Western Maryland Vacation Rentals

Compare 86 vacation rentals. Enter your trip dates to get started.
USA > Maryland > Western Maryland

Make Western Maryland your next getaway—choose from 86 great vacation rentals

When adventure calls or you find yourself wishing for relaxation among the scenic beauty of the great outdoors, nothing compares to the peace and quiet you'll find in Western Maryland! Boasting natural beauty in the form of lakes, rivers, mountains, and forests, as well as every kind of sport you could hope for, the western region of Maryland is a little-known vacation destination that is sure to grab your heart the minute you set eyes on it.

Explore Western Maryland house rentals, cabins, townhouses, and more

housing_type_house.jpg

House rentals

View 43 House rentals
housing_type_cabin.jpg

Cabins

View 18 Cabins
housing_type_townhouse.jpg

Townhouses

View 12 Townhouses

Western Maryland vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Recreational Therapy
2 Bedroom | 1 Bath | Sleeps 5

Recreational Therapy - Oakland, MD

$132 avg / night
Luxury Lake
4 Bedroom | 5.5 Bath | Sleeps 12

Luxury Lake - Oakland, MD

$595 avg / night
Lakeview Loft
1 Bedroom | 1 Bath | Sleeps 4

Lakeview Loft - Oakland, MD

$112 avg / night
Swallow Falls Cabin #1
1 Bedroom | 1 Bath | Sleeps 4

Swallow Falls Cabin #1 - Oakland, MD

$108 avg / night
Incognito
3 Bedroom | 2 Bath | Sleeps 8

Incognito - Oakland, MD

$147 avg / night

View 81 more homes

Recent Western Maryland vacation rental reviews

This was a great house for our family of 6. There was plenty of room to spread out and enough space to hang and watch a movie together. The location was great, but be mindful that if not all of the slopes are open you may not be able to ski right out or in. That being said it was about a 50 yard walk to an open trail. We thoroughly enjoy d coming back and relaxing in the hot tub and some good quality family time. The property manager was fantastic! We got some weather on the day we were leaving and He was very accommodating to our requests. The listing does indicate that 4 wheel drive is recommended, but if there is any chance of weather I would say strongly suggested. It’s a steep windy climb up to the house. We would absolutely recommend Stella’s retreat and hope to go back again.
Sharon D. | Feb 2023
My family of 5 stayed here over the weekend to enjoy skiing at Wisp Resort. The house is only 5-10 minutes from Wisp but you feel like you are in the middle of a forest. It snowed while we were there and the kids had so much fun playing in the woods behind the house in the snow. The house was clean, had all the towels and linens we needed, and the kitchen was well stocked with things like paper towels, salt and pepper, filters for the coffee pot, hand soap and dishwasher soap. The beds were very comfy - 2 queens in the upstairs room and 1 queen downstairs next to the kitchen. We also really enjoyed all the games at the house like Monopoly, Uno, Mexican Train dominos, Jenga and cards. This was such a welcomed surprise and kept our 3 young kids entertained. Recommendations: If coming in the winter bring slippers and extra blankets to use while sitting in the living room. You also need 4 wheel drive to get in and out of the neighborhood. The roads weren't plowed in the neighborhood when we left at 8:30am to go skiing but we had no problems with our 4 wheel drive.
Jennifer M. | Jan 2023
Booked this house for my birthday get away. The house was great, clean, and accommodating to all parties. The wifi was sometimes spotty and water wasn’t always warm. The photos aren’t up to date, the TVs are actually way more up to date and kitchen is as well. I would definitely book again minus the small hiccups.
William H. | Jan 2023
Western Maryland vacation rental FAQ

Yes, 24 of our Western Maryland homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 81 of our Western Maryland vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Western Maryland vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Western Maryland team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Western Maryland, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning


Now you can experience the mountainous beauty of Western Maryland with one of our comfortable vacation rentals. The whole family will be wanting to come back for more.

Discover Western Maryland


The 10 Best Hiking Trails Near Deep Creek Lake

The Best Deep Creek Lake Cabins for Any Season