Vacation rentals in Hagerstown

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Top-rated vacation rentals in Hagerstown

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Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 253 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Amazing place to unwind, de-stress & get away. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting.

Mar 28 – Apr 4

R2,166 ZAR per night

Guest favorite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 567 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Aug 24 – 31

R1,611 ZAR per night

Guest favorite

Home in Greencastle

4.97 out of 5 average rating, 194 reviews

Country 2-Bed/2-Bath Apartment with Beautiful View

Rural agricultural setting but convenient to towns, golfing, Whitetail Ski Resort and civil war historical sites. Two bedrooms with queen beds w/linens, two full baths, full kitchen living room area, desk and outdoor firepit and chairs (firewood for additional fee). Queen pull-out sofa bed. Wi-Fi and HDTV. Paved drive/parking area. Pets welcome w/agreement. Short drive to I-81 and I-70 20 mins to Hagerstown 15 mins to Chambersburg 20 mins to Whitetail Ski Resort 1.5 hrs to Baltimore/Washington

Mar 7 – 14

R2,228 ZAR per night

Guest favorite

Guesthouse in Myersville

4.93 out of 5 average rating, 190 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

Jul 12 – 19

R1,756 ZAR per night

Guest favorite

Home in Myersville

4.97 out of 5 average rating, 147 reviews

The Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

Oct 9 – 16

R3,201 ZAR per night

Guest favorite

Guest suite in Hagerstown

4.99 out of 5 average rating, 397 reviews

Oak Hill Private Suite Historic North End

A recently renovated private suite in historic home only 1.5 miles from town center. Welcoming ‘walking’ neighborhood of architecturally diverse homes inspired by the Garden City Movement of early 20th C. Near both Interstate 81 and 70, Museum of Fine Arts, Whitetail Ski Resort, Antietam, Gettysburg, Frederick, C&O bike trail, wineries and outlets. Guests have enjoyed stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

Nov 9 – 16

R1,563 ZAR per night

Guest favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 643 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota guesthouse is the perfect get away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Feb 25 – Mar 4

R1,787 ZAR per night

Guest favorite

Place to stay in Hagerstown

4.95 out of 5 average rating, 364 reviews

Springhouse 1803 - easy I-70/81 access

If you are looking for a unique place to stay, come visit us at Springhouse 1803. Yes, there really is a spring under the house. After sitting empty for 20+ years, the house has been restored to be lived in again and it has maintained much of its colonial charm. The house has all the amenities you need for a comfortable stay. NOT A PARTY HOUSE, OWNER IS ON SITE. If you're looking for a day that is blocked, you can inquiry if its available, see below for more details.

Sep 15 – 22

R2,554 ZAR per night

Superhost

Condo in Hagerstown

4.82 out of 5 average rating, 266 reviews

Historic & Cozy ~ Near Antietam Battle & WhiteTail

★ TOP-THIRD FLOOR CONDO IN A HISTORY BUILDING – NO ELEVATOR ★ Retreat to the gorgeous 2BR 1Bath top-floor condo in the beautiful turn-of-the-century home in the heart of historic Hagerstown. It offers a relaxing retreat a few steps from the vibrant downtown and close to Antietam Battlefield, Whitetail Resort, and many more landmarks. ✔ 2 Comfortable Bedrooms ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Free Parking

Jul 14 – 21

R2,643 ZAR per night

Guest favorite

Guest suite in Sharpsburg

4.93 out of 5 average rating, 177 reviews

Guest Apartment by C & O Canal and Battlefield

Affordable Luxury! 1200 square feet Bright & modern newly remodeled basement apartment with private entrance. Fully equipped kitchen, 2 BR, 1 BA. It’s on the ground floor of a newly renovated home. Hostess and boyfriend, Charles, live on top, main floor. Shepherdstown, WV 7 mi. C & O canal 1/3 mi. Antietam Battlefield 1/2 mi. Sharpsburg 2mi. Harpers Ferry 25 min. Hagerstown 10 min.Many cool breweries & wineries within 15 min.

Sep 25 – Oct 2

R2,022 ZAR per night

Guest favorite

Home in Blue Ridge Summit

5.0 out of 5 average rating, 450 reviews

Colonial Era Spring House

A unique and private mountain top colonial era spring house, with two springs flowing thru the basement. Originally the site of a tannery in the 1700s. Here you can relax, recharge, and rejuvenate. We celebrate all four seasons where you can enjoy Mother Nature's ever changing scenery at 1300' above sea level with fresh mountain air. Our area offers many things to do, or you may choose to stay in and do nothing at all.

Oct 3 – 10

R2,643 ZAR per night

Guest favorite

Condo in Chambersburg

4.98 out of 5 average rating, 224 reviews

One-bedroom apartment with separate entrance.

Adorable one-bedroom apartment with separate entrance. Located 10 minutes from downtown Chambersburg. Whether its historical sight-seeing, culturally diverse restaurants, or local craft beer, there is plenty to see and do in this area. Built in 2021, this apartment is on the lower level of our custom built home. It also has a fully equipped gym. Pet friendly, No smoking, No parties.

Nov 6 – 13

R1,666 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Hagerstown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Hagerstown's top sights

Hagerstown Premium Outlets44 locals recommend

Valley Mall18 locals recommend

Walmart Supercenter6 locals recommend

Hagerstown City Park16 locals recommend

Sky Zone Trampoline Park7 locals recommend

Hagerstown Family Diner4 locals recommend

Other great vacation rentals in Hagerstown

Guest favorite

Guesthouse in Gettysburg

4.99 out of 5 average rating, 373 reviews

The Cock and Feather Guesthouse

Jul 19 – 26

R1,963 ZAR per night

Guest favorite

Home in Inwood

4.89 out of 5 average rating, 547 reviews

Arden House, Inwood WV

Dec 10 – 17

R1,635 ZAR per night

Guest favorite

Home in Hagerstown

5.0 out of 5 average rating, 10 reviews

Hawks Nest Hagerstown

Nov 4 – 11

R1,803 ZAR per night

Guest favorite

Home in Hagerstown

4.95 out of 5 average rating, 38 reviews

Cozy & relaxing private apartment

Jul 2 – 9

R1,727 ZAR per night

Guest favorite

Apartment in Hagerstown

5.0 out of 5 average rating, 19 reviews

The Violet Femme Studio

Jul 27 – Aug 3

R1,534 ZAR per night

Guest favorite

Guest suite in Hagerstown

5.0 out of 5 average rating, 15 reviews

Clover Cove

Sep 2 – 9

R1,550 ZAR per night

Guest favorite

Apartment in Hagerstown

5.0 out of 5 average rating, 57 reviews

Private, relaxing, quiet, 2 bdrm unit, Sleeps 4-6

Oct 10 – 17

R2,145 ZAR per night

Guest favorite

Home in Hagerstown

4.91 out of 5 average rating, 102 reviews

Modern, one bedroom home in Hagerstown

Dec 8 – 15

R2,210 ZAR per night

Show all

Quick stats about vacation rentals in Hagerstown

Total rentals
70 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
2.8K reviews
Nightly prices starting at
R573 ZAR before taxes and fees

Frequently Asked Questions

Are there apartment rentals with a dedicated workspace in Hagerstown?
Yes! Work meets play with ease at over 10 apartment rentals in Hagerstown featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Hagerstown?
Experience the best of Hagerstown with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Apartment Rentals in Hagerstown?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with a kitchen, over 10 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Hagerstown have a kitchen?
Absolutely! We offer over 20 apartment rentals with a kitchen in Hagerstown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Hagerstown have free parking?
Absolutely! We offer over 20 apartment rentals with free parking in Hagerstown. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly apartment rentals in Hagerstown?
Four-legged friends are welcome in Hagerstown. Choose from more than 10 apartment rentals for guests traveling with pets.
Do apartment rentals in Hagerstown have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Hagerstown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Hagerstown have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Hagerstown. Enjoy a tailored experience with all the comforts you desire.
What types of vacation rentals are available in Hagerstown?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Hagerstown. From over 20 apartment rentals to over 30 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there family-friendly house rentals in Hagerstown?
Hagerstown has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Hagerstown

Top-rated vacation rentals in Hagerstown

Vacation rentals for every style

Apartments

Cabins

Houses

Popular amenities for Hagerstown vacation rentals

Stay near Hagerstown's top sights

Other great vacation rentals in Hagerstown

Guesthouse in Gettysburg

Home in Inwood

Home in Hagerstown

Home in Hagerstown

Apartment in Hagerstown

Guest suite in Hagerstown

Apartment in Hagerstown

Home in Hagerstown

Quick stats about vacation rentals in Hagerstown

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there apartment rentals with a dedicated workspace in Hagerstown?

How much does it cost to stay in apartment rentals in Hagerstown?

What are the most popular amenities for Apartment Rentals in Hagerstown?

Do apartment rentals in Hagerstown have a kitchen?

Do apartment rentals in Hagerstown have free parking?

Are there pet-friendly apartment rentals in Hagerstown?

Do apartment rentals in Hagerstown have wifi?

Do apartment rentals in Hagerstown have air conditioning?

What types of vacation rentals are available in Hagerstown?

Are there family-friendly house rentals in Hagerstown?

Destinations to explore