Fairplay Vacation Rentals

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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 vacation rentals

A hammock hanging from a tree by a lake.

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)
"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 AED 169
AED 380 total
includes taxes & fees
29 Nov - 30 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 AED 550
AED 1,172 total
includes taxes & fees
15 Nov - 16 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A spacious attic bedroom with a sloped ceiling, a large window, and a view of the outdoors.

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 AED 441
AED 774 total
includes taxes & fees
15 Nov - 16 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance
An outdoor covered patio with wicker furniture and string lights, overlooking a forested area.

4. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (46 reviews)
"Beautiful house. Spent most of our time at the house sitting on the deck."
United States
Betty M.
The price is AED 367
AED 1,688 total
includes taxes & fees
18 Nov - 19 Nov
Antietam Look Out - Incredible Sunset Views!
A wooden deck leading to a cabin surrounded by dense forest.

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 AED 826
AED 1,269 total
includes taxes & fees
16 Nov - 17 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 AED 258
AED 377 total
includes taxes & fees
18 Nov - 19 Nov
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
A spacious living room with wooden walls and large windows, a fireplace, and 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 AED 599
AED 2,121 total
includes taxes & fees
15 Nov - 16 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A hallway with a door leading to a dining area.

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 AED 309
AED 1,339 total
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!
A fire pit with three lounge chairs in a forest setting.

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
Peregrine's Perch - Cabin Overlooking the River!
DECK -stairway to the deck from outside. And additional way to sneak out.

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 AED 698
AED 1,545 total
includes taxes & fees
16 Nov - 17 Nov
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 AED 542
AED 946 total
includes taxes & fees
24 Nov - 25 Nov
Charming Cabin in the Woods with River Access
A grassy area with a small pavilion, a lake, and trees.

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.
Bring Your Own Boat - Meticulously restored house on the Potomac River
A hallway with a door leading to a dining area.

13. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is AED 444
AED 1,305 total
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 AED 312
AED 779 total
includes taxes & fees
15 Nov - 16 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Two wooden Adirondack chairs by a calm river, surrounded by trees and a small rustic building in the background.

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 traveler
The price is AED 382
AED 675 total
includes taxes & fees
20 Nov - 21 Nov
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
A treehouse with wooden platforms and a metal structure, surrounded by tall trees.

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 AED 591
AED 769 total
includes taxes & fees
15 Nov - 16 Nov
Bin There Treehouse - A Grain Bin treehouse!
A single-story house with a red front door, a small porch, and a mailbox.

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 AED 367
AED 966 total
includes taxes & fees
15 Nov - 16 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 AED 1,010
AED 1,585 total
includes taxes & fees
19 Nov - 20 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A backyard with a grill, outdoor seating, a fenced area, and a grassy field.

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 AED 459
AED 672 total
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 AED 364
AED 619 total
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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Top Fairplay Hotel Reviews

A Fairfield by Marriott Inn & Suites building with a modern architectural design, featuring a prominent entrance and multiple floors.
Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown
Hagerstown

10/10 Excellent

Free breakfast was good. Staff friendly
United States
Christine
Reviewed November 10, 2026
Fairfield Inn & Suites by Marriott Hagerstown

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.