Chewsville Vacation Rentals

Dates

November 2026

December 2026

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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.

Waynesboro

Anonymous traveler

$80 nightly

12 Nov - 13 Nov

Total with taxes and fees

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

Hagerstown

Anonymous traveler

$63 nightly

1 Dec - 2 Dec

Total with taxes and fees

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.

Blue Ridge Summit

Alfred T.

$61 nightly

8 Nov - 9 Nov

Total with taxes and fees

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

Shepherdstown

Dennis C.

$41 nightly

15 Nov - 16 Nov

Total with taxes and fees

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.

Middletown

Cindy B.

$100 nightly

15 Nov - 16 Nov

Total with taxes and fees

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!

Washington County

Abby G.

$161 nightly

12 Nov - 13 Nov

Total with taxes and fees

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.

Highfield-Cascade

"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...

Julianne L.

$111 nightly

9 Nov - 10 Nov

Total with taxes and fees

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

Middletown

Shelby W.

$95 nightly

8 Nov - 9 Nov

Total with taxes and fees

9. Spacious King Bed | Free Parking

Hagerstown

Anonymous traveler

$71 nightly

1 Dec - 2 Dec

Total with taxes and fees

10. Spacious 2-Bed Queen | Free Parking

Hagerstown

Anonymous traveler

$63 nightly

1 Dec - 2 Dec

Total with taxes and fees

11. Cozy 2-bed ADA Room | Free Parking

Hagerstown

Anonymous traveler

$63 nightly

1 Dec - 2 Dec

Total with taxes and fees

12. Cozy King Bed | Free Wifi & Parking

Hagerstown

Anonymous traveler

$71 nightly

1 Dec - 2 Dec

Total with taxes and fees

13. Clean 2-bed Queen | Free Parking

Hagerstown

Anonymous traveler

$63 nightly

1 Dec - 2 Dec

Total with taxes and fees

A wooden cabin with a patio area, outdoor seating, and a fire pit.

14. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Boonsboro

A D.

$150 nightly

8 Nov - 9 Nov

Total with taxes and fees

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

Hagerstown

Haley H.

$125 nightly

8 Nov - 9 Nov

Total with taxes and fees

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!

Falling Waters

Valarie

$100 nightly

9 Nov - 10 Nov

Total with taxes and fees

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

Hedgesville

Diane G.

$70 nightly

9 Nov - 10 Nov

Total with taxes and fees

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!

Keedysville

Melisa T.

$106 nightly

18 Nov - 19 Nov

Total with taxes and fees

A living room with a dining table, chairs, a sofa, and a television.

19. Quaint Mini Cottage in Shepherdstown - Walking Distance

Shepherdstown

Abigail

$132 nightly

9 Nov - 10 Nov

Total with taxes and fees

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

Hedgesville

Shannon W.

$75 nightly

8 Nov - 9 Nov

Total with taxes and fees

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Find vacation rentals that suit your style

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

Hagerstown

10/10 Excellent

Anonymous traveler

An outdoor patio with wicker furniture, a stone fire pit, and a view of the surrounding neighborhood.

Home2 Suites BY Hilton Hagerstown

Hagerstown

10/10 Excellent

Michael

A hotel with a large entrance, a sign reading "Springhill Suites by Marriott," and an American flag.

Springhill Suites by Marriott Hagerstown

Hagerstown

10/10 Excellent

Very impressive breakfast. Options for anyone on any diet. Never seen a continental breakfast include so many choices. The scrambled eggs with choice of adding fresh spinach, shredded cheddar cheese, salsa and 3 hot sauce options was right up my alley. Also enjoyed delicious Canadian turkey bacon, fresh fruit a some yogurt. They had oatmeal bar with several topping options, make your own waffles and really so much more. Everything clean and well maintained. Traveled with baby and asked if I...

Sara

A Courtyard by Marriott hotel with a modern design, multiple floors, and a parking area in front.

Courtyard Marriott Hagerstown

Hagerstown

10/10 Excellent

Anonymous traveler

An outdoor patio with a brick floor, a grill station, and a pergola structure.

Homewood Suites by Hilton Hagerstown

Hagerstown

10/10 Excellent

Anonymous traveler

A modern living room with a fireplace, wooden wall paneling, and a large clock.

Country Inn & Suites by Radisson, Hagerstown, MD

Hagerstown

10/10 Excellent

Steven

An indoor swimming pool with stone walls and large arched windows.

Holiday Inn Express & Suites Hagerstown by IHG

Hagerstown

10/10 Excellent

Macy

A spacious lobby with a modern design, featuring a seating area with patterned dividers, a flat-screen TV mounted on a brick wall, and a staircase leading to another level.

Holiday Inn Express Greencastle by IHG

Greencastle

10/10 Excellent

Anonymous traveler

A reception area with a wooden reception desk, a glass-top console table with a lamp, and a large ornate mirror on the wall.

Super 8 by Wyndham Hagerstown/Halfway Area

Hagerstown

10/10 Excellent

Jennifer

A spacious hotel lobby with a bar area, seating arrangements, and a large TV screen.

Comfort Suites Hagerstown Southeast

Hagerstown

10/10 Excellent

Ann

A rooftop terrace with outdoor seating, a fire pit, and a view of the sunset over a mountainous landscape.

SpringHill Suites by Marriott Frederick

Frederick

10/10 Excellent

Anonymous traveler

A hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a window with curtains.

Cobblestone Hotel & Suites - Waynesboro

Waynesboro

10/10 Excellent

Anonymous traveler

A two-story house with a dark roof, a visible chimney, and a well-lit entrance.

Antietam Overlook Farm

Keedysville

10/10 Excellent

Anonymous traveler

A Hampton Inn & Suites hotel with a modern facade, large columns, and a well-lit entrance.

Hampton Inn & Suites Frederick-Fort Detrick

Frederick

10/10 Excellent

Anonymous traveler

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 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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