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Fairplay Vacation Rentals

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Check prices for these dates

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

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)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is ￥7,347
￥16,521 total
includes taxes & fees
Nov 29 - Nov 30
❤️ Secluded 1940s Romantic Tiny House on the River
A backyard with a patio, outdoor seating, a fire pit, and a small shed.

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 ￥23,899
￥50,967 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥21,082
￥35,989 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥15,971
￥73,377 total
includes taxes & fees
Nov 18 - Nov 19
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 ￥35,935
￥55,190 total
includes taxes & fees
Nov 15 - Nov 16
Antietam Creek - Quiet 2 Bedroom Cabin
A spacious living room with wooden walls and large windows, a fireplace, and a view of the outdoors.

6. 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 ￥15,971
￥73,828 total
includes taxes & fees
Nov 17 - Nov 18
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A nighttime forest path lit by string lights.

7. 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, (55 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.
The price is ￥21,721
￥54,327 total
includes taxes & fees
Nov 15 - Nov 16
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
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 ￥13,416
￥58,243 total
includes taxes & fees
Nov 19 - Nov 20
Walk to Stores: Home in Historic Shepherdstown!
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, (9 reviews)
"Nice clean property. It was spacious and comfortable. "
United States
Diane G.
The price is ￥10,924
￥16,054 total
includes taxes & fees
Nov 18 - Nov 19
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
A fire pit with three lounge chairs in a forest setting.

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 ￥15,971
￥70,105 total
includes taxes & fees
Nov 18 - Nov 19
Peregrine's Perch - Cabin Overlooking the River!
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

11. 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 ￥12,777
￥32,843 total
includes taxes & fees
Nov 15 - Nov 16
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
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.
The price is ￥11,978
￥24,391 total
includes taxes & fees
Nov 15 - Nov 16
Bring Your Own Boat - Meticulously restored house on the Potomac River
DECK -stairway to the deck from outside. And additional way to sneak out.

13. 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 ￥30,760
￥67,650 total
includes taxes & fees
Nov 30 - Dec 1
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A hallway with a door leading to a dining area.

14. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is ￥19,325
￥56,726 total
includes taxes & fees
Nov 19 - Nov 20
Walk to Stores: Home in Historic Shepherdstown!
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

15. 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 ￥23,557
￥41,154 total
includes taxes & fees
Nov 24 - Nov 25
Charming Cabin in the Woods with River Access
A single-story house with a red front door, a small porch, and a mailbox.

16. 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 ￥14,374
￥40,122 total
includes taxes & fees
Nov 15 - Nov 16
Charming "Cream of the Crop" Cape ~❤️of Middletown
Two wooden Adirondack chairs by a calm river, surrounded by trees and a small rustic building in the background.

17. 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 ￥16,610
￥29,332 total
includes taxes & fees
Nov 20 - Nov 21
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
A treehouse with wooden platforms and a metal structure, surrounded by tall trees.

18. 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 ￥23,142
￥30,715 total
includes taxes & fees
Nov 15 - Nov 16
Bin There Treehouse - A Grain Bin treehouse!
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

19. 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 ￥15,811
￥26,917 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Getaway near Harper`s Ferry, C&O & Potomac
A backyard with a grill, outdoor seating, a fenced area, and a grassy field.

20. 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 ￥19,964
￥28,205 total
includes taxes & fees
Nov 15 - Nov 16
Galloping Getaway on the rolling hills of GemStone Stable
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

The Plaza Inn & Suites

The Plaza Inn & Suites

8/10 Good
"Very helpful employee and room was clean"
Rodney 1-night trip
Posted 2 hours ago
The Plaza Inn & Suites

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:

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

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.