Default HTG hotel image

Fairplay Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Fairplay holiday rentals

A room with large windows, wooden floors, and a ceiling fan.

1. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (101 reviews)
"The cabin was clean, spacious, and"
United States
Daniel
The price is AU$505
includes taxes & fees
28 Oct - 29 Oct
Antietam Creek - Quiet 2 Bedroom Cabin
A wooden cabin with a patio area, outdoor seating, and a fire pit.

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, (19 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is AU$465
includes taxes & fees
9 Nov - 10 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

3. 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
Large Family Home: 5 Mi to Dtwn Hagerstown!
A residential area with houses, roads, and green fields.

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

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
The price is AU$442
includes taxes & fees
2 Nov - 3 Nov
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

5. 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 AU$664
includes taxes & fees
28 Oct - 29 Oct
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A wooden deck with a grill, outdoor seating, and a bottle of wine.

6. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
Sharpsburg
10.0 out of 10, Exceptional, (54 reviews)
"The house was in a great location with the winery and battlefield nearby, and the house was very nice and comfortable."
United States
Nancy D.
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

7. 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 AU$644
includes taxes & fees
5 Nov - 6 Nov
Large Family Home: 5 Mi to Dtwn Hagerstown!
A living room with a dining table, chairs, a sofa, and a television.

8. 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 AU$317
includes taxes & fees
28 Oct - 29 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 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 AU$155
includes taxes & fees
8 Nov - 9 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
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)
"The house was as great! Plenty of space for 5 adults. Conveniently located to the areas we wanted to visit. Very quiet location"
United States
Melisa T.
The price is AU$620
includes taxes & fees
12 Nov - 13 Nov
Antietam Look Out - Incredible Sunset Views!
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

11. 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, (77 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 AU$539
includes taxes & fees
3 Nov - 4 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

12. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (55 reviews)
"Nice little place. Hosts were very responsive."
United States
Miki M.
The price is AU$402
includes taxes & fees
12 Nov - 13 Nov
Charming Cabin in the Woods with River Access
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

13. 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, (22 reviews)
"Our stay was so enjoyable!"
United States
Kimberly C.
The price is AU$631
includes taxes & fees
3 Nov - 4 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

14. 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 AU$503
includes taxes & fees
4 Nov - 5 Nov
Peregrine's Perch - Cabin Overlooking the River!
A patio with outdoor furniture, a pool, and a barbecue grill.

15. 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, (9 reviews)
"Property was clean and as described. It was close to our event for the weekend. Only suggestion would be paper towels in the kitchen."
United States
Renee H.
The price is AU$158
includes taxes & fees
28 Oct - 29 Oct
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
A playground with swings, a slide, and a fire pit area with chairs.

16. 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 AU$689
includes taxes & fees
28 Oct - 29 Oct
Glamping Clear Spring Maryland 3-Cabin Campground
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, (117 reviews)
"Beautiful property! Owner is very quick to communicate and did a fantastic job making it a very relaxing place to stay!"
United States
Cindy B.
The price is AU$329
includes taxes & fees
30 Oct - 31 Oct
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A room with a central island, a ceiling fan, a window with blinds, and a wall-mounted shelf.

18. 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 AU$232
includes taxes & fees
30 Oct - 31 Oct
Bring Your Own Boat - Meticulously restored house on the Potomac River
A log cabin interior with a wooden bench, a leather sofa, a coffee table, and a bookshelf.

19. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is AU$372
includes taxes & fees
2 Nov - 3 Nov
Cozy Downtown Cabin - Family Friendly
A spacious living room with a large window, a wooden coffee table, and a sofa.

20. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AU$438
includes taxes & fees
9 Nov - 10 Nov
Schilling House
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Fairplay Hotel Reviews

Tru By Hilton Hagerstown

Tru By Hilton Hagerstown

10/10 Excellent
"Very clean with shopping close by"
Sunday 1-night trip
Posted 3 hours ago
Tru By Hilton Hagerstown

Find out more about Fairplay

Everything you need to know about Fairplay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fairplay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Fairplay holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fairplay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fairplay holiday rentals we have selected for you start as low as AU$329 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Fairplay rentals

At Expedia, we put the best Fairplay holiday 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 holiday.

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 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.