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Compare 156 Vacation Homes in Fairplay with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (117)
"We were looking for a quiet getaway location from the Black Friday and Small Business Saturday crowds, but also a location that was close to several small towns near the area...and this property checked all boxes! Everywhere you go within 20-30 minutes is a delight for the history, art, music collector, foodie, entertainment, wine, distillery, brewery, or shopping fanatic...a delightful home and one we hope to visit again!"
The price is AED 661
AED 1,281 total
includes taxes & fees
30 Dec - 31 Dec
Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming 3-Bedroom Home in historic Harpers Ferry: No Pet or Cleaning Fees!

10.0 out of 10, Exceptional, (12)
"Harper’s Ferry is amazing and the property is in the heart of it. Walk to the historical sites or Trail store. Park and ride is less than 5 mins to catch train to DC. Home has a modernized restoration with beautiful aesthetics inside. Large deck with smokeless firepit. Back yard is gated for pups. Many thoughtful amenities. Professionally clean. Nice owners. 10/10"
Charming 3-Bedroom Home in historic Harpers Ferry: No Pet or Cleaning Fees!

Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

7.4 out of 10, Good, (3)
"Nice place that had all the necessary space and amenities for short weekend in Hagerstown. "
The price is AED 360
AED 744 total
includes taxes & fees
31 Dec - 1 January 2025
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (88)
"Great year round location. Owners are nearby if issues occur. HIGHLY RECOMMENDED. "
The price is AED 533
AED 809 total
includes taxes & fees
26 Dec - 27 Dec
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (110)
"This property could not have been more quaint and peaceful. My husband, two dogs and I enjoyed the long weekend, walking the trails and taking in the history of Harper’s Ferry. I would highly recommend this property to anyone looking for a quiet getaway. The location could not be better for seeing the town on foot. The property was clean and so neatly appointed. Breathtaking views! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (110)
"The house was amazing, great views and a great layout that allowed for us to hang as a group or have some privacy. Very convenient to everything we wanted to do; Harper’s Ferry, Ziplining (or rafting based on time of year), and the Brewery that we went to on the last night felt like it was almost walking distance. Definitely recommend and would stay again in a heartbeat. "
Walk to Potomac River and downtown Harpers Ferry

Woods Song - Natures Promise

9.8 out of 10, Exceptional, (32)
"This location was a nice place to stay. Definitely quiet and off the beaten track. We generally stay closer in to Berkeley Springs, but decided this time to go further out of town. The place was very clean and the hot tub was very well maintained. The appliances, as expected, were dated but worked fine. The only potential downside was that there were two other properties right behind this one. In the spring or summer with the trees in full foliage it would be very private. In the late fall a...
Woods Song - Natures Promise

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

10.0 out of 10, Exceptional, (26)
"Beautiful house, wonderful kitchen and dining room. TVs everywhere. Game room. And of course the heated indoor pool. Spent Thanksgiving there. Saw deer outside each morning."
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

A 3-bedroom house just a 20-minute walk from historic Harpers Ferry.

10.0 out of 10, Exceptional, (1)
"Raisa's place was quaint and more than adequate. It was neat and had many interesting plants throughout the house. The backyard was great to have (especially being pet friendly). Access to Harper's Ferry was close by and very convenient. Recommend!"
A 3-bedroom house just a 20-minute walk from historic Harpers Ferry.

Nice and modern decor, 4BR 3BA, remodeled

10.0 out of 10, Exceptional, (15)
"The location was perfect. I was able to visit several of my family members all who were only 5-10 minutes away. The layout was perfect there was more than enough for everyone to be comfortable. My grandchildren only complaint was that there wasn't a pool on the property or a gas stove 😁. They said breakfast took long to get done. We will definitely be year around occupants. We all enjoyed our stay . "
Nice and modern decor, 4BR 3BA, remodeled

Lake House w/ Pool and King Bed, Fishing - Dogs OK

9.4 out of 10, Exceptional, (20)
"The water quality was my only complaint. It was extra hard."
Lake House w/ Pool and King Bed, Fishing - Dogs OK

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

9.6 out of 10, Exceptional, (172)
"We explored Harper’s Ferry and Antietam Battlefield over a beautiful fall weekend. Neither of us are history buffs and didn’t pay much attention to it in school so we learned quite a bit at the National Parks. The home was a perfect theme and location for our weekend. It was interesting to see how the people of the time lived but with modern amenities. We are both tall ladies, (5’11”) so we had to watch our heads. Stairs are steep and tight. "
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

9.8 out of 10, Exceptional, (119)
"Two sisters, a brother and spouses met up in this delightful house in Harpers Ferry. It was spacious and well equipped. There were interesting books and pictures in the house and in all, had a spacious but cozy atmosphere. It waa a nice walk into this quaint, historic town.."
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Spacious Riverview Escape: Just Half Mile to Harpers Ferry National Park Center

10.0 out of 10, Exceptional, (13)
"Everything was as listed! The kids were entertained with all the toys! The view and location were wonderful! Only suggestion we would have if a baby gate for those beautiful stairs. "
Spacious Riverview Escape: Just Half Mile to Harpers Ferry National Park Center

Queen Anne Gem in Historic Harpers Ferry!

9.8 out of 10, Exceptional, (19)
"Gorgeous house, nicely decorated and well located. The owners were easy to reach but also provided lots of great information through their website and guest handbook. Hope to rent from them again. "
Queen Anne Gem in Historic Harpers Ferry!

Pool, Hot Tub, and Fun for all!

10.0 out of 10, Exceptional, (15)
"The house was clean, well maintained and looked just like the pictures. The area was fantastic with tons of options for food and entertainment. Austin was a wonderful host and it was so easy to communicate with him. 100% recommend this location!"
The price is AED 951
AED 1,770 total
includes taxes & fees
24 Dec - 25 Dec
Pool, Hot Tub, and Fun for all!

Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!

9.0 out of 10, Wonderful, (17)
"Beautiful property. Very unique layout that we loved since we don’t love the open concept homes. There are lots of steps. Enter through the back door, with a gorgeous outdoor space, into the kitchen/dining area. Three ways to go 1. Off to one side is the screened in porch. 2. the other - a spacious laundry area that leads to a half bath on one side with a toilet and sinks, and a half bath on other side with a jetted tub and a stand up shower. You can go down the stairs to the large makeup area,...
Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!

Peaceful Home w/ Patio < 2 Mi to Nat'l Park!

10.0 out of 10, Exceptional, (17)
"Everything was perfect, and comfortable. Owners really care about their visitors. Home was walk in perfect for a family long weekend. Happened to be Thurmont's annual colorfest festival, and home pefectly located, nestled away yet close enough for easy walking. Highly recommend. "
Peaceful Home w/ Patio < 2 Mi to Nat'l Park!

ENTIRE DUPLEX!! Views of Shenandoah Mountains and River Wineries and Breweries!

10.0 out of 10, Exceptional, (72)
"Great location, beautiful view, cozy house"
ENTIRE DUPLEX!! Views of Shenandoah Mountains and River Wineries and Breweries!

Charmingly renovated historic Canal House on C&O along Potomac close to Antietam

10.0 out of 10, Exceptional, (74)
"The Canal House is a wonderful home! The house itself is meticulously kept with its history intact while offering a modern kitchen and air conditioning. The grounds are filled with beautiful flowers and a small garden pond. The location was perfect to enjoy biking on the C&O towpath, plus a short drive to Antietam battlefield, tubing, rafting and hiking."
Charmingly renovated historic Canal House on C&O along Potomac close to Antietam
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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Other property types in Fairplay

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (48)
"Excellent little cabin right on the river and close to DT Sheperdstown which is a great town."
The price is AED 162
AED 403 total
includes taxes & fees
30 Dec - 31 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities

10.0 out of 10, Exceptional, (45)
"House was very comfortable for our family. The kids loved the flexibility of the sleeping arrangements. "
Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities

Waterfront Cabin overlooking the Potomac River W/ Hot Tub

9.8 out of 10, Exceptional, (48)
"Super pleased with everything. Enjoyed our stay so. Very much. Would love to come back sometime. "
The price is AED 496
AED 993 total
includes taxes & fees
20 Jan - 21 January 2025
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
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.