Fairplay holiday rentals

We found 101 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Fairplay that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the amenities that you need and want, which might include a hot tub and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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Book a holiday rental for your Fairplay getaway

Learn about the unique charm of Fairplay with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Fairplay

Are you looking for top things to see and do during your stay? Venture out of your cosy holiday rental and experience everything that makes Fairplay a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Big Cork Vineyards (8.6 mi / 13.9 km)
  • Hagerstown Speedway (9.9 mi / 15.9 km)
  • Musket Ridge Golf Course (11 mi / 17.7 km)
  • Whitetail Ski Resort (17.3 mi / 27.8 km)
  • Mason Dixon Dragway (6.1 mi / 9.8 km)
  • Antietam Creek Vineyards (6.3 mi / 10.2 km)

Exploring the natural features in Fairplay

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Fairplay is a great place to get out in nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Crystal Grottoes Caverns (4.5 mi / 7.3 km)
  • Greenbrier State Park (6.6 mi / 10.7 km)
  • Marty Snook County Park (5 mi / 8 km)
  • Morgan's Grove Park (8.9 mi / 14.4 km)
  • Hillside Lake (13.2 mi / 21.2 km)
  • Virginius Island (14.9 mi / 23.9 km)

Travelling to and around Fairplay

The nearest airport is in Hagerstown, MD (HGR-Hagerstown Regional), located 11.7 mi (18.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is 15.8 mi (25.4 km) away.

Frequently asked questions

What is the best area to stay in Fairplay when booking a holiday rental?
When considering a holiday rental in Fairplay, Maryland, the area around the town itself offers a charming blend of tranquillity and easy access to local attractions. Fairplay is located conveniently between the bustling cities of Hagerstown and Frederick, making it an ideal spot for those looking to explore both rural and urban settings.One of the highlights of staying in Fairplay is the proximity to the scenic Antietam National Battlefield, which is just a short drive away. This historic site not only offers a glimpse into the past but also features beautiful walking trails and picnic areas, great for a day of exploration. Additionally, the nearby Catoctin Mountain Park provides ample opportunities for outdoor activities, including hiking and wildlife observation, set against the stunning backdrop of the Appalachian Mountains.The area around Fairplay features a range of holiday rental properties, giving visitors a variety of options to choose from. Whether you prefer a cosy cabin or a spacious home, you can find properties that cater to different group sizes and budgets.
What is the most popular type of holiday rental accomodation in Fairplay?
In Fairplay, holiday houses are the most popular type of holiday rental accommodation, with several available throughout the area. These homes provide a spacious environment, often featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many properties also include outdoor spaces such as decks or gardens, allowing guests to enjoy the scenic surroundings.
Are there pet-friendly house rentals in Fairplay?
In Fairplay, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to bring their furry friends along. Many of these holiday homes offer amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, ensuring a relaxing stay for both pets and their owners.The area is surrounded by picturesque landscapes, providing plenty of outdoor opportunities for pet owners to enjoy. Nearby, you can find parks and walking trails that are ideal for leisurely strolls with pets, allowing for a pleasant blend of relaxation and outdoor adventure.
Are there any remote work holiday rentals in Fairplay?
In Fairplay, Maryland, there are several remote work holiday rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties come equipped with amenities essential for remote work, such as reliable internet access through third-party services, ensuring that you can stay connected while enjoying your surroundings.The area is known for its picturesque landscapes and proximity to outdoor activities, providing a refreshing backdrop for working remotely. Guests can expect comfortable living spaces, often featuring dedicated work areas and relaxing environments to help maintain productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Fairplay?
In Fairplay, popular rental amenities cater to pet lovers, with many properties allowing dogs and other pets, including service animals. Travellers can expect reliable WiFi in most rentals, ensuring they stay connected during their stay.
What are the top attractions in Fairplay?
In Fairplay, Maryland, visitors can enjoy a blend of natural beauty and historical sites. The area is close to the scenic Antietam National Battlefield, where history enthusiasts can explore the pivotal Civil War site and its well-preserved landscape. Nearby, the Potomac River offers opportunities for outdoor activities such as fishing, kayaking, and hiking along its picturesque banks.For those interested in local culture, Fairplay is situated near the charming town of Shepherdstown, West Virginia, known for its vibrant arts scene, quaint shops, and the historic Shepherd University. The surrounding countryside is ideal for leisurely drives and exploring local vineyards, providing a superb backdrop for a relaxing getaway.Additionally, the C&O Canal National Historical Park runs nearby, offering trails for hiking and biking, making it a great spot for outdoor enthusiasts.
Are all fees included in the Fairplay holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Fairplay holiday homes with parking?
Stayz offers a wide selection of holiday homes in Fairplay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Fairplay holiday homes?
You can find great discounts on holiday homes in Fairplay on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Fairplay holiday home booking on Stayz?
To find Fairplay holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Fairplay?
A long-stay holiday home in Fairplay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Fairplay holiday home?
Book your Fairplay holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Fairplay?
Prices for holiday homes in Fairplay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Fairplay to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.