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Fairplay Vacation Rentals

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Fairplay vacation rentals

Interior

1. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (97 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.
$310 nightly
The price is $329
Sep 20 - Sep 21
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Outdoor dining

2. 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
$617 nightly
The price is $672
Sep 22 - Sep 23
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
Interior

3. 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.
$419 nightly
The price is $444
Sep 22 - Sep 23
Total with taxes and fees
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Outdoor dining

4. Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
$292 nightly
The price is $310
Sep 17 - Sep 18
Total with taxes and fees
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Living area

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
$375 nightly
The price is $418
Sep 30 - Oct 1
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Dining

6. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Host let us in a bit early which was nice!"
United States
John
$211 nightly
The price is $235
Sep 21 - Sep 22
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
Interior

7. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
$322 nightly
The price is $359
Sep 22 - Sep 23
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
Private kitchen

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, (16 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
$429 nightly
The price is $455
Sep 27 - Sep 28
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Exterior

9. 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.
$300 nightly
The price is $318
Oct 2 - Oct 3
Total with taxes and fees
Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D
Exterior

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (85 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
$99 nightly
The price is $110
Oct 5 - Oct 6
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

11. 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.
$442 nightly
The price is $492
Sep 17 - Sep 18
Total with taxes and fees
Glamping Clear Spring Maryland 3-Cabin Campground
Living area

12. BEST LOCATION: Historic Shepherdstown Getaway

BEST LOCATION: Historic Shepherdstown Getaway
Shepherdstown
10.0 out of 10, Exceptional, (111 reviews)
"Wonderful host, great location, everything was a expected"
United States
Dave D.
$384 nightly
The price is $431
Sep 28 - Sep 29
Total with taxes and fees
BEST LOCATION: Historic Shepherdstown Getaway
Exterior detail

13. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
10.0 out of 10, Exceptional, (4 reviews)
"This place was amazing! Every little detail was thought of, and makes for just an incredible, delightful stay. Has all the amenities of what you’d expect in a home, yet has the unique appeal of a fantastic little treehouse!!"
United States
Whiskey Dent G.
$201 nightly
The price is $202
Sep 17 - Sep 18
Total with taxes and fees
Bin There Treehouse - A Grain Bin treehouse!
Terrace/patio

14. Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81

Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Hedgesville
9.0 out of 10, Wonderful, (7 reviews)
"Nice clean property. It was spacious and comfortable. "
United States
Diane G.
$99 nightly
The price is $110
Sep 22 - Sep 23
Total with taxes and fees
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Living area

15. 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, (28 reviews)
"We loved staying here. Beautiful views, great communication with Tammie, and very clean. Definitely will stay again!"
United States
Haley H.
$163 nightly
The price is $182
Sep 17 - Sep 18
Total with taxes and fees
Galloping Getaway on the rolling hills of GemStone Stable
Living area

16. 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
$334 nightly
The price is $372
Oct 1 - Oct 2
Total with taxes and fees
Peregrine's Perch - Cabin Overlooking the River!
Room

17. 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, (24 reviews)
"Everything was excellent except climbing up the hill to get to the villas but besides that it was excellent just gotta bring all wheel drive vehicle next time I go"
United States
Glenn
$548 nightly
The price is $592
Oct 7 - Oct 8
Total with taxes and fees
Mirror Villas - Modern Retreat with private hot tubs and mountain view
Room

18. Schilling House

Schilling House
3.0 star property
Bolivar
$321 nightly
The price is $343
Sep 17 - Sep 18
Total with taxes and fees
Schilling House
Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (155 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.
$335 nightly
The price is $355
Sep 27 - Sep 28
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
Private kitchen

20. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
"Cute little cabin. Perfect for our 1 night stay for a concert in the area. Im just sad we left the kids at home cause they would have loved it too!"
United States
Laura K.
$231 nightly
The price is $244
Sep 17 - Sep 18
Total with taxes and fees
Cozy Downtown Cabin - Family Friendly
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

10/10 Excellent
"Great bed and pillows. Great shower. Breakfast was solid. All you can ask for."
Gary 1-night trip
Posted 16 hours ago
Tru By Hilton Martinsburg

Find out more about Fairplay

Everything you need to know about Fairplay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Fairplay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fairplay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Fairplay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fairplay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Fairplay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $110 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Fairplay rentals

At Expedia, we put the best Fairplay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Fairplay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fairplay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fairplay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

A peaceful, forest retreat with stunning views near historic Harpers Ferry.: This vacation home rental near Fairplay offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

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.