rental in Fairplay
Tentrr Signature Site - Evensong Farm - Autumn Olive - Coleman Outfitted Site, vacation rental in Fairplay
Tentrr Signature Site - Evensong Farm - Autumn Olive - Coleman Outfitted Site, vacation rental in Fairplay

Tentrr Signature Site - Evensong Farm - Autumn Olive - Coleman Outfitted Site

Rental Home
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
More info
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Tentrr Signature Site - "Wineberry" at Evensong Farm - Coleman Outfitted Site, vacation rental in Fairplay
Tentrr Signature Site - "Wineberry" at Evensong Farm - Coleman Outfitted Site, vacation rental in Fairplay
Tentrr Signature Site - "Wineberry" at Evensong Farm - Coleman Outfitted Site, vacation rental in Fairplay

Tentrr Signature Site - "Wineberry" at Evensong Farm - Coleman Outfitted Site

Rental Home
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
More info
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5 story hotel, vacation rental in Fairplay
5 story hotel, vacation rental in Fairplay
5 story hotel, vacation rental in Fairplay

5 story hotel

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Tentrr Signature Site - "Wineberry" at Evensong Farm - Coleman Outfitted Site, vacation rental in Fairplay
Tentrr Signature Site - "Wineberry" at Evensong Farm - Coleman Outfitted Site, vacation rental in Fairplay
Tentrr Signature Site - "Wineberry" at Evensong Farm - Coleman Outfitted Site, vacation rental in Fairplay

Tentrr Signature Site - "Wineberry" at Evensong Farm - Coleman Outfitted Site

Rental Home
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
More info
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Gorgeous Riverfront Retreat: swimming, canoeing, riding, biking, vacation rental in Fairplay
Gorgeous Riverfront Retreat: swimming, canoeing, riding, biking, vacation rental in Fairplay
Gorgeous Riverfront Retreat: swimming, canoeing, riding, biking, vacation rental in Fairplay

Gorgeous Riverfront Retreat: swimming, canoeing, riding, biking

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sunny Streams - Mountaintop Cabin with Incredible Sunset Views!, vacation rental in Fairplay
Sunny Streams - Mountaintop Cabin with Incredible Sunset Views!, vacation rental in Fairplay
Sunny Streams - Mountaintop Cabin with Incredible Sunset Views!, vacation rental in Fairplay

Sunny Streams - Mountaintop Cabin with Incredible Sunset Views!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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5 story hotel with luxury comfort, located in the heart of Hagerstown, MD, vacation rental in Fairplay
5 story hotel with luxury comfort, located in the heart of Hagerstown, MD, vacation rental in Fairplay
5 story hotel with luxury comfort, located in the heart of Hagerstown, MD, vacation rental in Fairplay

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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2 Connecting Suites at a  Hotel, vacation rental in Fairplay
2 Connecting Suites at a  Hotel, vacation rental in Fairplay
2 Connecting Suites at a  Hotel, vacation rental in Fairplay

2 Connecting Suites at a Hotel

Rental Home
2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Amazing Home Stays Near Fairgrounds, vacation rental in Fairplay
Amazing Home Stays Near Fairgrounds, vacation rental in Fairplay
Amazing Home Stays Near Fairgrounds, vacation rental in Fairplay

Amazing Home Stays Near Fairgrounds

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Modern chic spacious apartment - One minute walk downtown!!, vacation rental in Fairplay
Modern chic spacious apartment - One minute walk downtown!!, vacation rental in Fairplay
Modern chic spacious apartment - One minute walk downtown!!, vacation rental in Fairplay

Modern chic spacious apartment - One minute walk downtown!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!, vacation rental in Fairplay
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!, vacation rental in Fairplay
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!, vacation rental in Fairplay

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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‘Cool Hollow House’ Historic Hagerstown Retreat!, vacation rental in Fairplay
‘Cool Hollow House’ Historic Hagerstown Retreat!, vacation rental in Fairplay
‘Cool Hollow House’ Historic Hagerstown Retreat!, vacation rental in Fairplay

‘Cool Hollow House’ Historic Hagerstown Retreat!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Lovely Townhome Near Museum & Historic Sites!, vacation rental in Fairplay
Lovely Townhome Near Museum & Historic Sites!, vacation rental in Fairplay
Lovely Townhome Near Museum & Historic Sites!, vacation rental in Fairplay

Lovely Townhome Near Museum & Historic Sites!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Stunning custom Shepherdstown waterfront retreat, vacation rental in Fairplay
Stunning custom Shepherdstown waterfront retreat, vacation rental in Fairplay
Stunning custom Shepherdstown waterfront retreat, vacation rental in Fairplay

Stunning custom Shepherdstown waterfront retreat

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Nice and modern decor, 4BR 3BA, remodeled, vacation rental in Fairplay
Nice and modern decor, 4BR 3BA, remodeled, vacation rental in Fairplay
Nice and modern decor, 4BR 3BA, remodeled, vacation rental in Fairplay

Nice and modern decor, 4BR 3BA, remodeled

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Boonsboro Studio w/ Wood-Burning Fire Pit!, vacation rental in Fairplay
Boonsboro Studio w/ Wood-Burning Fire Pit!, vacation rental in Fairplay
Boonsboro Studio w/ Wood-Burning Fire Pit!, vacation rental in Fairplay

Boonsboro Studio w/ Wood-Burning Fire Pit!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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1879 Updated Home on Frederick Street, vacation rental in Fairplay
1879 Updated Home on Frederick Street, vacation rental in Fairplay
1879 Updated Home on Frederick Street, vacation rental in Fairplay

1879 Updated Home on Frederick Street

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Charming Historic Heights Neighborhood Apartment, vacation rental in Fairplay
Charming Historic Heights Neighborhood Apartment, vacation rental in Fairplay
Charming Historic Heights Neighborhood Apartment, vacation rental in Fairplay

Charming Historic Heights Neighborhood Apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Beautiful river in front of home, vacation rental in Fairplay
Beautiful river in front of home, vacation rental in Fairplay
Beautiful river in front of home, vacation rental in Fairplay

Beautiful river in front of home

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Historic & Cozy ~ Near Antietam Battle & WhiteTail, vacation rental in Fairplay
Historic & Cozy ~ Near Antietam Battle & WhiteTail, vacation rental in Fairplay
Historic & Cozy ~ Near Antietam Battle & WhiteTail, vacation rental in Fairplay

Historic & Cozy ~ Near Antietam Battle & WhiteTail

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Fell like home one hour away from Washington DC private parking and patio, vacation rental in Fairplay
Fell like home one hour away from Washington DC private parking and patio, vacation rental in Fairplay
Fell like home one hour away from Washington DC private parking and patio, vacation rental in Fairplay

Fell like home one hour away from Washington DC private parking and patio

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Modern-Chic Cozy w/KING; Hospital, HCC, I-70, vacation rental in Fairplay
Modern-Chic Cozy w/KING; Hospital, HCC, I-70, vacation rental in Fairplay
Modern-Chic Cozy w/KING; Hospital, HCC, I-70, vacation rental in Fairplay

Modern-Chic Cozy w/KING; Hospital, HCC, I-70

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Comfy Room near Hagerstown & Martinsburg, vacation rental in Fairplay
Comfy Room near Hagerstown & Martinsburg, vacation rental in Fairplay
Comfy Room near Hagerstown & Martinsburg, vacation rental in Fairplay

Comfy Room near Hagerstown & Martinsburg

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Grammy's Place: A Vintage Grandma's Haven!, vacation rental in Fairplay
Grammy's Place: A Vintage Grandma's Haven!, vacation rental in Fairplay
Grammy's Place: A Vintage Grandma's Haven!, vacation rental in Fairplay

Grammy's Place: A Vintage Grandma's Haven!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Comfy 2 bedroom apartment with Shared entrancea and Kitchen., vacation rental in Fairplay
Comfy 2 bedroom apartment with Shared entrancea and Kitchen., vacation rental in Fairplay
Comfy 2 bedroom apartment with Shared entrancea and Kitchen., vacation rental in Fairplay

Comfy 2 bedroom apartment with Shared entrancea and Kitchen.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Welcome to the Shepherds Rest, vacation rental in Fairplay
Welcome to the Shepherds Rest, vacation rental in Fairplay
Welcome to the Shepherds Rest, vacation rental in Fairplay

Welcome to the Shepherds Rest

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic Stone House close local activites and National Parks, vacation rental in Fairplay
Historic Stone House close local activites and National Parks, vacation rental in Fairplay
Historic Stone House close local activites and National Parks, vacation rental in Fairplay

Historic Stone House close local activites and National Parks

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Cozy Attic!
With adjustable office space and ergonomic king size bed., vacation rental in Fairplay
Cozy Attic!
With adjustable office space and ergonomic king size bed., vacation rental in Fairplay
Cozy Attic!
With adjustable office space and ergonomic king size bed., vacation rental in Fairplay

Cozy Attic! With adjustable office space and ergonomic king size bed.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Showing results 1-50 of 50
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