Default HTG hotel image

Fairplay Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Fairplay vacation 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)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
$88 nightly
The price is $98
Nov 15 - Nov 16
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
A wooden cabin with a patio area, outdoor seating, and a fire pit.

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)
"Extremely cute and a wonderful place to relax."
United States
A D.
$306 nightly
The price is $316
Nov 5 - Nov 6
Total with taxes and fees
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, (26 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
$189 nightly
The price is $211
Nov 8 - Nov 9
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

4. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
3.0 star property
Williamsport
10.0 out of 10, Exceptional, (1 review)
"The place was just beautiful "
United States
Derrick
$401 nightly
The price is $449
Nov 5 - Nov 6
Total with taxes and fees
Large Family Home: 5 Mi to Dtwn Hagerstown!
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
$323 nightly
The price is $342
Nov 5 - Nov 6
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

6. 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.
$352 nightly
The price is $393
Nov 18 - Nov 19
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
A wooden deck with a grill, outdoor seating, and a bottle of wine.

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, (54 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.
$264 nightly
The price is $295
Nov 5 - Nov 6
Total with taxes and fees
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

8. 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, (77 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$418 nightly
The price is $467
Nov 19 - Nov 20
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

9. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
Williamsport
8.8 out of 10, Excellent, (21 reviews)
"Property was very nice, plenty of room for our family. We would definitely recommend this house and stay there again."
United States
Charlotte S.
$388 nightly
The price is $433
Nov 5 - Nov 6
Total with taxes and fees
Large Family Home: 5 Mi to Dtwn Hagerstown!
A patio with outdoor furniture, a pool, and a barbecue grill.

10. 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.
$91 nightly
The price is $102
Nov 11 - Nov 12
Total with taxes and fees
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

11. 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.
$330 nightly
The price is $350
Dec 5 - Dec 6
Total with taxes and fees
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

12. 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
$336 nightly
The price is $374
Nov 9 - Nov 10
Total with taxes and fees
Peregrine's Perch - Cabin Overlooking the River!
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

13. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (56 reviews)
"Very comfortable and cozy. Our family had a great stay here."
United States
bethany c.
$242 nightly
The price is $269
Nov 12 - Nov 13
Total with taxes and fees
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.

14. 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.
$137 nightly
The price is $153
Nov 5 - Nov 6
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

15. 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, (117 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.
$194 nightly
The price is $206
Nov 8 - Nov 9
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (161 reviews)
"Great little spot!"
United States
Shelby W.
$243 nightly
The price is $258
Nov 8 - Nov 9
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

17. 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.
$407 nightly
The price is $431
Nov 11 - Nov 12
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A lakeside setting with wooden chairs and a picnic table, surrounded by lush greenery and trees.

18. 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
$220 nightly
The price is $243
Nov 8 - Nov 9
Total with taxes and fees
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
A playground with swings, a slide, and a fire pit area with chairs.

19. Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
9.8 out of 10, Exceptional, (17 reviews)
"Welcoming and spacious for all invitees and we did not even have a chance to explore all the areas that were surrounding as it was a work related trip but will get out there at some later point for a completely relaxing stay for sure"
United States
Image M.
$422 nightly
The price is $471
Nov 5 - Nov 6
Total with taxes and fees
Glamping Clear Spring Maryland 3-Cabin Campground
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

20. 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.
$200 nightly
The price is $201
Nov 5 - Nov 6
Total with taxes and fees
Bin There Treehouse - A Grain Bin treehouse!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Fairplay Hotel Reviews

Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

10/10 Excellent
"Fantastic"
Marcelo 1-night trip
Posted 6 hours ago
Quality Inn Harpers Ferry - Charles Town

Find out more about Fairplay

Everything you need to know about Fairplay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Fairplay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Fairplay vacation 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 low season months. For more hustle and bustle, you may prefer to visit Fairplay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $206 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Fairplay rentals

At Expedia, we put the best Fairplay vacation 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 vacation.

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 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.