Hagerstown Holiday Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Hagerstown

Newly renovated studio in Hagerstown--Self Check-in
Fridge, microwave, oven, stovetop

Newly renovated studio in Hagerstown--Self Check-in

10.0 out of 10, Exceptional, (25)
"Cute place. Property manager very responsive to needs. Great stay."
Newly renovated studio in Hagerstown--Self Check-in
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Fridge, microwave, oven, stovetop

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

10.0 out of 10, Exceptional, (5)
"Lovely property in Hagerstown. We stayed here with my 82 year old father while visiting family. Perfect accommodations! Very clean & comfortable. We had a little hiccup with our code to check in, but once Michelle saw our note, we got it fixed right away. Convenient to Main Street shops & food. We would definitely stay here again on our next trip!"
The price is AU$251
includes taxes & fees
1 Dec - 2 Dec
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Exquisite Hagerstown Home with Deck & Gazebo!
Property grounds

Exquisite Hagerstown Home with Deck & Gazebo!

10.0 out of 10, Exceptional, (4)
"This property was fantastic and had all the amenities we were looking for in a long weekend away. "
Exquisite Hagerstown Home with Deck & Gazebo!
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Smart TV, fireplace

New Hagerstown Apartment - Self Check-in. Sleeps 4+

9.6 out of 10, Exceptional, (13)
"it was closed to my fathers house, only complaint i had was that the app or website wouldnt let me message the host. kept saying didnt go thru and prompted me to retry which i did 3 times with same resuts "
The price is AU$210
includes taxes & fees
3 Dec - 4 Dec
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Exquisite Hagerstown Home With Deck & Gazebo!
Property grounds

Exquisite Hagerstown Home With Deck & Gazebo!

3.0 star property
Exquisite Hagerstown Home With Deck & Gazebo!
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
TV

Updated condo in the heart of Historic District with patio, streaming, fast WiFi

10.0 out of 10, Exceptional, (9)
"Loved everything from the location to the decor! Perfect ladies spa/refresh weekend!"
The price is AU$493
includes taxes & fees
2 Dec - 3 Dec
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
Cozy, Fully Renovated, 1 Bedroom Home in Connersville
Fridge, microwave, oven, stovetop

Cozy, Fully Renovated, 1 Bedroom Home in Connersville

Cozy, Fully Renovated, 1 Bedroom Home in Connersville
5 min walk to BSU Campus - Quiet Neighborhood
Property grounds

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (53)
"A group of us were in town for Ball State Hoco. The house location was conveniently located near campus and tailgating. Plenty of room for us all. House was clean and comfy. It did have a musty odor to it when first entering. That would be the only draw back. "
5 min walk to BSU Campus - Quiet Neighborhood
country home with hot tub close to town
Fridge, microwave, oven, stovetop

country home with hot tub close to town

9.0 out of 10, Wonderful, (32)
"Property is very clean. I was alone but more than enough room for a family. I had trouble checking in because I could not get the lock info from the VBRO communications, and I could not reach the landlord. it took over an hour on the phone with VBRO to get the appropriate info. The house itself is very nice. Small fenced yard for my dog was a plus"
country home with hot tub close to town
Cardinal Cottage - 2 bedroom cozy home
Exterior

Cardinal Cottage - 2 bedroom cozy home

9.2 out of 10, Wonderful, (7)
"My wife and I enjoyed staying at this house. It was just what we needed for the night! It was clean, cozy and comfortable. We’d stay here again."
The price is AU$278
includes taxes & fees
14 Dec - 15 Dec
Cardinal Cottage - 2 bedroom cozy home
Entire Home with Modern Conveniences - New Castle
Fridge, microwave, oven, stovetop

Entire Home with Modern Conveniences - New Castle

10.0 out of 10, Exceptional, (6)
"We had to make a last minute trip to New Castle for our Fathers funeral. The house met all our needs. It was very easy to access and contact with owner quick and easy. Super convenient to multiple restaurants, Walmart, and downtown New Castle. "
The price is AU$322
includes taxes & fees
1 Dec - 2 Dec
Entire Home with Modern Conveniences - New Castle
Cozy Cabin with fireplace, hot tub & hiking trails
Outdoor pool, a heated pool

Cozy Cabin with fireplace, hot tub & hiking trails

7.4 out of 10, Good, (3)
"The property is amazing. Pictures do not do the gardens justice. The visiting horse and friendly cats were a plus. The pool is cloudy and needs more frequent cleaning than the weekly service due to its location under trees. The outdoor furniture also needs cleaning as do the dishes in the house. But you will hardly notice because the gardens are so well maintained and the hot tub works amazing."
Cozy Cabin with fireplace, hot tub & hiking trails
Westcott Mansion with Pickleball Court & Huge Gazebo
8 bedrooms, WiFi, bed sheets

Westcott Mansion with Pickleball Court & Huge Gazebo

10.0 out of 10, Exceptional, (25)
"This rental met all my expectations. We were a group of 14 ladies and the space was more than enough. Great kitchen supplies, very comfortable outside and parking. The communication was timely and informative. Thanks Richmond for a great weekend."
The price is AU$517
includes taxes & fees
2 Dec - 3 Dec
Westcott Mansion with Pickleball Court & Huge Gazebo
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
Smart TV, fireplace, DVD player

Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir

9.6 out of 10, Exceptional, (13)
"Nice cabin... Had some water/well issues that were a challenge yet the owner took care of it. Would stay here again."
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
Downtown New Castle Indiana Condo Available for short-term and long-term stays.
Smart TV

Downtown New Castle Indiana Condo Available for short-term and long-term stays.

10.0 out of 10, Exceptional, (18)
"loved our stay"
Downtown New Castle Indiana Condo Available for short-term and long-term stays.
Boho Bungalow off Main-one block from Lovely Park
Interior

Boho Bungalow off Main-one block from Lovely Park

9.4 out of 10, Exceptional, (6)
"My husband, son, and I stayed here the weekend of our daughter’s graduation from Miami University. It was so cute and easy to access. The communication was awesome and check in/check out process was simple. Would definitely recommend."
Boho Bungalow off Main-one block from Lovely Park
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Exterior

Quaker Hill Cottage on gated estate with fire pit & hiking trails

9.6 out of 10, Exceptional, (19)
"Thank you so much for such a lovely home to be our home base as we returned to Richmond from all over the country to celebrate our 30th reunion at Earlham College! We loved the space, the decor and the communications with our host. "
The price is AU$344
includes taxes & fees
1 Dec - 2 Dec
Quaker Hill Cottage on gated estate with fire pit & hiking trails
The Hidden Gem in downtown Connersville
Game room

The Hidden Gem in downtown Connersville

9.8 out of 10, Exceptional, (14)
"I originally booked this as a place to stay after we went to the Taylor Swift concert in Indianapolis. It’s about a 15-minute drive off the freeway and I passed through a couple of small towns to get to our destination. One would never guess that this lies hidden within this building. We thoroughly enjoyed it and have talked about a girls’ trip here in the future. I would stay here again."
The price is AU$1,194
includes taxes & fees
1 Dec - 2 Dec
The Hidden Gem in downtown Connersville
Charming Home! Prime Location! Dog-Friendly!
Terrace/patio

Charming Home! Prime Location! Dog-Friendly!

9.6 out of 10, Exceptional, (5)
"We thoroughly enjoyed our stay. Mara was very communicative and the house was very cozy and charming. It was a delight to walk around the neighborhood and see all the beautiful historic homes. Our group of 5 adults had a great stay and we were able to bring our dog, which was great!"
The price is AU$545
includes taxes & fees
30 Nov - 1 Dec
Charming Home! Prime Location! Dog-Friendly!
La Dolce Vita
Private kitchen

La Dolce Vita

2.0 out of 10, (2)
"The pictures uploaded are either very old, or doctored. Bed sheets had stains on them with black light. Cameras installed throughout the inside of the home. No running water when we arrived. We checked into a motel, and then owner tried to charge me $2000.00 for "water damage", when there was no running water and we never stayed."
The price is AU$397
includes taxes & fees
30 Nov - 1 Dec
La Dolce Vita
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.
Don't see what you're looking for?
See all available properties in Hagerstown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Hagerstown you may be interested in

Newly renovated studio in Hagerstown--Self Check-in
Fridge, microwave, oven, stovetop

Newly renovated studio in Hagerstown--Self Check-in

10.0 out of 10, Exceptional, (25)
"Cute place. Property manager very responsive to needs. Great stay."
Newly renovated studio in Hagerstown--Self Check-in
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Smart TV, fireplace

New Hagerstown Apartment - Self Check-in. Sleeps 4+

9.6 out of 10, Exceptional, (13)
"it was closed to my fathers house, only complaint i had was that the app or website wouldnt let me message the host. kept saying didnt go thru and prompted me to retry which i did 3 times with same resuts "
The price is AU$210
includes taxes & fees
3 Dec - 4 Dec
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Fridge, microwave, oven, stovetop

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

10.0 out of 10, Exceptional, (5)
"Lovely property in Hagerstown. We stayed here with my 82 year old father while visiting family. Perfect accommodations! Very clean & comfortable. We had a little hiccup with our code to check in, but once Michelle saw our note, we got it fixed right away. Convenient to Main Street shops & food. We would definitely stay here again on our next trip!"
The price is AU$251
includes taxes & fees
1 Dec - 2 Dec
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

Are there holiday rentals in Hagerstown?

Yes, there are holiday rentals in Hagerstown close to Abbott's Candy Shop, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Hagerstown has to offer?

5 min walk to BSU Campus - Quiet Neighborhood: This holiday home rental outside of Hagerstown offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Hagerstown?

Family-friendly attractions include Abbott's Candy Shop, whereas Scout Lake is a spot to enjoy the outdoors. In the wider area, you’ll find Warm Glow Candle Company and Summit Lake State Park.

What’s a holiday rental in Hagerstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hagerstown. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip.