Pen Mar Holiday Rentals

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Holiday Rentals in Pen Mar

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Waynesboro
9.8 out of 10, Exceptional, (90)
"The Toll House was clean, had all the amenities advertised, and host had great communication. Very nice to have a fenced yard for my small dog to roam. I recommend this to others! "
United States
Sharon
The price is AU$343
includes taxes & fees
7 Dec - 8 Dec
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Cozy Fairfield Escape Near Historic Sites

3.0 star property
Fairfield
The price is AU$421
includes taxes & fees
8 Dec - 9 Dec
Cozy Fairfield Escape Near Historic Sites

Birch Cabin at Hunting Creek Hideaway

Thurmont
9.8 out of 10, Exceptional, (18)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
The price is AU$211
includes taxes & fees
14 Dec - 15 Dec
Birch Cabin at Hunting Creek Hideaway

Visiting the area on a work assignment. Check out our multi day discounts.

Greencastle
10.0 out of 10, Exceptional, (45)
"Nice stay for a weekend! "
United States
Breezy M.
The price is AU$201
includes taxes & fees
7 Dec - 8 Dec
Visiting the area on a work assignment. Check out our multi day discounts.

Lily Pad - Tiny Home at Mane & Co. / Free Parking

2.0 star property
Chambersburg
10.0 out of 10, Exceptional, (1)
The price is AU$350
includes taxes & fees
15 Dec - 16 Dec
Lily Pad - Tiny Home at Mane & Co. / Free Parking

The Mane & Co - No. 5

2.0 star property
Chambersburg
9.4 out of 10, Exceptional, (3)
"Beautifully modern motel with great amenities and a comfortable bed. The kitchenette was convenient and the bathroom felt luxurious."
United States
Jennifer Z.
The price is AU$311
includes taxes & fees
16 Dec - 17 Dec
The Mane & Co - No. 5

The Mane & Co - No. 4

Chambersburg
10.0 out of 10, Exceptional, (2)
"Loved the property & the management was very helpful!"
United States
Tonya
The price is AU$309
includes taxes & fees
4 Jan - 5 Jan 2026
The Mane & Co - No. 4

Charming in-law suite. The open-concept living area welcomes you.

Blue Ridge Summit
9.4 out of 10, Exceptional, (11)
"Very restful very accommodating and very helpful ownerd"
United States
Donna B.
The price is AU$375
includes taxes & fees
28 Dec - 29 Dec
Charming in-law suite. The open-concept living area welcomes you.

Cozy Loft Retreat- Walk to Liberty Mountain Resort

Fairfield
10.0 out of 10, Exceptional, (14)
"So cozy and comfortable. Great location and wonderful host. "
United States
Amy S.
The price is AU$375
includes taxes & fees
12 Dec - 13 Dec
Cozy Loft Retreat- Walk to Liberty Mountain Resort

The Study on Main Located on the Square!

Chambersburg
9.6 out of 10, Exceptional, (11)
"We enjoyed our stay and the location of the apartment."
United States
Danielle O.
The price is AU$397
includes taxes & fees
16 Dec - 17 Dec
The Study on Main Located on the Square!

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Myersville
9.4 out of 10, Exceptional, (110)
"Alot of choices for food and snacks within walking distance. "
United States
Cherilyn H.
The price is AU$451
includes taxes & fees
16 Dec - 17 Dec
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Beautiful Mansion in the Country & Wedding Venue

Waynesboro
9.8 out of 10, Exceptional, (9)
"The stay and place was awesome and my family and I will definitely be booking again "
United States
Comedy C.
The price is AU$4,180
includes taxes & fees
15 Dec - 16 Dec
Beautiful Mansion in the Country & Wedding Venue

Galloping Getaway on the rolling hills of GemStone Stable

Hagerstown
10.0 out of 10, Exceptional, (14)
"Perfect for us as we visited family."
United States
Felicia H.
The price is AU$283
includes taxes & fees
15 Dec - 16 Dec
Galloping Getaway on the rolling hills of GemStone Stable

Historic & Cozy ~ Near Antietam Battle & WhiteTail

Hagerstown
10.0 out of 10, Exceptional, (32)
"We loved the ambiance of this place. It was in a great neighborhood, and its location was perfect for our needs."
United States
Michelle D.
The price is AU$397
includes taxes & fees
8 Dec - 9 Dec
Historic & Cozy ~ Near Antietam Battle & WhiteTail

3-bedroom townhome in charming Hagerstown with AC, WiFi

Hagerstown
6.0 out of 10, (1)
"The inside was very clean, outside was a mess. Location was bad, on a busy street and a busy railway."
United States
mark C.
The price is AU$328
includes taxes & fees
16 Dec - 17 Dec
3-bedroom townhome in charming Hagerstown with AC, WiFi

The Cutest Loft on Main St!

Chambersburg
10.0 out of 10, Exceptional, (11)
"Excellent location for downtown festivals and restaurants!"
United States
Dawn
The price is AU$350
includes taxes & fees
16 Dec - 17 Dec
The Cutest Loft on Main St!

The Boho Penthouse on Main

Chambersburg
9.2 out of 10, Wonderful, (17)
"Fantastic place for the night. Clean with a great restaurant within walking distance."
United States
Heather B.
The price is AU$351
includes taxes & fees
5 Jan - 6 Jan 2026
The Boho Penthouse on Main

Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D

2.0 star property
Hagerstown
10.0 out of 10, Exceptional, (1)
"The host is very responsive and helpful. The amenities were fantastic. The condo is super clean, well maintained and even has super soft towels and a little snack bar with coffee, tea, and chips. Very impressed with the host and the amenities. Location to dining and nightlife is great fir a family. Free parking also a great bonus. Wonderful place to stay! "
United States
Paul F.
The price is AU$374
includes taxes & fees
16 Dec - 17 Dec
Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D

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, (54)
"Very nice stay. Close to everything and great amenities. Will definitely stay again if we are back in the area"
United States
Cammeron F.
The price is AU$533
includes taxes & fees
18 Dec - 19 Dec
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn

Charming getaway, sleeps 9, easy access, 8 miles to battlefields, pet friendly.

Orrtanna
The price is AU$396
includes taxes & fees
8 Dec - 9 Dec
Charming getaway, sleeps 9, easy access, 8 miles to battlefields, pet friendly.
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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Find out more about Pen Mar

Everything you need to know about Pen Mar holiday rentals

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

Pen Mar holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pen Mar. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pen Mar holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pen Mar holiday rentals we have selected for you start as low as AU$201 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pen Mar rentals

At Expedia, we put the best Pen Mar holiday 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 Pen Mar 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 Pen Mar holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pen Mar. 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 holiday rentals in Pen Mar?

Yes, there are holiday rentals close to the most popular sights in Pen Mar, 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 Pen Mar has to offer?

Visit our charming cottage this Fall & Winter. Enjoy the Scenery & Ski Slopes.: This holiday home rental outside of Pen Mar is located in the mountains, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

What can I see and do in Pen Mar?

Explore the area and family-friendly sights such as Catoctin Wildlife Preserve and Zoo, or get out into nature at a spot like Pen Mar Park. In the wider area, you’ll find South Mountain State Park and Cunningham Falls State Park.

What are holiday rentals like in Pen Mar?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pen Mar. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family trips or small group gatherings.