Western Maryland holiday rentals

We found 3,072 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Western Maryland

Showing deals for:1 Jan - 8 Jan

Exterior - Evening
Main Area Living Room
Main Area Living Room
Full Kitchen
Exceptional
(291 reviews)

Large Luxury Chalet - Hot Tub, Sauna & VIEWS

Berkeley Springs

8% off
AU$8,164
for 7 nights, 1 home
AU$1,166 per night
includes taxes & fees
Large Luxury Chalet - Hot Tub, Sauna & VIEWS
Wrap around windows and views of nature.
Kitchen has breakfast bars on both ends.
Screened wrap-around porch is built for relaxing, with six Adirondack chairs.
Wrap around windows and views of nature.
Exceptional
(81 reviews)

Luxurious country home. 120 acres. 5 Bedrooms. Basement game room. Fitness Rm.

Berkeley Springs

8% off
AU$5,031
for 7 nights, 1 home
AU$719 per night
includes taxes & fees
Luxurious country home. 120 acres. 5 Bedrooms. Basement game room. Fitness Rm.
Exterior
Private kitchen
Dining
Kitchen/ dining room
Exceptional
(10 reviews)

5 Bedroom Cottage in Deep Creek

Oakland

8% off
AU$5,786
for 7 nights, 1 cottage
AU$827 per night
includes taxes & fees
5 Bedroom Cottage in Deep Creek
Living area
Terrace/patio
Marina
Living area
Exceptional
(22 reviews)

Sunset View: Lakefront Pet-Friendly + Hot Tub + Dock

Swanton

7% off
AU$5,337
for 7 nights, 1 home
AU$762 per night
includes taxes & fees
Sunset View: Lakefront Pet-Friendly + Hot Tub + Dock
Living area
Interior
Living area
Exterior
Exceptional
(122 reviews)

Secluded, romantic cabin with hot tub on 12 acres of woodland.

Cumberland

8% off
AU$2,771
for 7 nights, 1 cabin
AU$396 per night
includes taxes & fees
Secluded, romantic cabin with hot tub on 12 acres of woodland.
Laundry Room
Interior
New 2nd kitchen in lower level
Dining
Exceptional
(21 reviews)

Rainbow Chalet, a River Front Home on Savage River near Deep Creek Lake

Swanton

8% off
AU$4,566
for 7 nights, 1 chalet
AU$652 per night
includes taxes & fees
Rainbow Chalet, a River Front Home on Savage River near Deep Creek Lake
Interior
Living area
Living area
Interior
Exceptional
(17 reviews)

Log Cabin with Hottub, EV charger, Game room

Great Cacapon

9% off
AU$5,435
for 7 nights, 1 cabin
AU$776 per night
includes taxes & fees
Log Cabin with Hottub, EV charger, Game room
A longer wooded view looking up at the deck.
Enjoy the Dove’s Nest fully stocked kitchen.  Just bring your food for preparing your gourmet meals!!!
Terrace/patio
Enjoy the beautiful floor-to-ceiling stone gas fireplace.
Exceptional
(176 reviews)

Spectacular couples retreat, private wooded location, dog friendly, Fiber WiFi

Berkeley Springs

8% off
AU$2,362
for 7 nights, 1 cabin
AU$337 per night
includes taxes & fees
Spectacular couples retreat, private wooded location, dog friendly, Fiber WiFi
View from front porch
Kitchen
Walkway from driveway to entry door
Sunroom
Exceptional
(49 reviews)

Firefly Hill - Renovated farmhouse with large backyard - sleeps 8

Jefferson

12% off
AU$3,183
for 7 nights, 1 room
AU$455 per night
includes taxes & fees
Firefly Hill - Renovated farmhouse with large backyard - sleeps 8
Interior
Private kitchen
Property grounds
Dining
Exceptional
(36 reviews)

Oldtown Guesthouse

Oldtown

12% off
AU$1,372
for 7 nights, 1 home
AU$196 per night
includes taxes & fees
Oldtown Guesthouse
Private kitchen
Living area
Dining
Exterior
Exceptional
(20 reviews)

One Last Taste of Summer Before the Cozy Sets In

Hagerstown

8% off
AU$2,379
for 7 nights, 1 home
AU$340 per night
includes taxes & fees
One Last Taste of Summer Before the Cozy Sets In
Dining
Terrace/patio
Living area
Living area
Exceptional
(28 reviews)

Log Cabin Retreat w/ Hot Tub, Game Room, Fire Pit

Swanton

8% off
AU$4,955
for 7 nights, 1 cabin
AU$708 per night
includes taxes & fees
Log Cabin Retreat w/ Hot Tub, Game Room, Fire Pit
Christmas 2023
Open L-shaped living and dining area provides  space for family gatherings.
Our kitchen is very well supplied!
BR 2
Exceptional
(5 reviews)

Welcome Home: Comfortable Home for Families, Pets, Remote Workers

Hagerstown

17% off
AU$2,925
for 7 nights, 1 home
AU$418 per night
includes taxes & fees
Welcome Home: Comfortable Home for Families, Pets, Remote Workers
Interior
Terrace/patio
Private kitchen
Living area
Exceptional
(82 reviews)

🍁BE Surrounded by Nature🌲RELAX it’s a 5 Star Luxury Cabin🍁Hot Tub🌲Close to town🍁

Berkeley Springs

8% off
AU$4,936
for 7 nights, 1 cabin
AU$705 per night
includes taxes & fees
🍁BE Surrounded by Nature🌲RELAX it’s a 5 Star Luxury Cabin🍁Hot Tub🌲Close to town🍁
Terrace/patio
Property grounds
Exterior
Terrace/patio
Exceptional
(331 reviews)

Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub

Berkeley Springs

12% off
AU$4,436
for 7 nights, 1 cabin
AU$634 per night
includes taxes & fees
Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub
Private kitchen
Interior
Terrace/patio
Dining
Exceptional
(27 reviews)

The Cowbell - 3-bedroom farmhouse in charming Berkeley Springs

Berkeley Springs

12% off
AU$3,104
for 7 nights, 1 home
AU$443 per night
includes taxes & fees
The Cowbell - 3-bedroom farmhouse in charming Berkeley Springs
Living area
Fire pit
Dining
Exterior
Exceptional
(9 reviews)

Escape from the City. House near Harpers Ferry

Knoxville

8% off
AU$2,272
for 7 nights, 1 cottage
AU$325 per night
includes taxes & fees
Escape from the City. House near Harpers Ferry
Dining
Property grounds
The River is typically this low in July - August. Depending on how much rain
Interior
Exceptional
(87 reviews)

Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion

Hedgesville

8% off
AU$2,326
for 7 nights, 1 cabin
AU$332 per night
includes taxes & fees
Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion
Living area
Living area
Living area
Private kitchen
Exceptional
(34 reviews)

Secluded cozy cabin with modern amenities/hot tub/pet friendly/wifi

Berkeley Springs

8% off
AU$2,715
for 7 nights, 1 cabin
AU$388 per night
includes taxes & fees
Secluded cozy cabin with modern amenities/hot tub/pet friendly/wifi
Interior
Property grounds
Exterior
Private kitchen
Exceptional
(51 reviews)

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cumberland

8% off
AU$1,333
for 7 nights, 1 home
AU$190 per night
includes taxes & fees
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Living Room 2: second gathering space with sofa, 65 inch TV, washer & dryer.
Living room: open-concept gathering space with decorative wood-burning stove.
Exterior: front of The Spy House with covered porch seating.
East Bedroom, 2nd Floor: queen bed, rocking chair, writing desk. Shares hall bathroom.
Exceptional
(175 reviews)

The Spy House, Historic 1880s Home, Harpers Ferry

Harpers Ferry

9% off
AU$3,090
for 7 nights, 1 home
AU$441 per night
includes taxes & fees
The Spy House, Historic 1880s Home, Harpers Ferry
Dining
Exterior
Living area
Exterior
Exceptional
(48 reviews)

Cabin in the woods, hot tub, pool table, fire pit, swing set

Oakland

8% off
AU$6,480
for 7 nights, 1 home
AU$926 per night
includes taxes & fees
Cabin in the woods, hot tub, pool table, fire pit, swing set
Interior
Property grounds
Private kitchen
Dining
Exceptional
(58 reviews)

Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit

Oakland

9% off
AU$6,163
for 7 nights, 1 cottage
AU$880 per night
includes taxes & fees
Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit
Private dock
Upper deck view
Front
Living room, overlook to game room
Exceptional
(127 reviews)

Level lakefront, family-friendly, hot tub, low fees, private dock

Oakland

8% off
AU$10,472
for 7 nights, 1 home
AU$1,496 per night
includes taxes & fees
Level lakefront, family-friendly, hot tub, low fees, private dock
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The historical area of Western Maryland awaits your stay

Enjoy the history and other features of Western Maryland. Travellers to this scenic city praise the hiking, shopping and restaurants. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Western Maryland

Are you hoping to discover attractions to see in the area? You'll be sure to enjoy Western Maryland for its hiking and cycling. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Western Maryland a fun place to get away to. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Woods Resort Mountain View Course (2.4 mi / 3.9 km)
  • The Woods Resort Stony Lick Course (3.2 mi / 5.2 km)
  • Colonial Springs Spa (6.1 mi / 9.9 km)
  • Berkeley Springs Antique Mall (7.4 mi / 11.9 km)
  • Coolfont Spa and Wellness Center (7.4 mi / 11.9 km)
  • Hagerstown Speedway (17.8 mi / 28.7 km)

Exploring the natural features in Western Maryland

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Western Maryland. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Berkeley Springs State Park (7.3 mi / 11.8 km)
  • Cacapon Resort State Park (9.3 mi / 14.9 km)
  • Green Ridge State Forest (18 mi / 29 km)
  • Breezewood Proving Grounds (24.8 mi / 40 km)
  • Crystal Grottoes Caverns (25.1 mi / 40.4 km)
  • Greenbrier State Park (27.8 mi / 44.8 km)

How to get to and around Western Maryland

The nearest airport is in Hagerstown, MD (HGR-Hagerstown Regional), located 24.7 mi (39.8 km) from the city centre.

If you prefer to travel by train, Martinsburg Station, Allegany College Bus Stop and Cumberland Station are the main stations in the area.

Frequently asked questions

What is the best area to stay in Western Maryland when booking a holiday home?
If you're visiting Western Maryland, McHenry is regarded as one of the most sought-after areas to book a holiday home. While here, keep busy by touring leading attractions like Wisp Resort and Funland.
What is the most popular type of holiday home accommodation in Western Maryland?
The most in-demand types of holiday homes in Western Maryland are houses. Want something different? Stayz has many options to match our guests' unique needs, so you'll see properties in all sizes, and for all budgets. The ideal fit is ready and waiting for you — discover yours today.
How much does it cost to rent a holiday home in Western Maryland?
A range of things can affect what you'll pay for a holiday home in Western Maryland, such as the time of year, length of stay and property type. But, all of our holiday homes have one thing in common — amazing value. Simply add your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Western Maryland?
When you travel and the style and size of the property will determine the cost of your beachside escape. Type in your Western Maryland travel dates to see all your options on Stayz. Can't live without a hot tub, or maybe a private pool? Use the filters to choose the features and amenities you want.
What are popular home amenities in Western Maryland?
When it comes to home amenities that guests prefer in Western Maryland, off-street parking options, a microwave oven and a fridge are the most popular. With Stayz holiday homes, you'll discover options to fit your style and taste, whether you're going on a holiday with friends, family or even pets.
Are there large group holiday homes in Western Maryland?
There are 834 holiday homes in Western Maryland that can host a group of 10 or more people. Whether you're organising a holiday with extended family or some kind of special event, there's enough space to get your loved ones together under one roof.
Can I find two-bedroom holiday homes in Western Maryland?
Select from 204 two-bedroom homes in Western Maryland. Settle the kids into the second room or maybe fill it with a couple of your besties. There's a comfy spot for whoever's fortunate enough to be coming along.
Are there holiday homes with WiFi in Western Maryland?
Whether you want to keep up with the latest headlines, write a few emails or surf your social networks, there are 833 holiday homes with WiFi in Western Maryland. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How old do you have to be to rent a holiday home in Western Maryland?
The minimum age is generally 16, 18 or 21. It can differ across properties on Stayz, so check the rules of your preferred Western Maryland holiday home before booking.
How long can I rent a holiday home in Western Maryland for?
The amount of time you can stay in a Western Maryland holiday home for is down to each property. Simply tap in your dates of travel to view options offering extended stays. They include all the things you need to make your extended trip more comfortable and convenient, like kitchens and backyards. Some Stayz holiday properties may also offer discounted weekly or monthly prices, so you can hang around longer for less.