Vacation rentals in Fairplay

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Top-rated vacation rentals in Fairplay

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guest suite in Shepherdstown

4.96 out of 5 average rating, 563 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Jun 27 – Jul 4

R1,761 ZAR per night
Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 247 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Amazing place to unwind, de-stress & get away. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting.

Mar 19 – 26

R2,147 ZAR per night
Guest favorite

Cottage in Sharpsburg

4.95 out of 5 average rating, 151 reviews

Lock Keepers Cottage on C&O Canal/Potomac River

Located just steps away from Dam #4 on the C&O Canal / Potomac River. (marker 84.6) Perfect for a getaway or romantic weekend. Hike/bike the C&O Canal, bring your kayak/canoe/bikes, fish or swim in the river. Sit on the porch and listen to the rumble of the water falling over the dam. Local lore is this was the home of a canal lock keeper or the gate house keeper. Secluded location away from town. NOT A PARTY HOUSE/owner on site in garage apartment. Inquire if a blocked day is available.

Jun 15 – 22

R3,403 ZAR per night

Popular amenities for Fairplay vacation rentals

Other great vacation rentals in Fairplay

Guest favorite

Apartment in Shepherdstown

4.94 out of 5 average rating, 253 reviews

1 Bedroom Apt in Historic Downtown Shepherdstown

Mar 19 – 26

R2,419 ZAR per night
Guest favorite

Home in Sharpsburg

4.84 out of 5 average rating, 221 reviews

Retreat to Antietam/Sharpsburg

Sep 16 – 23

R2,535 ZAR per night
Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 106 reviews

NEW * The Getaway Cottage at Rocky Marsh Farm

Oct 24 – 31

R4,229 ZAR per night
Guest favorite

Cabin in Boonsboro

4.94 out of 5 average rating, 369 reviews

Little Lodge

May 18 – 25

R4,134 ZAR per night
Guest favorite

Guest suite in Hagerstown

5.0 out of 5 average rating, 11 reviews

Clover Cove

Jun 5 – 12

R1,386 ZAR per night
Guest favorite

Home in Boonsboro

5.0 out of 5 average rating, 11 reviews

Historic Stone Cottage-Convenient Location

Jul 21 – 28

R3,748 ZAR per night
Guest favorite

Home in Hagerstown

4.94 out of 5 average rating, 35 reviews

Cozy & relaxing private apartment

Sep 3 – 10

R1,711 ZAR per night
Guest favorite

Apartment in Hagerstown

5.0 out of 5 average rating, 15 reviews

The Violet Femme Studio

Nov 23 – 30

R1,617 ZAR per night
Guest favorite

Home in Hagerstown

5.0 out of 5 average rating, 7 reviews

Hawks Nest Hagerstown

Aug 7 – 14

R1,811 ZAR per night
Guest favorite

Cabin in Myersville

4.98 out of 5 average rating, 57 reviews

Sleepy Hollow Log Cabin

Oct 16 – 23

R2,677 ZAR per night
Guest favorite

Home in Williamsport

4.89 out of 5 average rating, 9 reviews

The best little house

Sep 10 – 17

R2,491 ZAR per night
Guest favorite

Home in Martinsburg

4.84 out of 5 average rating, 50 reviews

Home Comforts, a separate apt of 1500 sqft.

Oct 8 – 15

R1,230 ZAR per night

Destinations to explore

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  5. Fairplay