
Apartment holiday rentals in Cumberland
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Top-rated apartment rentals in Cumberland
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Cumberland apartment rentals
Weekly apartment rentals

Lovely 1100 Sq. ft. 1 bedroom basement apartment
Between the beautiful look of the inside and out of this stay and the care shown by Marvin and Lisa it is overall a 5 star experience

NamaStay Playhouse
Patrick’s place was unique and interesting. Lots of space. Cool art.

Kat's Place
Awesome from start to finish. Can’t wait to come back.

Queen City Gem
Nice roomy apartment with direct access to the Cumberland Walking Mall - only steps from Cafe Mark. We thought the apartment was nicer in person that what the pictures showed.

Wishes Inn at 90 Goff St. #H
Christie was communicative and a fast replier! Would stay again!

Clatter House
Great host. Communication was awesome. Love the apartment and location. Central so you can walk to everything on the main street in Frostburg. Would stay again😃

Vintage-cool pad @VictorianManse
This is lovely gem of an apartment with all the amenities you need for a weekend getaway. the larger bed is a memory foam queen bed and there's another double bed. We loved the unique light fixtures and furniture and little touches that made us feel right at home. Love provided lots of local perspectives on where to go, places to eat, and happenings. Very quiet and peaceful in the apartment. location is great bc you can walk to town to eat or drink or get to the train station or bike path. lovely all around!
Private apartment rentals

Dwntwn Spot on Hambright's Alley! Walk Everywhere
One of the best hosts I’ve stayed with, and great apartment that met all my needs. Host was very responsive, with fast replies and great service. Going above and beyond when there was any issue. I was here for a long term stay and the apartment met all my needs! Great kitchen for cooking, nice living area for relaxing, and clean bedroom and bathroom. It’s also very conveniently located walking distance to downtown with many great restaurants / eateries of all varieties. The back porch is also a nice touch as it’s quite spacious. Would definitely recommend staying with this host!

The Downtown Flat at Creekside
The “Flat” above Creekside Provisions was amazing! Sam and Jeff were very outgoing and easy to talk with about any questions or suggestions. The flat is beautiful and cozy with great amenities. They provided us with great recommendations with places to easy and things to do!! Would love to return. They even opened their store beneath on a day they were closed so we could shop! Thanks again Sam and Jeff!!

Easy like a Sunday Morning 1 BR apt great location
Kim’s place is about as ideal as it gets. It’s located in a picturesque neighborhood a short walk away from the pedestrian mall. The surrounding area has all of the necessities anyone could need, also within walking distance. Restaurants (I fully endorse $6 slices of pizza the length of my forearm), Taprooms (Diving Creek is perfect), awesome little boutiques (Tin Top is a must stop), and plenty of historical locations to check out. The place itself is beautiful and perfect if staying in is more your speed. It had all the must haves for having a quiet day (or two) indoors. Kim’s communication was prompt and clear without fail. I’ll be looking to book with her again when I return to Winchester, without a doubt.

"Sweet Suite'
We loved the place, such an awesome little community, already planning our return.

Steeple View Flat in Historic District
Very cozy and quiet space. Loved the extras like aromatherapy pillow spray and popcorn. Nice selection of coffees, really nice shower and super comfy bed. I only stayed one night. Would love to return for a longer stay. Kathy was very responsive when I had an issue with finding the right door!

Cute & Cozy Apartment!
We loved this apartment!! The shed to store our bicycles was on the back side of the building and initially a little hard to find, but Rachel was extremely helpful in helping us locate it. The place was quiet, clean and very comfortable! Lots of nice places to eat and a great, small town atmosphere to enjoy an evening walk. We stayed here after cycling the GAP for 60 miles and got some much needed rest, relaxation, showers and food. Thanks so much Rachel!!!

Private Apt Near Cumberland, MD
We had no problem finding the apt. The apt was very clean & cozy. It was just what we needed for our weekend getaway!! Thanks for a great place to stay!!

Oldtown Schoolhouse. C&O Canal Lock 70.
The place is very spacious and clean. Lots of room for bikes and all your gear. Would stay again.
Apartment rentals with a hot tub

Azul Apt
Great place for a few days. We loved being able to walk to restaurants and the state park. The hosts were kind and responsive.

Host unit
Stopped in town on a road trip for the night. The room was just like the photos. I asked ahead for some extra pillows/blankets for my kids and their bed was made when I got there. The bubble tub was perfect after hours of driving. Everything was clean and comfortable. Perfect for a day trip, very close to restaurants and shops we were able to walk to everything which was nice after driving all day.

Oakland Home Efficiency Apartment
An absolutely beautiful location! I was able to watch the leaves change in fall while soaking in the deck hot tub. The studio apartment was perfect as my home away from home while on a travel nursing assignment. I had everything I needed. I was able to bring my roku and watch my TV shows while relaxing in the recliner chair. The shower is very roomy. I love that a washer and dryer was included. The only thing I wish it had was a toaster oven…but that is a luxury not a need. The stove, toaster, and microwave were perfect for my month stay. I highly recommend this place for anyone looking to “get away” or working in nearby by Oakland, MD. The host is wonderful and very responsive.

The Parlor Suite
Excellent stay in a nice part of town

Sweet 68
For my first time being there was really really nice. I love the small town. Never had to worry about anything. It was really nice. She was a very good host. I have nothing bad to say.

Downtown 1920's Gas Station with Hot Tub
Steve was extremely accommodating with booking and was fast to respond making booking his property seamless. GORGEOUS Property with lots of local restaurants and coffee shops nearby! The amount of detail that was put into the restoration of this property must be appreciated. Side note the Nespresso machine is something all Airbnb hosts should take notes on.. waking up to a watery Keurig coffee is no fun. Great job Steve and thank you again! Hope to stay at one of your properties again in the future.

Yoder School Guest House with wifi and hot tub
Rhoda’s place was wonderful! It was perfect for our needs over the weekend. Very cozy and clean. Rhoda was a wonderful host and thought of everything we needed. I would definitely recommend to anyone wanting to stay in the Grantsville area!
Quick stats about flat rentals in Cumberland
Total rentals
20 properties
Nightly prices starting at
£52 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Seven Springs Mountain Resort
- Whitetail Resort
- Fallingwater
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