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Chewsville Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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
The price is AED 294
AED 788 total
includes taxes & fees
12 Nov - 13 Nov
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
The price is AED 232
AED 259 total
includes taxes & fees
1 Dec - 2 Dec
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.
The price is AED 225
AED 622 total
includes taxes & fees
11 Nov - 12 Nov
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.
The price is AED 165
AED 376 total
includes taxes & fees
17 Nov - 18 Nov
❤️ 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, (118 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 AED 533
AED 1,036 total
includes taxes & fees
28 Nov - 29 Nov
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.
The price is AED 591
AED 801 total
includes taxes & fees
17 Nov - 18 Nov
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
10.0 out of 10, Exceptional, (11 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.
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, (162 reviews)
"Great little spot!"
United States
Shelby W.
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
The price is AED 260
AED 291 total
includes taxes & fees
8 Dec - 9 Dec
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
The price is AED 232
AED 259 total
includes taxes & fees
1 Dec - 2 Dec
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
The price is AED 233
AED 261 total
includes taxes & fees
1 Dec - 2 Dec
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
The price is AED 260
AED 291 total
includes taxes & fees
1 Dec - 2 Dec
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
The price is AED 232
AED 259 total
includes taxes & fees
1 Dec - 2 Dec
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)
"Cute place with a lot of character. Host was very responsive. We enjoyed our sray."
United States
Dawn V.
The price is AED 550
AED 1,160 total
includes taxes & fees
11 Nov - 12 Nov
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.
The price is AED 459
AED 672 total
includes taxes & fees
11 Nov - 12 Nov
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
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.
The price is AED 255
AED 373 total
includes taxes & fees
11 Nov - 12 Nov
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.
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
The price is AED 441
AED 774 total
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AED 275
AED 561 total
includes taxes & fees
11 Nov - 12 Nov
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

Courtyard Marriott Hagerstown

Courtyard Marriott Hagerstown

10/10 Excellent
"Great staff nice clean outside area to hang out, fire pit"
Daniel 1-night trip
Posted 10 hours ago
Courtyard Marriott Hagerstown

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.