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Fairplay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Fairplay vacation rentals

A room with large windows, wooden floors, and a ceiling fan.

1. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (100 reviews)
"We had a lovely get-away! Really enjoyed ourselves."
United States
Erinn
$313 nightly
The price is $332
Oct 18 - Oct 19
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

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, (18 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
$323 nightly
The price is $334
Oct 18 - Oct 19
Total with taxes and fees
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

3. 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
Oct 20 - Oct 21
Total with taxes and fees
Large Family Home: 5 Mi to Dtwn Hagerstown!
Exterior

4. Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
$295 nightly
The price is $313
Oct 20 - Oct 21
Total with taxes and fees
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

5. 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)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
$437 nightly
The price is $464
Oct 19 - Oct 20
Total with taxes and fees
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

6. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (87 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
$96 nightly
The price is $107
Oct 25 - Oct 26
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
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, (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.
$321 nightly
The price is $357
Oct 26 - Oct 27
Total with taxes and fees
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

8. 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.
$406 nightly
The price is $452
Oct 20 - Oct 21
Total with taxes and fees
Large Family Home: 5 Mi to Dtwn Hagerstown!
A living room with a dining table, chairs, a sofa, and a television.

9. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
$211 nightly
The price is $235
Oct 19 - Oct 20
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

10. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 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.
$333 nightly
The price is $371
Nov 2 - Nov 3
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

11. 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, (76 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$350 nightly
The price is $390
Nov 3 - Nov 4
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

12. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (55 reviews)
"Nice little place. Hosts were very responsive."
United States
Miki M.
$252 nightly
The price is $280
Nov 12 - Nov 13
Total with taxes and fees
Charming Cabin in the Woods with River Access
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

13. 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, (19 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
$426 nightly
The price is $452
Oct 29 - Oct 30
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

14. 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
$324 nightly
The price is $361
Nov 4 - Nov 5
Total with taxes and fees
Peregrine's Perch - Cabin Overlooking the River!
A patio with outdoor furniture, a pool, and a barbecue grill.

15. 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.
$105 nightly
The price is $116
Oct 26 - Oct 27
Total with taxes and fees
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
A playground with swings, a slide, and a fire pit area with chairs.

16. 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.
$445 nightly
The price is $495
Oct 18 - Oct 19
Total with taxes and fees
Glamping Clear Spring Maryland 3-Cabin Campground
A modern bedroom with a large bed, a view of a forest through floor-to-ceiling windows, and a minimalist design.

17. Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
Mercersburg
10.0 out of 10, Exceptional, (28 reviews)
"Great place to unwind and relax."
United States
Candace
$618 nightly
The price is $669
Nov 4 - Nov 5
Total with taxes and fees
Mirror Villas - Modern Retreat with private hot tubs and mountain view
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

18. 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, (116 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.
$244 nightly
The price is $259
Oct 26 - Oct 27
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.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (159 reviews)
"Perfect little house in a great historic location."
United States
Donald K.
$237 nightly
The price is $251
Oct 18 - Oct 19
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
A room with a central island, a ceiling fan, a window with blinds, and a wall-mounted shelf.

20. 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.
$145 nightly
The price is $161
Oct 18 - Oct 19
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
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

Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view

10/10 Excellent
"Excellent"
Kevin 2-night trip
Posted 12 hours ago
Mirror Villas - Modern Retreat with private hot tubs and mountain view

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 $191 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.