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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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, (88 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is £79
includes taxes & fees
18 Nov - 19 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
A rustic building with a sign reading 'The Robin's Nest' and a front door.

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)
"Cute place with a lot of character. Host was very responsive. We enjoyed our sray."
United States
Dawn V.
The price is £240
includes taxes & fees
15 Nov - 16 Nov
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, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is £159
includes taxes & fees
15 Nov - 16 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

4. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (46 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 £291
includes taxes & fees
18 Nov - 19 Nov
Antietam Look Out - Incredible Sunset Views!
A room with large windows, wooden floors, and a ceiling fan.

5. 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 £260
includes taxes & fees
15 Nov - 16 Nov
Antietam Creek - Quiet 2 Bedroom Cabin
A patio with outdoor furniture, a pool, and a barbecue grill.

6. 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)
"Nice clean property. It was spacious and comfortable. "
United States
Diane G.
The price is £79
includes taxes & fees
18 Nov - 19 Nov
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

7. 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, (78 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 £432
includes taxes & fees
15 Nov - 16 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

8. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
Shepherdstown
9.4 out of 10, Exceptional, (6 reviews)
"Very nice place, the lay out is perfect for multiple adults, we stayed for 10 night for work and it was perfect, we will be back for another long stay soon. "
United States
Brandon K.
The price is £275
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

9. 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 £285
includes taxes & fees
19 Nov - 20 Nov
Peregrine's Perch - Cabin Overlooking the River!
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

10. 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)
"I was surprised to see how dilapidated the decking around the house was. I was concerned we might trip or fall through. The location was ideal for bicycling and fishing . The backyard was beautiful with the most prettiest flowers and trees."
United States
Susie R.
The price is £313
includes taxes & fees
30 Nov - 1 Dec
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

11. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (57 reviews)
"Great property to stay at and would definitely stay there again! Very peaceful!"
United States
Christopher
The price is £195
includes taxes & fees
24 Nov - 25 Nov
Charming Cabin in the Woods with River Access
A room with a central island, a ceiling fan, a window with blinds, and a wall-mounted shelf.

12. 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 £116
includes taxes & fees
15 Nov - 16 Nov
Bring Your Own Boat - Meticulously restored house on the Potomac River
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

13. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is £266
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

14. 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, (118 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 £162
includes taxes & fees
15 Nov - 16 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A lakeside setting with wooden chairs and a picnic table, surrounded by lush greenery and trees.

15. 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, (110 reviews)
"This was our 4th stay and enjoyed every one!"
United States
Anonymous traveller
The price is £139
includes taxes & fees
20 Nov - 21 Nov
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

16. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
9.8 out of 10, Exceptional, (6 reviews)
"Such a neat place! Very peaceful setting."
United States
Abby G.
The price is £158
includes taxes & fees
15 Nov - 16 Nov
Bin There Treehouse - A Grain Bin treehouse!
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is £200
includes taxes & fees
16 Nov - 17 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

18. 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 £320
includes taxes & fees
18 Nov - 19 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
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, (33 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 £140
includes taxes & fees
13 Nov - 14 Nov
Galloping Getaway on the rolling hills of GemStone Stable
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

20. Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
10.0 out of 10, Exceptional, (71 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
The price is £130
includes taxes & fees
15 Nov - 16 Nov
Cozy Getaway near Harper`s Ferry, C&O & Potomac
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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Find holiday rentals that suit your style

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Top Fairplay Hotel Reviews

An outdoor patio with a fire pit, seating, and a covered area.
Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown
Hagerstown

8/10 Good

Great stay and lovely swim. Spacious room
United Kingdom
Joanna
Reviewed June 26, 2025
Fairfield Inn & Suites by Marriott 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, apart-hotels, 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 favorite 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 depends 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 £79 per night. Entering your travel dates in the search wizard you might find 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.