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Fairplay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Fairplay vacation rentals

A gravel driveway leading to a house with a brick exterior and a wooden deck.

1. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Boonsboro
9.8 out of 10, Exceptional, (18 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is ￥23,549
￥52,555 total
includes taxes & fees
Oct 1 - Oct 2
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A room with large windows, wooden floors, and a ceiling fan.

2. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (98 reviews)
"We had a great stay! Everything was clean & well organized. The house was well stocked with everything we need. We would definitely stay here again."
United States
Stephen V.
The price is ￥31,474
￥52,212 total
includes taxes & fees
Oct 1 - Oct 2
Antietam Creek - Quiet 2 Bedroom Cabin
A house with a deck, outdoor seating, and a fire pit.

3. Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (20 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is ￥68,676
￥110,134 total
includes taxes & fees
Oct 14 - Oct 15
Exclusive Wooded Chalet w Magnificent River Views
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

4. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Sharpsburg
8.2 out of 10, Very good, (66 reviews)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is ￥32,434
￥71,747 total
includes taxes & fees
Oct 15 - Oct 16
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

5. 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, (75 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
The price is ￥24,550
￥70,519 total
includes taxes & fees
Oct 20 - Oct 21
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A living room with a dining table, chairs, a sofa, and a television.

6. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"We loved staying here, and walking into town to.explore. The kitchen was well stocked, and the tub was.perfect for soaking after a long day hiking."
United States
Alexandra Z.
The price is ￥25,966
￥43,447 total
includes taxes & fees
Oct 13 - Oct 14
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious living room with a staircase, a sofa, a television, and a large window.

7. BEST LOCATION: Historic Shepherdstown Getaway

BEST LOCATION: Historic Shepherdstown Getaway
Shepherdstown
10.0 out of 10, Exceptional, (112 reviews)
"Wonderful host, great location, everything was a expected"
United States
Dave D.
BEST LOCATION: Historic Shepherdstown Getaway
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

8. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is ￥43,277
￥71,563 total
includes taxes & fees
Oct 7 - Oct 8
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A modern bedroom with a large bed, a view of a forest through floor-to-ceiling windows, and a minimalist design.

9. Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
Mercersburg
10.0 out of 10, Exceptional, (26 reviews)
"Great place to unwind and relax."
United States
Candace
The price is ￥58,368
￥88,400 total
includes taxes & fees
Oct 28 - Oct 29
Mirror Villas - Modern Retreat with private hot tubs and mountain view
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

10. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
The price is ￥18,727
￥59,960 total
includes taxes & fees
Oct 14 - Oct 15
Antietam Look Out - Incredible Sunset Views!
A building with a red brick pathway leading to a white metal fence.

11. Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D

Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D
Hagerstown
10.0 out of 10, Exceptional, (3 reviews)
"Carrie was very responsive and helpful. The location is as advertised. Would stay again for sure."
United States
Mark P.
The price is ￥30,845
￥48,543 total
includes taxes & fees
Oct 30 - Oct 31
Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D
A playground with swings, a slide, and a fire pit area with chairs.

12. Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
9.8 out of 10, Exceptional, (17 reviews)
"Welcoming and spacious for all invitees and we did not even have a chance to explore all the areas that were surrounding as it was a work related trip but will get out there at some later point for a completely relaxing stay for sure"
United States
Image M.
The price is ￥42,026
￥77,441 total
includes taxes & fees
Oct 1 - Oct 2
Glamping Clear Spring Maryland 3-Cabin Campground
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

13. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (86 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is ￥7,225
￥17,598 total
includes taxes & fees
Oct 8 - Oct 9
❤️ Secluded 1940s Romantic Tiny House on the River
A large, curved metal building with a covered entrance and two chairs outside.

14. Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!

Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
Sharpsburg
9.4 out of 10, Exceptional, (6 reviews)
"We enjoyed the views."
United States
Shena M.
Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

15. Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (24 reviews)
"Relaxing, close to all."
United States
Valarie
The price is ￥15,737
￥56,757 total
includes taxes & fees
Oct 1 - Oct 2
Peregrine's Perch - Cabin Overlooking the River!
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (157 reviews)
"Great place to stay. Very clean and beautiful. The Host was very nice too and kept us informed. We will definetly stay there again!"
United States
Adair M.
The price is ￥14,950
￥39,868 total
includes taxes & fees
Oct 4 - Oct 5
Charming "Cream of the Crop" Cape ~❤️of Middletown
A garden with a stone fountain, a wooden deck, and a metal fence.

17. Hillside Hideaway in Lowertown Harpers Ferry

Hillside Hideaway in Lowertown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (23 reviews)
"Perfect location for a visit to Harper’s Ferry "
United States
Evelyn C.
The price is ￥51,932
￥81,694 total
includes taxes & fees
Oct 1 - Oct 2
Hillside Hideaway in Lowertown Harpers Ferry
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

18. Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Harpers Ferry
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is ￥42,525
￥85,089 total
includes taxes & fees
Oct 7 - Oct 8
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
A living room with a sofa, a TV mounted on the wall, and a large sliding glass door leading to a garden.

19. Galloping Getaway on the rolling hills of GemStone Stable

Galloping Getaway on the rolling hills of GemStone Stable
Hagerstown
10.0 out of 10, Exceptional, (30 reviews)
"We loved staying here. Beautiful views, great communication with Tammie, and very clean. Definitely will stay again!"
United States
Haley H.
The price is ￥19,671
￥29,774 total
includes taxes & fees
Oct 1 - Oct 2
Galloping Getaway on the rolling hills of GemStone Stable
A modern kitchen with stainless steel appliances, a dining area with a round table, and a spiral staircase leading to a living area with a sofa and a coffee table.

20. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (33 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
United States
Zachary S.
The price is ￥34,354
￥58,095 total
includes taxes & fees
Oct 4 - Oct 5
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
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

Tru By Hilton Martinsburg

Tru By Hilton Martinsburg

8/10 Good
"The room was comfortable and clean. The free coffee and tea all day was a life saver but the breakfast was lacking a bit for my taste (no big deal there are plenty of places to go). Staff was friendly and helpful and most everything was pretty clean, there was a bus load of people one night so the trash filled up fast by that’s not the hotels fault. Overall 9.5/10 would recommend staying there."
Natasha 4-night trip
Posted 2 days ago
Tru By Hilton Martinsburg

Find out more about Fairplay

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Look no further and take a look at our great range of rental properties in Fairplay!

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?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This vacation home rental near Fairplay is located in the mountains and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Fairplay?

Explore the area and family-friendly sights such as Hagerstown Roundhouse 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.