Chewsville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chewsville vacation rentals

A lakeside setting with wooden chairs and a picnic table, surrounded by lush greenery and trees.

1. 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 traveler
$189 nightly
The price is $209
Nov 10 - Nov 11
Total with taxes and fees
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

2. Bright 2-Bed ADA Room|Free Parking

Bright 2-Bed ADA Room|Free Parking
Hagerstown
10.0 out of 10, Exceptional, (3 reviews)
"Bed firm yet cozy providing restful support during our stay of one night."
United States
Anonymous traveler
$63 nightly
The price is $71
Dec 1 - Dec 2
Total with taxes and fees
Bright 2-Bed ADA Room|Free Parking
A house with a covered porch, two wicker chairs, a welcome sign, and a hanging flower basket.

3. 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.
$149 nightly
The price is $165
Nov 8 - Nov 9
Total with taxes and fees
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

4. ❤️ 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.
$86 nightly
The price is $96
Nov 15 - Nov 16
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

5. 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.
$190 nightly
The price is $201
Nov 10 - Nov 11
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

6. 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.
$211 nightly
The price is $212
Nov 10 - Nov 11
Total with taxes and fees
Bin There Treehouse - A Grain Bin treehouse!
A living room with a stone wall, a wooden staircase, a dark-colored sofa with cushions, and a small shelf with model buildings.

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
9.8 out of 10, Exceptional, (10 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.
$222 nightly
The price is $235
Nov 9 - Nov 10
Total with taxes and fees
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (161 reviews)
"Great little spot!"
United States
Shelby W.
$236 nightly
The price is $250
Nov 8 - Nov 9
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

9. Spacious King Bed | Free Parking

Spacious King Bed | Free Parking
Hagerstown
10.0 out of 10, Exceptional, (3 reviews)
"Checking in took no time, plus blackout curtains provided just the right setting for sleeping soundly at night."
United States
Anonymous traveler
$71 nightly
The price is $79
Dec 1 - Dec 2
Total with taxes and fees
Spacious King Bed | Free Parking
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

10. Spacious 2-Bed Queen | Free Parking

Spacious 2-Bed Queen | Free Parking
Hagerstown
10.0 out of 10, Exceptional, (2 reviews)
"Quiet place with comfy beds. Not too fancy but better than some cheaper options nearby."
United States
Anonymous traveler
$63 nightly
The price is $71
Dec 1 - Dec 2
Total with taxes and fees
Spacious 2-Bed Queen | Free Parking
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

11. Cozy 2-bed ADA Room | Free Parking

Cozy 2-bed ADA Room | Free Parking
Hagerstown
10.0 out of 10, Exceptional, (2 reviews)
"Convenient parking spot near entrance added ease to arrivals and departures every day of our trip!"
United States
Anonymous traveler
$63 nightly
The price is $71
Dec 1 - Dec 2
Total with taxes and fees
Cozy 2-bed ADA Room | Free Parking
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

12. Cozy King Bed | Free Wifi & Parking

Cozy King Bed | Free Wifi & Parking
Hagerstown
10.0 out of 10, Exceptional, (2 reviews)
"Having both a fridge and microwave right in the room turned out very useful!"
United States
Anonymous traveler
$71 nightly
The price is $79
Dec 1 - Dec 2
Total with taxes and fees
Cozy King Bed | Free Wifi & Parking
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

13. Clean 2-bed Queen | Free Parking

Clean 2-bed Queen | Free Parking
Hagerstown
8.8 out of 10, Excellent, (3 reviews)
"We liked how the double bed felt solid but soft enough for a restful night's sleep together after long drives each day"
United States
Anonymous traveler
$63 nightly
The price is $71
Dec 1 - Dec 2
Total with taxes and fees
Clean 2-bed Queen | Free Parking
A wooden cabin with a patio area, outdoor seating, and a fire pit.

14. 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.
$294 nightly
The price is $303
Nov 8 - Nov 9
Total with taxes and fees
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A living room with a sofa, a TV mounted on the wall, and a large sliding glass door leading to a garden.

15. Galloping Getaway on the rolling hills of GemStone Stable

Galloping Getaway on the rolling hills of GemStone Stable
Hagerstown
10.0 out of 10, Exceptional, (33 reviews)
"We loved staying here. Beautiful views, great communication with Tammie, and very clean. Definitely will stay again!"
United States
Haley H.
$160 nightly
The price is $179
Nov 8 - Nov 9
Total with taxes and fees
Galloping Getaway on the rolling hills of GemStone Stable
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

16. Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (24 reviews)
"Relaxing, close to all."
United States
Valarie
$327 nightly
The price is $365
Nov 9 - Nov 10
Total with taxes and fees
Peregrine's Perch - Cabin Overlooking the River!
A patio with outdoor furniture, a pool, and a barbecue grill.

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

Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Hedgesville
9.0 out of 10, Wonderful, (9 reviews)
"Nice clean property. It was spacious and comfortable. "
United States
Diane G.
$89 nightly
The price is $99
Nov 10 - Nov 11
Total with taxes and fees
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

18. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (46 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.
$350 nightly
The price is $391
Nov 18 - Nov 19
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
A living room with a dining table, chairs, a sofa, and a television.

19. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
$196 nightly
The price is $219
Nov 9 - Nov 10
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A room with a central island, a ceiling fan, a window with blinds, and a wall-mounted shelf.

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

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"Great little place to stay."
United States
Shannon W.
$134 nightly
The price is $150
Nov 8 - Nov 9
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
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

An indoor swimming pool with clear water, surrounded by lounge chairs and a sunset view through a large window.
Hampton Inn Hagerstown-I-81

Hampton Inn Hagerstown-I-81

Hampton Inn Hagerstown-I-81
Hagerstown

10/10 Excellent

This hotel was very clean. I reviewed a lot of hotels in the area. It took me awhile to find one with good reviews. I was very happy with this hotel. They had a good breakfast as well. Friendly staff.
United States
Anonymous traveler
Reviewed July 16, 2021
Hampton Inn Hagerstown-I-81

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 $70 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?

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.: Visitors like this Chewsville vacation home rental. It is located in the mountains and has a fireplace, a patio, and air-conditioning 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Chewsville?

Explore the area and family-friendly sights such as Greencastle Coffee Roasters, 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.

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