Vacation rentals in Hagerstown

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Top-rated vacation rentals in Hagerstown

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Guest favorite

Guest suite in Shepherdstown

4.96 out of 5 average rating, 564 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.

Oct 2 – 9

R1,681 ZAR per night

Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 251 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 21 – 28

R2,152 ZAR per night

Guest favorite

Home in Greencastle

4.97 out of 5 average rating, 192 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

Oct 31 – Nov 7

R2,213 ZAR per night

Guest favorite

Home in Inwood

4.89 out of 5 average rating, 544 reviews

Arden House, Inwood WV

Ground level studio apartment. No steps. Completely separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed and sofa. In a separate living area, there is a queen bed, TV, private bath, desk, table, microwave, convection oven, air fryer, refrigerator Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic.

Feb 4 – 11

R1,625 ZAR per night

Guest favorite

Guest suite in Smithsburg

4.99 out of 5 average rating, 151 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, dog-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 4 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Mar 8 – 15

R1,641 ZAR per night

Guest favorite

Guesthouse in Myersville

4.93 out of 5 average rating, 189 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.

May 18 – 25

R1,786 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.

Mar 18 – 25

R1,536 ZAR per night

Guest favorite

Place to stay in Hagerstown

4.95 out of 5 average rating, 363 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 13 – 20

R2,537 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

Jun 14 – 21

R2,687 ZAR per night

Guest favorite

Guest suite in Sharpsburg

4.93 out of 5 average rating, 175 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.

Jul 2 – 9

R2,159 ZAR per night

Guest favorite

Home in Blue Ridge Summit

5.0 out of 5 average rating, 448 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.

Sep 23 – 30

R2,581 ZAR per night

Guest favorite

Condo in Chambersburg

4.98 out of 5 average rating, 220 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.

Feb 12 – 19

R1,635 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

Apartment in Hagerstown

5.0 out of 5 average rating, 18 reviews

The Violet Femme Studio

Feb 2 – 9

R1,531 ZAR per night

Guest favorite

Home in Hagerstown

4.95 out of 5 average rating, 37 reviews

Cozy & relaxing private apartment

Aug 25 – Sep 1

R1,715 ZAR per night

Guest favorite

Home in Hagerstown

5.0 out of 5 average rating, 9 reviews

Hawks Nest Hagerstown

Jul 18 – 25

R1,831 ZAR per night

Guest favorite

Guest suite in Hagerstown

5.0 out of 5 average rating, 13 reviews

Clover Cove

Aug 26 – Sep 2

R1,528 ZAR per night

Guest favorite

Home in Hagerstown

4.91 out of 5 average rating, 100 reviews

Modern, one bedroom home in Hagerstown

Sep 12 – 19

R2,195 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 3 – 10

R2,131 ZAR per night

Guest favorite

Home in Martinsburg

4.86 out of 5 average rating, 56 reviews

Home Comforts, a separate apt of 1500 sqft.

Dec 10 – 17

R1,202 ZAR per night

Guest favorite

Guest suite in Hagerstown

4.97 out of 5 average rating, 35 reviews

Private Suite - Pool, King Bed, Kitchen, Driveway

Apr 25 – May 2

R2,195 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
R569 ZAR before taxes and fees

Frequently Asked Questions

Do house rentals in Hagerstown have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Hagerstown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Hagerstown have free parking?
Absolutely! We offer over 20 house rentals with free parking in Hagerstown. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Hagerstown?
Four-legged friends are welcome in Hagerstown. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Hagerstown?
Hagerstown has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Hagerstown?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 20 homes with free parking, over 20 homes with wifi, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.
Are there vacation rentals with a dedicated workspace in Hagerstown?
Yes! Work meets play with ease at over 30 vacation 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.

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

Apartment in Hagerstown

Home in Hagerstown

Home in Hagerstown

Guest suite in Hagerstown

Home in Hagerstown

Apartment in Hagerstown

Home in Martinsburg

Guest suite 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

Do house rentals in Hagerstown have a kitchen?

Do house rentals in Hagerstown have free parking?

Are there pet-friendly vacation rentals in Hagerstown?

Are there family-friendly vacation rentals in Hagerstown?

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

Do apartment rentals in Hagerstown have wifi?

Are there vacation rentals with a dedicated workspace in Hagerstown?

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

Destinations to explore