Fairplay Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Fairplay vacation rentals

Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (66)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is ￥6,176
￥16,339 total
includes taxes & fees
Jan 6 - Jan 7, 2026
❤️ Secluded 1940s Romantic Tiny House on the River
Game room
Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
10.0 out of 10, Exceptional, (9)
"Cute little house that my husband and I enjoyed for the weekend. Great location close to Martinsburg. It had everything we needed for our weekend The host communicated well, we had no issues, and we would definitely stay here again. Thank you!"
United States
Jennifer E.
The price is ￥11,698
￥25,143 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Bring Your Own Boat - Meticulously restored house on the Potomac River
Interior
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (110)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is ￥11,743
￥30,206 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Fridge, microwave, coffee/tea maker, electric kettle
Cozy Pine Tree Nest

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11)
"Really nice apartment was just what we wanted for a weekend while here to run the JFK 50 miler"
United States
David S.
The price is ￥12,541
￥26,571 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy Pine Tree Nest
Fridge, microwave, oven, stovetop
Hot Tub, Fire Pit, Grill, Deck w/Resort Amenities

Hot Tub, Fire Pit, Grill, Deck w/Resort Amenities

Hot Tub, Fire Pit, Grill, Deck w/Resort Amenities
The Woods
10.0 out of 10, Exceptional, (2)
"Weston was very welcoming and was prompt to answer any questions leading up to the trip. The home was clean and cozy. Although we didn’t use them due to weather, we enjoyed having the option to use the hot tub and fire pit. "
United States
Jaclyn K.
The price is ￥9,545
￥43,590 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hot Tub, Fire Pit, Grill, Deck w/Resort Amenities
Property grounds
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Sleepy Hollow
9.8 out of 10, Exceptional, (11)
"Had an amazing stay! The VRBO was cozy, comfortable and clean in an amazing area. We loved the amenities, relaxing on the deck, by the fire pit, and in the hot tub were perfect! The host, Emily, was amazing and gave lots of great info about the area and was very responsive. Would love to stay here again!"
United States
Sarah H.
The price is ￥11,673
￥41,994 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Property grounds
Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (19)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
The price is ￥13,897
￥22,171 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Birch Cabin at Hunting Creek Hideaway
Smart TV, fireplace
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Blue Ridge Summit
9.4 out of 10, Exceptional, (11)
"Great spot close to the wedding venue!!"
United States
Alfred T.
The price is ￥10,294
￥27,717 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Fridge, microwave, oven, stovetop
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Harpers Ferry
9.2 out of 10, Wonderful, (30)
"The house was very clean upon arrival. We enjoyed spending time in the hot tub and playing pool on a kid’s pool table. It was close the Harper’s Ferry. We also saw deer very close both days we were there, and we loved this!!"
United States
Kelly
The price is ￥25,991
￥46,658 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Exterior
2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
9.4 out of 10, Exceptional, (3)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is ￥24,866
￥43,515 total
includes taxes & fees
Jan 4 - Jan 5, 2026
2-Bedroom cabin Hot tub Fireplace PS5
TV, fireplace, stereo
The Saloon, cabin retreat.

The Saloon, cabin retreat.

The Saloon, cabin retreat.
2.0 star property
Hedgesville
The price is ￥8,533
￥19,891 total
includes taxes & fees
Jan 15 - Jan 16, 2026
The Saloon, cabin retreat.
Property grounds
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (92)
"The Toll House was clean, had all the amenities advertised, and host had great communication. Very nice to have a fenced yard for my small dog to roam. I recommend this to others! "
United States
Sharon
The price is ￥15,597
￥37,027 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Terrace/patio
Charming "Cream of the Crop" Cape ~❤️of Middletown

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (140)
"Love the place will book again"
United States
WAYNE M.
The price is ￥15,597
￥39,679 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Charming "Cream of the Crop" Cape ~❤️of Middletown
Outdoor spa tub
Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi

Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi

Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi
Sleepy Hollow
9.2 out of 10, Wonderful, (9)
"This cabin did not disappoint it was everything we wanted for a quiet get away."
United States
Gail W.
The price is ￥21,168
￥38,892 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi
Dining
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (65)
"Great stay! We would book again. "
United States
Sam F.
The price is ￥15,597
￥56,942 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Fridge, microwave, oven, stovetop
Loft Apt Just off C&O near Harpers Ferry and AT

Loft Apt Just off C&O near Harpers Ferry and AT

Loft Apt Just off C&O near Harpers Ferry and AT
Brunswick
10.0 out of 10, Exceptional, (16)
"Our Hosts were wonderful and the space was great. It sits right off of the bike trail and across the street from a great bakery and bike shop. We thoroughly enjoyed our stay."
United States
Mark B.
The price is ￥15,285
￥28,602 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Loft Apt Just off C&O near Harpers Ferry and AT
Property grounds
Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
10.0 out of 10, Exceptional, (1)
"Clean, great location, and charming/updated space. Highly recommend! Host was super communicative and helpful!! "
United States
Kaitlin L.
The price is ￥18,716
￥36,372 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Historic Getaway near C&O Canal, hiking and biking
Interior
Modern w/Fire Pit, Deck, Grill & Hot Tub

Modern w/Fire Pit, Deck, Grill & Hot Tub

Modern w/Fire Pit, Deck, Grill & Hot Tub
Sleepy Hollow
9.2 out of 10, Wonderful, (13)
"Great little spot. Location is secluded but there are homes very close by. "
United States
stacey f.
The price is ￥21,168
￥40,977 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Modern w/Fire Pit, Deck, Grill & Hot Tub
Exterior
Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (21)
"Very beautiful place to stay, my family and I enjoyed everything that was offered and very scenic great for pictures and overall a great trip with the family "
United States
Blas G.
The price is ￥15,657
￥56,293 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Peregrine's Perch - Cabin Overlooking the River!
TV, fireplace, books, offices
Hot Tub, Fire Pit, Deck, Grill w Resort Amenities

Hot Tub, Fire Pit, Deck, Grill w Resort Amenities

Hot Tub, Fire Pit, Deck, Grill w Resort Amenities
The Woods
9.0 out of 10, Wonderful, (4)
"Great stay! Peaceful and quiet area! Everything was wonderful!"
United States
Stephen C.
The price is ￥22,974
￥45,156 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hot Tub, Fire Pit, Deck, Grill w Resort Amenities
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Fairplay Hotel Reviews

Hillside Inn & Suite

Hillside Inn & Suite

10/10 Excellent
"Room was clean the check in was very nice"
Sallie 1-night trip
Posted 1 day ago
Hillside Inn & Suite

Find out more about Fairplay

Search for holiday rentals in Fairplay on Expedia! You can easily find your home rentals, villas, holiday apartments in Fairplay using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Fairplay?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Fairplay, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Fairplay?

Hot tub, Campfire ring and great location!: This vacation home near Fairplay is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

What can I see and do in Fairplay?

Explore the area and family-friendly sights such as For the Kids, By George Children's Museum, or get out into nature at a spot like Crystal Grottoes Caverns. In the larger area, you’ll find Antietam National Battlefield and Hagerstown Premium Outlets.

What are vacation rentals like in Fairplay?

Vacation rentals are privately owned properties you can book for a couple days or more in Fairplay. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.