Chewsville Vacation Rentals

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Our top choices for Chewsville vacation rentals

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
9.8 out of 10, Exceptional, (65)
"We truly loved this location and definitely will be back!"
United States
Astrid
$96 nightly
The price is $106
Dec 17 - Dec 18
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River

Bring Your Own Boat - Meticulously restored house on the Potomac River

Hedgesville
10.0 out of 10, Exceptional, (9)
"Cute little house that my husband and I enjoyed for the weekend. Great location close to Martinsburg. It had everything we needed for our weekend The host communicated well, we had no issues, and we would definitely stay here again. Thank you!"
United States
Jennifer E.
$145 nightly
The price is $161
Dec 11 - Dec 12
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River

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

Middletown
9.6 out of 10, Exceptional, (110)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
$165 nightly
The price is $175
Dec 11 - Dec 12
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Cozy Pine Tree Nest

Frederick
9.4 out of 10, Exceptional, (11)
"Really nice apartment was just what we wanted for a weekend while here to run the JFK 50 miler"
United States
David S.
$171 nightly
The price is $181
Dec 29 - Dec 30
Total with taxes and fees
Cozy Pine Tree Nest

Cozy Fairfield Escape Near Historic Sites

3.0 star property
Fairfield
Cozy Fairfield Escape Near Historic Sites

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

Waynesboro
9.8 out of 10, Exceptional, (91)
"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
$214 nightly
The price is $236
Dec 15 - Dec 16
Total with taxes and fees
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

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.
$131 nightly
The price is $138
Dec 15 - Dec 16
Total with taxes and fees
Birch Cabin at Hunting Creek Hideaway

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

Middletown
10.0 out of 10, Exceptional, (139)
"Love the place will book again"
United States
WAYNE M.
$214 nightly
The price is $227
Dec 11 - Dec 12
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown

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

Keedysville
9.8 out of 10, Exceptional, (65)
"Great stay! We would book again. "
United States
Sam F.
$327 nightly
The price is $364
Dec 11 - Dec 12
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Sharpsburg
10.0 out of 10, Exceptional, (39)
"We had an amazing time - lots of walks and places to see - very historical - winery right next door which was an added bonus - accommodation was everything we needed and more - look out for a friendly cat that paid a few visits - thank you Jordan for a great time and will definitely come back to the area"
United Kingdom
Jo W.
$282 nightly
The price is $314
Dec 14 - Dec 15
Total with taxes and fees
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Antietam Look Out - Incredible Sunset Views!

Keedysville
9.8 out of 10, Exceptional, (34)
"The property was perfect for our family. It was well equipped with all the kitchen necessities. plenty of space, bedrooms, and bathrooms to accommodate 7 adults and a 1 yr old. Great location for seeing sites. "
United States
Barbara B.
$393 nightly
The price is $437
Dec 14 - Dec 15
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!

Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81

Hedgesville
7.4 out of 10, Good, (3)
"Nice clean property. It was spacious and comfortable. "
United States
Diane G.
$92 nightly
The price is $102
Dec 11 - Dec 12
Total with taxes and fees
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81

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.
$119 nightly
The price is $131
Dec 11 - Dec 12
Total with taxes and fees
Visiting the area on a work assignment. Check out our multi day discounts.

Peregrine's Perch - Cabin Overlooking the River!

Falling Waters
9.6 out of 10, Exceptional, (21)
"Very beautiful place to stay, my family and I enjoyed everything that was offered and very scenic great for pictures and overall a great trip with the family "
United States
Blas G.
Peregrine's Perch - Cabin Overlooking the River!

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.
$189 nightly
The price is $208
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming in-law suite. The open-concept living area welcomes you.

Charming Cabin in the Woods with River Access

Shepherdstown
9.6 out of 10, Exceptional, (40)
"My family enjoyed our stay at the cabin including having access to the river for morning coffee and playing board games in the evening after a day of tubing. The drive to the cabin was beautiful with lots of deer sightings. "
United States
Leana H.
$226 nightly
The price is $252
Dec 29 - Dec 30
Total with taxes and fees
Charming Cabin in the Woods with River Access

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.
$279 nightly
The price is $296
Dec 17 - Dec 18
Total with taxes and fees
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.
$1,997 nightly
The price is $2,206
Dec 11 - Dec 12
Total with taxes and fees
Beautiful Mansion in the Country & Wedding Venue

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.
$233 nightly
The price is $260
Dec 11 - Dec 12
Total with taxes and fees
Historic & Cozy ~ Near Antietam Battle & WhiteTail

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.
$222 nightly
The price is $245
Dec 12 - Dec 13
Total with taxes and fees
Cozy Loft Retreat- Walk to Liberty Mountain Resort
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 Chewsville Hotel Reviews

Find out more about Chewsville

Everything you need to know about Chewsville vacation rentals

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

Chewsville vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $106 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chewsville rentals

At Expedia, we put the best Chewsville vacation 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 Chewsville 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 Chewsville vacation.

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

Are there vacation rentals in Chewsville?

Yes, you can find vacation rentals close to well known points of interest in Chewsville, or you can select a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Chewsville has to offer?

Exclusive Wooded Chalet w Magnificent River Views: Visitors like this Chewsville vacation home rental. It offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Chewsville?

Explore the area and family-friendly sights such as Catoctin Wildlife Preserve and Zoo, or get out into nature at a spot like Greenbrier State Park. Pennsylvania Dutch Market and Maryland Theater are a couple of places you'll find in the larger area.

What are vacation rentals like in Chewsville?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Chewsville. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a small group gathering.