A historical reenactment with soldiers in period uniforms, a cannon, and smoke in a grassy field under a cloudy sky.

Fairplay Holiday Rentals

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Our top choices for Fairplay holiday rentals

1. Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Blue Ridge Summit
9.6 out of 10, Exceptional, (21 reviews)
"Great spot close to the wedding venue!!"
United States
Alfred T.
The price is NZ$305
includes taxes & fees
19 Nov - 20 Nov
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

2. Stratton House-Unique Historic District Home-Backs to Culp's Hill-Ski Liberty!

Stratton House-Unique Historic District Home-Backs to Culp's Hill-Ski Liberty!
Gettysburg Historic District
10.0 out of 10, Exceptional, (80 reviews)
"Tidy, comfortable and historical rental property with easy walking distance to shops and restaurants."
United States
Ken L.
The price is NZ$746
includes taxes & fees
29 Nov - 30 Nov
Stratton House-Unique Historic District Home-Backs to Culp's Hill-Ski Liberty!

3. Gray Getaway

Gray Getaway
Gettysburg Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely accommodations- clean and modern as well as being a great location in downtown Gettysburg. Hope to stay again in the future."
United States
Carol M.
The price is NZ$662
includes taxes & fees
1 Dec - 2 Dec
Gray Getaway

4. Rural & Historic Detour Escape w/ Horses On-Site!

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (8 reviews)
"Lovely! Our host was gracious and helpful. Property was ideal for our family getaway. i’m"
United States
Mary F.
The price is NZ$736
includes taxes & fees
14 Nov - 15 Nov
Rural & Historic Detour Escape w/ Horses On-Site!

5. Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!

Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!
Orrtanna
10.0 out of 10, Exceptional, (121 reviews)
"Beautiful, quiet property, and the hosts were great to work with!"
United States
Matthew L.
The price is NZ$246
includes taxes & fees
16 Nov - 17 Nov
Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!

6. 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 traveller
The price is NZ$330
includes taxes & fees
20 Nov - 21 Nov
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

7. Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
10.0 out of 10, Exceptional, (11 reviews)
"I cannot say enough about the wonderful time we had staying at Denise & Mike's lovely cottage. They went above and beyond to make sure our family gathering was perfect...and it truly was. Sitting on the front porch sharing coffee in the a.m. and wine in the evening. Board games, chats and laughter until our bellies ached. Our family spent our much needed reunion sharing long overdue times making more wonderful memories. Upon arrival we found the property even more special than we imagined from...
United States
Julianne L.
The price is NZ$439
includes taxes & fees
22 Nov - 23 Nov
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

8. A "Suite" Place to Crash

A "Suite" Place to Crash
Gettysburg
10.0 out of 10, Exceptional, (96 reviews)
"Awesome place to stay for our Cousin Camp group. Clean & the owners were accommodating & went above & beyond."
United States
Ladd H.
The price is NZ$277
includes taxes & fees
17 Nov - 18 Nov
A "Suite" Place to Crash

9. Blue Getaway

Blue Getaway
Gettysburg Historic District
10.0 out of 10, Exceptional, (22 reviews)
"Great place to stay in Gettysburg - and especially walkable! Would recommend! "
United States
Victoria O.
The price is NZ$672
includes taxes & fees
17 Nov - 18 Nov
Blue Getaway

10. Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is NZ$777
includes taxes & fees
14 Nov - 15 Nov
Rural & Historic Detour Escape w/ Horses On-site!

11. Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Hanover
9.6 out of 10, Exceptional, (7 reviews)
"Great location in downtown Hanover within walking distance of the square where there are various shops and dining options. "
United States
Danna W.
The price is NZ$480
includes taxes & fees
14 Nov - 15 Nov
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

12. Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
8.8 out of 10, Excellent, (15 reviews)
"Place was as described. "
United States
Katie F.
The price is NZ$252
includes taxes & fees
11 Dec - 12 Dec
Cozy studio charming Hanover

13. Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6

Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6
Orrtanna
9.8 out of 10, Exceptional, (18 reviews)
"Just perfect, love this place definitely coming back when I stay in Pennsylvania"
United States
William G.
The price is NZ$542
includes taxes & fees
15 Nov - 16 Nov
Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6

14. The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn

The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn
Orrtanna
9.8 out of 10, Exceptional, (61 reviews)
"Our host was prompt on questions and the house was clean and cute. Our family was able to relax and enjoy the property while on vacation"
United States
Ash Lee S.
The price is NZ$605
includes taxes & fees
16 Nov - 17 Nov
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn

15. Applewood Landing

Applewood Landing
Gettysburg
9.6 out of 10, Exceptional, (20 reviews)
"Beautiful property. Easily accessible to Gettysburg. We all enjoyed the back covered patio and the pool. Would highly recommend! Would stay here again!"
United States
Linda S.
The price is NZ$1,822
includes taxes & fees
1 Dec - 2 Dec
Applewood Landing

16. 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.
The price is NZ$377
includes taxes & fees
15 Nov - 16 Nov
Bin There Treehouse - A Grain Bin treehouse!

17. Homestead Haven | Fire Pit, Pickleball & Fun

Homestead Haven | Fire Pit, Pickleball & Fun
Gettysburg
9.0 out of 10, Wonderful, (17 reviews)
"Clean and neat easy to find great location. Peaceful area quite and relaxing. Beds were very comfortable."
United States
Mary Kay
The price is NZ$885
includes taxes & fees
16 Nov - 17 Nov
Homestead Haven | Fire Pit, Pickleball & Fun

18. Cozy Apartment Near Gettysburg & Chambersburg

Cozy Apartment Near Gettysburg & Chambersburg
Fayetteville
8.0 out of 10, Very good, (1 review)
"The room was very clean, and super close to Caledonia State Park and not far from Gettysburg. It is cozy as described, so on the smaller side, however the price was right and we mainly used the place to sleep and have breakfast only. The host was available when needed and overall we had a great stay."
United States
Taylor M.
The price is NZ$257
includes taxes & fees
10 Dec - 11 Dec
Cozy Apartment Near Gettysburg & Chambersburg

19. Rancher in Mont Alto

Rancher in Mont Alto
Mont Alto
9.8 out of 10, Exceptional, (17 reviews)
"Great place to stay"
United States
Austin B.
The price is NZ$440
includes taxes & fees
17 Nov - 18 Nov
Rancher in Mont Alto

20. Walk to downtown Gettysburg/Civil War home

Walk to downtown Gettysburg/Civil War home
Gettysburg Historic District
10.0 out of 10, Exceptional, (26 reviews)
"Perfect spot close to downtown with plenty of space for our two families."
United States
Heather C.
The price is NZ$1,031
includes taxes & fees
15 Nov - 16 Nov
Walk to downtown Gettysburg/Civil War home
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

Find out more about Fairplay

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Fairplay holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Fairplay. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Fairplay. Seeing all the best attractions is bound to make you fall in love with Fairplay. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Fairplay short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Fairplay?

Yes, there are holiday rentals close to the most popular sights in Fairplay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Fairplay has to offer?

Unique Gettysburg Barn Loft central to Gettysburg and Ski Liberty!: This holiday home rental outside of Fairplay offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Fairplay?

While exploring the area, visit family-friendly sights like Catoctin Wildlife Preserve and Zoo, or get outside and enjoy nature at Union Mills Homestead Park. Gettysburg Allstar Expo Complex and Eisenhower National Historic Site are a couple of places you'll find in the wider area.

What are holiday rentals like in Fairplay?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Fairplay. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family getaway.