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Appletown Holiday Rentals

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Our top choices for Appletown holiday rentals

1. 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, (117 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.
The price is NZ$366
includes taxes & fees
26 Oct - 27 Oct
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is NZ$188
includes taxes & fees
1 Nov - 2 Nov
❤️ Secluded 1940s Romantic Tiny House on the River

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (160 reviews)
"Great little spot!"
United States
Shelby W.
The price is NZ$552
includes taxes & fees
24 Nov - 25 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown

4. 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.
The price is NZ$385
includes taxes & fees
26 Oct - 27 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance

5. 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, (19 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is NZ$574
includes taxes & fees
16 Nov - 17 Nov
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

6. Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (70 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
The price is NZ$314
includes taxes & fees
25 Oct - 26 Oct
Cozy Getaway near Harper`s Ferry, C&O & Potomac

7. 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.
The price is NZ$719
includes taxes & fees
4 Nov - 5 Nov
Antietam Look Out - Incredible Sunset Views!

8. Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (14 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
Huge 1br apt, baby-friendly, dogs, walkable downtown

9. 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.
The price is NZ$546
includes taxes & fees
26 Oct - 27 Oct
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

10. 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.
The price is NZ$478
includes taxes & fees
24 Nov - 25 Nov
Charming Cabin in the Woods with River Access

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
The price is NZ$758
includes taxes & fees
3 Nov - 4 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

12. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (101 reviews)
"The cabin was clean, spacious, and"
United States
Daniel
The price is NZ$612
includes taxes & fees
25 Oct - 26 Oct
Antietam Creek - Quiet 2 Bedroom Cabin

13. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
9.0 out of 10, Wonderful, (4 reviews)
"My friends and I had a wonderful time here for Labor Day! Quiet and a great location for all sorts of activities."
United States
Nick W.
Antietam House Historic Sharpsburg Retreat

14. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
The price is NZ$386
includes taxes & fees
28 Oct - 29 Oct
Cozy, dog-friendly, downtown

15. Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (29 reviews)
"really nice place"
United States
David R.
The price is NZ$345
includes taxes & fees
25 Oct - 26 Oct
Beautiful, Historic, Hiking, Biking and C&O Canal

16. Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
10.0 out of 10, Exceptional, (74 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is NZ$453
includes taxes & fees
26 Oct - 27 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

17. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is NZ$441
includes taxes & fees
28 Oct - 29 Oct
Cozy Downtown Cabin - Family Friendly

18. Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (13 reviews)
"Very friendly host who made communications easy. We left our iPad behind and they called us right away. The apartment was large, beds were comfortable, and the bathroom renovation was beautiful with a great shower. It is about a block from the C&O trail plus free parking on the property."
United States
Kelly
The price is NZ$431
includes taxes & fees
25 Oct - 26 Oct
Historic Getaway near C&O Canal, hiking and biking

19. Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
10.0 out of 10, Exceptional, (54 reviews)
"Great lodging and communicative host"
United States
Peggy D.
The price is NZ$494
includes taxes & fees
28 Oct - 29 Oct
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

20. Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Harpers Ferry
9.2 out of 10, Wonderful, (56 reviews)
"We had a wonderful stay: The place was adorable, spotless, and had everything we needed for a relaxing getaway. It was cozy, well-maintained, and in a great location for exploring Harper’s Ferry. We’re staying here again in a couple months!"
United States
Hannah P.
The price is NZ$404
includes taxes & fees
25 Oct - 26 Oct
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
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 Appletown Hotel Reviews

Find out more about Appletown

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 Appletown 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 Appletown. 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 Appletown. Seeing all the best attractions is bound to make you fall in love with Appletown. 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 Appletown short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Appletown?

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

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This holiday home rental outside of Appletown is located in the mountains, and has a patio, a BBQ 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 Appletown?

Explore the area and family-friendly sights such as Hagerstown Roundhouse Museum, or get out into nature at a spot like Crystal Grottoes Caverns. Big Cork Vineyards and Greenbrier State Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Appletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Appletown. Holiday rentals offer extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.