Fountainhead-Orchard Hills Holiday Rentals

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Holiday Rentals in Fountainhead-Orchard Hills

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (85)
"My husband and I were beyond thrilled with this property. Absolutely incredible and are looking forward to visiting again!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (47)
"Excellent little cabin right on the river and close to DT Sheperdstown which is a great town."
The price is AU$172
includes taxes & fees
9 Dec - 10 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Antietam Creek - Quiet 2 Bedroom Cabin

9.4 out of 10, Exceptional, (76)
"We were visiting with family in Boonsboro and arrived late in the evening and left by 9am, but everything was there that we would have needed for a longer stay, which we have planned for Thanksgiving. Kitchen was very well equipped, the space was inviting, the beds were comfy and the view out the back was great, Looking forward to our return!"
The price is AU$520
includes taxes & fees
1 Dec - 2 Dec
Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Toll House~ an historic waterfront cabin

9.8 out of 10, Exceptional, (68)
"We just needed to get out of the city for a night and this was a perfect spot. Cute, comfortable, and with pretty much any amenity you could need. "
The price is AU$441
includes taxes & fees
1 Dec - 2 Dec
Antietam Toll House~ an historic waterfront cabin

Time to plan that fall getaway to the mountains! Enjoy a bit of time away

10.0 out of 10, Exceptional, (282)
"Loved it! Very convenient to Gettysburg (~15 minutes), nestled in the woods and private. Beautiful cabin and well equipped. Will definitely go there again. "
Time to plan that fall getaway to the mountains! Enjoy a bit of time away

Traveling to the area for work, we offer discounted rates for long term rentals.

10.0 out of 10, Exceptional, (13)
"We enjoyed our stay here, the house was very comfortable and well-appointed. We loved the fireplace, the lights on the deck, and were happy it was stocked with games -- we had fun asking each other Trivia questions. We also got to see a deer wander onto the lower part of the property. Would definitely recommend & would stay there again."
The price is AU$206
includes taxes & fees
29 Nov - 30 Nov
Traveling to the area for work, we offer discounted rates for long term rentals.

Waterfront Cabin overlooking the Potomac River W/ Hot Tub

9.8 out of 10, Exceptional, (48)
"Super pleased with everything. Enjoyed our stay so. Very much. Would love to come back sometime. "
The price is AU$457
includes taxes & fees
2 Dec - 3 Dec
Waterfront Cabin overlooking the Potomac River W/ Hot Tub

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

9.8 out of 10, Exceptional, (50)
"The place was adorable. The view was amazing!"
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

9.4 out of 10, Exceptional, (203)
"We had an amzing stay. The cabin is perfect."
Cozy streamside cabin, convenient to Ski Liberty and Gettysburg

Historic & Cozy ~ Near Antietam Battle & WhiteTail

10.0 out of 10, Exceptional, (25)
"Traveling from Illinois to New Hampshire for our road trip. This Vrbo in Hagerstown Maryland was in a beautiful historic district and the inside was absolutely beautiful. We did climb the 4 flights of stairs with 2 large suit cases which was not fun but it was a great way to stay in shape at 60 😂. Inside was so clean and adorable with the original floors, yet updated kitchen & living area. The bedrooms were very cozy and comfortable. The bathroom was large with a huge walk in shower and Amazing...
Historic & Cozy ~ Near Antietam Battle & WhiteTail

Serene Log Cabin Nestled Among the Battlefields

8.2 out of 10, Very good, (25)
"Quaint adorable cabin nestled next to battlefields and short drive to Harpers Ferry. Beautiful deck in back overlooking woods. We hiked at various lookouts and did the ranger talk in town (highly recommend). Magical 3 day 2 nights. Completely relaxed! "
Serene Log Cabin Nestled Among the Battlefields

Lake House w/ Pool and King Bed, Fishing - Dogs OK

9.4 out of 10, Exceptional, (20)
"The water quality was my only complaint. It was extra hard."
Lake House w/ Pool and King Bed, Fishing - Dogs OK

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

9.6 out of 10, Exceptional, (87)
"Quaint little getaway for the night. Especially beautiful in autumn with the foliage and the season decorations inside the home! "
The price is AU$348
includes taxes & fees
1 Dec - 2 Dec
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Antietam Look Out - Incredible Sunset Views!

10.0 out of 10, Exceptional, (16)
"This property has a beautiful, unobstructed view of Antietam. We were an extended family group of 8. The house was very well laid out for an adults and kids with two living spaces. The house was updated, very clean and nicely decorated. It was well stocked in most areas. The only problem was there were no extra towels (only 1 per person) and no extra blankets. The beds only had a light weight comforter and it was cold at night. "
The price is AU$1,242
includes taxes & fees
26 Dec - 27 Dec
Antietam Look Out - Incredible Sunset Views!

WATERFRONT CABIN PRIVATE BEACH HOT TUB FIRE RING FISH HIKE KAYAK

9.8 out of 10, Exceptional, (22)
"We loved this cabin! It had many amenities that other properties don’t have. Very clean!! We will be returning!"
WATERFRONT CABIN PRIVATE BEACH HOT TUB FIRE RING FISH HIKE KAYAK

Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

10.0 out of 10, Exceptional, (9)
"Clean and welcoming home. No complaints."
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

Hollow Hideaway is perfect for your holiday stay!

10.0 out of 10, Exceptional, (30)
"We spent two nights at the home. It was exactly what we needed. The home was immaculate. The beds and linens were luxurious. There was a cute amenities kit in each bedroom - such a nice, extra touch. The home is off of the beaten path so very peaceful. The gas firepit on the covered porch was perfect since we could not use the wood firepit due to drought. The decor was tasteful and restful. The kitchen was well stocked. . We were happy to meet sweet Ellie. She joined us a few times during our...
Hollow Hideaway is perfect for your holiday stay!

Historic Breeches Pocket- Immaculate, Hand-built Log Cabin house- Gettysburg; DC

10.0 out of 10, Exceptional, (169)
"This beautiful home was built by the owners and is tastefully decorated as well as nicely maintained. The location makes it extremely convenient for day trips to surrounding towns such as Frederick, Harper's Ferry and Gettysburg. The home is comfortable and can easily accommodate a large group. The hosts are very responsive. We enjoyed our stay and would rebook if we were to return to the area."
Historic Breeches Pocket- Immaculate, Hand-built Log Cabin house- Gettysburg; DC

Scenic Mountaintop Villa with Free WiFi & Pool

6.0 out of 10, (4)
"The property manager was outstanding, she communicated with me in a professional and courteous fashion. The house was perfect for our group size."
Scenic Mountaintop Villa with Free WiFi & Pool

Pool, Hot Tub, and Fun for all!

10.0 out of 10, Exceptional, (12)
"The host was very attentive and gave great suggestions for things to do in the area based off our interests. The house was clean, and comfortable. Lots of extras to enjoy. "
The price is AU$759
includes taxes & fees
1 Dec - 2 Dec
Pool, Hot Tub, and Fun for all!
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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Other types of properties in Fountainhead-Orchard Hills you may be interested in

Hampton Inn Hagerstown-I-81

2.5 star property
9.4 out of 10, Exceptional, (1053)
"The staff personal were fabulous!"
The price is AU$212
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn Hagerstown-I-81

Country Inn & Suites by Radisson, Hagerstown, MD

3.0 star property
8.4 out of 10, Very good, (1167)
"The room was very clean and the staff very welcoming. "
The price is AU$168
includes taxes & fees
8 Dec - 9 Dec
Country Inn & Suites by Radisson, Hagerstown, MD

Super 8 by Wyndham Hagerstown/Halfway Area

2.0 star property
8.4 out of 10, Very good, (1072)
"It's a budget motel. It's well kept considering. The staff is helpful and friendly. It's supposedly going to get renovated in the near-term. Breakfast is much better than most budget places that offer breakfast items. We're repeat customers."
The price is AU$109
includes taxes & fees
29 Nov - 30 Nov
Super 8 by Wyndham Hagerstown/Halfway Area
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Fountainhead-Orchard Hills?

Yes, there are holiday rentals close to the most popular sights in Fountainhead-Orchard Hills, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Fountainhead-Orchard Hills has a good selection of restaurants. Make sure you have time to check out the live music and sporting events during your trip.

What are some of the best holiday rentals that Fountainhead-Orchard Hills has to offer?

Lake House w/ Pool and King Bed, Fishing - Dogs OK: This holiday home rental outside of Fountainhead-Orchard Hills is located on a lake, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Fountainhead-Orchard Hills?

Explore the area and family-friendly sights such as Hagerstown Roundhouse Museum, or get out into nature at a spot like Greenbrier State Park. In the wider area, you’ll find Pennsylvania Dutch Market and Maryland Theater.

What’s a holiday rental in Fountainhead-Orchard Hills like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Fountainhead-Orchard Hills. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a small group gathering.