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, 254 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 8 – 15

$98 per night

Guest favorite

Home in Greencastle

4.97 out of 5 average rating, 197 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

Sep 29 – Oct 6

$102 per night

Guest favorite

Apartment in Clear Spring

4.99 out of 5 average rating, 364 reviews

Clean, quiet. Whitetail, I-70/I-81 15 min away!

Come, relax and enjoy your stay in the area with us! The perfect HideAway to hang your hat, let your hair down or to enjoy privacy, peace & quiet while you work online on your laptop. Ski day/evening during the winter or golf during suitable weather at Whitetail. Visit other attractions including National Parks to visit, hike or bike. Super restaurants just 5 min away! Off the beaten track, very clean & well kept. Behaved, furry friends invited! We have a back-up generator so no power outages!

Nov 6 – 13

$98 per night

Guest favorite

Guest suite in Smithsburg

4.99 out of 5 average rating, 156 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.

Jul 18 – 25

$75 per night

Guest favorite

Home in Myersville

4.97 out of 5 average rating, 149 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!

Sep 24 – Oct 1

$145 per night

Guest favorite

Guesthouse in Myersville

4.93 out of 5 average rating, 192 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

$84 per night

Guest favorite

Guest suite in Hagerstown

5.0 out of 5 average rating, 400 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 6 – 13

$71 per night

Guest favorite

Place to stay in Hagerstown

4.95 out of 5 average rating, 365 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.

Oct 19 – 26

$117 per night

Guest favorite

Guest suite in Sharpsburg

4.93 out of 5 average rating, 179 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. 7 mi to Rockland Estates venue.

Aug 6 – 13

$95 per night

Guest favorite

Home in Blue Ridge Summit

4.99 out of 5 average rating, 452 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 24 – Oct 1

$121 per night

Guest favorite

Condo in Chambersburg

4.98 out of 5 average rating, 232 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 18 – 25

$76 per night

Superhost

Loft in Martinsburg

4.9 out of 5 average rating, 113 reviews

The Penthouse-Cool Vibes

Imagine being downtown near the restaurants, bars, and shopping. Go up 2 flights of stairs and you've arrived in heaven. The breathtaking views from the top floor is memorable. You'll love the light that spreads out through the huge windows! Enjoy the huge king size bed or just hang out in the comfy living room. You are going to make your friends so jealous when they see your pictures!

Nov 8 – 15

$115 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

Cabin in Shepherdstown

4.95 out of 5 average rating, 423 reviews

The Log Cabin

Sep 15 – 22

$92 per night

Superhost

Condo in Hagerstown

4.82 out of 5 average rating, 266 reviews

Historic & Cozy ~ Near Antietam Battle & WhiteTail

Jul 30 – Aug 6

$137 per night

Guest favorite

Cottage in Martinsburg

4.98 out of 5 average rating, 356 reviews

Last Rodeo Cottage

Jun 15 – 22

$96 per night

Guest favorite

Home in Chambersburg

4.93 out of 5 average rating, 148 reviews

Cheerful 2-bedroom home in the Boro Chambersburg

Mar 20 – 27

$77 per night

Guest favorite

Guest suite in Mercersburg

4.94 out of 5 average rating, 409 reviews

The 1780 Cabin on Main

Nov 28 – Dec 5

$104 per night

Guest favorite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 569 reviews

Historic Scrabble, Shepherdstown

Sep 12 – 19

$74 per night

Guest favorite

Guest suite in Chambersburg

4.89 out of 5 average rating, 138 reviews

Cute Place Just Out Of Town With A Country Feel

Jul 18 – 25

$58 per night

Guest favorite

Cabin in Berkeley Springs

4.93 out of 5 average rating, 121 reviews

Foxy's Cabin

Jul 22 – 29

$118 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
$30 before taxes and fees

Frequently Asked Questions

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.
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 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.
How much does it cost to stay in house rentals in Hagerstown?
Experience the best of Hagerstown with our house rentals, starting at about $40 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 House Rentals in Hagerstown?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 20 homes with air conditioning, over 30 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.
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.
Do house rentals in Hagerstown have wifi?
Absolutely! We offer over 30 house rentals with wifi in Hagerstown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Hagerstown have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Hagerstown. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Hagerstown

Top-rated vacation rentals in Hagerstown

Vacation rentals for every style

Cabins

Houses

Hotels

Popular amenities for Hagerstown vacation rentals

Stay near Hagerstown's top sights

Other great vacation rentals in Hagerstown

Cabin in Shepherdstown

Condo in Hagerstown

Cottage in Martinsburg

Home in Chambersburg

Guest suite in Mercersburg

Guest suite in Shepherdstown

Guest suite in Chambersburg

Cabin in Berkeley Springs

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 vacation rentals with a dedicated workspace in Hagerstown?

What types of vacation rentals are available in Hagerstown?

Are there pet-friendly vacation rentals in Hagerstown?

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

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

Are there family-friendly vacation rentals in Hagerstown?

Do house rentals in Hagerstown have a kitchen?

Do house rentals in Hagerstown have free parking?

Do house rentals in Hagerstown have wifi?

Do house rentals in Hagerstown have air conditioning?

Destinations to explore