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Fairplay Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Fairplay holiday rentals

A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (87 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is HK$325
HK$838 total
includes taxes & fees
25 Oct - 26 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

2. 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 HK$1,174
HK$2,604 total
includes taxes & fees
14 Oct - 15 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A living room with a dining table, chairs, a sofa, and a television.

3. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is HK$942
HK$1,738 total
includes taxes & fees
18 Oct - 19 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
A room with large windows, wooden floors, and a ceiling fan.

4. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (100 reviews)
"We had a lovely get-away! Really enjoyed ourselves."
United States
Erinn
The price is HK$1,570
HK$2,604 total
includes taxes & fees
18 Oct - 19 Oct
Antietam Creek - Quiet 2 Bedroom Cabin
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

5. 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 HK$785
HK$2,778 total
includes taxes & fees
14 Oct - 15 Oct
Antietam Look Out - Incredible Sunset Views!
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

6. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
3.0 star property
Williamsport
10.0 out of 10, Exceptional, (1 review)
"The place was just beautiful "
United States
Derrick
The price is HK$1,467
HK$3,525 total
includes taxes & fees
20 Oct - 21 Oct
Large Family Home: 5 Mi to Dtwn Hagerstown!
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

7. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
9.0 out of 10, Wonderful, (4 reviews)
"My friends and I had a wonderful time here for Labor Day! Quiet and a great location for all sorts of activities."
United States
Nick W.
The price is HK$1,123
HK$2,563 total
includes taxes & fees
22 Oct - 23 Oct
Antietam House Historic Sharpsburg Retreat
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

8. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
Williamsport
8.8 out of 10, Excellent, (21 reviews)
"Property was very nice, plenty of room for our family. We would definitely recommend this house and stay there again."
United States
Charlotte S.
The price is HK$1,122
HK$3,547 total
includes taxes & fees
20 Oct - 21 Oct
Large Family Home: 5 Mi to Dtwn Hagerstown!
A patio with outdoor furniture, a pool, and a barbecue grill.

9. 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, (8 reviews)
"Nice clean property. It was spacious and comfortable. "
United States
Diane G.
The price is HK$586
HK$911 total
includes taxes & fees
14 Oct - 15 Oct
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

10. 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 HK$808
HK$2,860 total
includes taxes & fees
29 Oct - 30 Oct
Peregrine's Perch - Cabin Overlooking the River!
A room with a central island, a ceiling fan, a window with blinds, and a wall-mounted shelf.

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

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"Great little place to stay."
United States
Shannon W.
The price is HK$589
HK$1,265 total
includes taxes & fees
14 Oct - 15 Oct
Bring Your Own Boat - Meticulously restored house on the Potomac River
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

12. 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 HK$1,617
HK$3,578 total
includes taxes & fees
19 Oct - 20 Oct
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.

13. 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, (76 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 HK$1,311
HK$3,633 total
includes taxes & fees
20 Oct - 21 Oct
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A house with a deck, outdoor seating, and a fire pit.

14. 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 HK$3,855
HK$6,871 total
includes taxes & fees
10 Nov - 11 Nov
Exclusive Wooded Chalet w Magnificent River Views
Outdoor dining

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

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
The price is HK$2,129
HK$2,457 total
includes taxes & fees
20 Oct - 21 Oct
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
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, (159 reviews)
"Perfect little house in a great historic location."
United States
Donald K.
The price is HK$1,138
HK$2,462 total
includes taxes & fees
19 Oct - 20 Oct
Charming "Cream of the Crop" Cape ~❤️of Middletown
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

17. 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, (116 reviews)
The price is HK$1,138
HK$2,221 total
includes taxes & fees
26 Oct - 27 Oct
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A house with a well-lit entrance, a small garden, and a gravel driveway.

18. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is HK$671
HK$2,031 total
includes taxes & fees
26 Oct - 27 Oct
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
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, (31 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 HK$981
HK$1,502 total
includes taxes & fees
14 Oct - 15 Oct
Galloping Getaway on the rolling hills of GemStone Stable
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

20. 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, (19 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is HK$2,158
HK$3,569 total
includes taxes & fees
22 Oct - 23 Oct
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
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

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

8/10 Good
"I was expecting a hot tub. The gym's treadmills were pretty solid. Pool was good. The breakfast was lacking compared to other Fairfield Marriots is all. They had waffles, bagels, eggs, bacon, and other various toaster prepped items. I was hoping for some quiche, breakfast burritos, and eggs benedict like the one I frequent in Woburn. Not sure if I'd return for that price."
BRIAN 1-night trip
Posted 3 hours ago
Fairfield Inn & Suites by Marriott Hagerstown

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:

  • View our selection of featured holiday rentals in Fairplay
  • Use the map to find apartments and other holiday homes in the Fairplay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Fairplay while they last

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

Frequently asked questions

Can I find holiday rentals in Fairplay?

Yes, there are holiday rentals close to the most popular sights in Fairplay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Fairplay has to offer?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This holiday home rental outside of Fairplay is located in the mountains, and has a patio, a BBQ 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 wider area, you’ll find Antietam National Battlefield and Hagerstown Premium Outlets.

What are holiday rentals like in Fairplay?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Fairplay. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips.