
Holiday rentals with outdoor seating in Cumberland
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Top-rated Holiday Houses with Outdoor Seating in Cumberland
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Popular amenities for Cumberland outdoor seating rentals
Holiday House Rentals with Outdoor Seating

The Little Red Schoolhouse
SUCH a cute place! Super clean inside and out! The hot tub was perfect and ready to go when I got there. It's also an easy commute to Winchester and farmers markets. Perfect for a girls night or a couples get away.

Access to Yough Lake, Ski Resorts and Hot Tub!
From booking to checkout, everything about our stay was perfect!! I made changes to our arrangements shortly after booking and David was quick to respond and very helpful. Upon arrival, easy entry into the house, and everything was very clean and just as pictured. This location is exactly what we hoped for our weekend!! Peaceful, quiet, clean, and relaxing! I would highly recommend this location and look forward to renting here again. I can't thank you enough for helping to our New Year's weekend getaway so memorable!!

Johnson Heights Getaway
This is our second time staying at the house. The house is very welcoming and homey. Very clean! Plenty of necessities. She always has extra blankets and plenty of essentials. Extra parking on street if needed. Close proximity to downtown Cumberland. Safe neighborhood. Will stay again!

Allegany Retreat
Thank you for a great last minute accommodation! The home fit perfectly for our needs.

Come play in the country! Private River estuary!
We very much enjoyed our stay. The house and property are well maintained and everything functioned the way they should. The property offered a relaxing environment, which is what were looking for. Cynthia's place is dog friendly, which made our stay even better. Downtown is only a 10 minute ride. All in all, we had a great time and would recommend Cynthia's place to anyone who is seeking a quiet getaway in well kept home.

Roundhouse Retreat near Bedford Springs Resort
We had a great time there it was so easy with her help. She was so responsive and helpful and the place was perfect looked exactly like the pictures. Recommend it to anyone looking to stay in Bedford!

Landmark One Lakefront with Dock Slip & Hot Tub
Stacy was such an accommodating host!! She was extremely easy to communicate with and very responsive! The house was very clean and cozy! The hot tub was also extremely clean!! Would absolutely book this house again!

Cozy Cottage
My friend and I absolutely loved staying at Matt and Sarah’s for the weekend! We had a great time exploring and felt very comfortable at the house when we were done for the day. Beautiful little home with all you could need, and they were so friendly!
Apartment rentals with outdoor seating

New! The Nest near Deep Creek
This place was excellent a great find. Diane was pleasant she greeted us with a smile and knew me by name. We arrived early and wasn’t a problem. To add to everything she left us some fresh eggs in the refrigerator. One of the cleanest places I ever stay in. Thank you Diane continue to the person God designed you to be and I will definitely be back.

Riverview Suite
Wandas place was great and nice and clean This location is only a short drive to deep creek and surrounding areas. it is very walkable and my dogs enjoyed the nearby trail. Wanda allowed my 2 dogs and was very responsive and let is check in a tad earlier. Wanda put a lot of time into the cute and welcoming decor in the apartment and it was very clean. Thanks for a great stay.

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!!

Rustic Ranch Guest Apartment
Great spot, very cozy and large! Accurate description and representative photos. I’ll be back next time I’m in the area!

Ord St Inn Unit Two, spacious 2nd floor apartment
Absolutely 100% Top notch! Immaculately clean, quiet, comfortable and Joe is a great host. I can't say enough about how perfectly this was setup.

Sierra Farmstead - Guest House
This is my fiance and I's second time staying at the farmstead, and we absolutely love it. We were so excited when it was available to book this weekend!! I can't say enough great things about it: it's always clean, tidy, well stocked with amenities, extremely peaceful, and the beds are so comfortable!! I truly can't recommend it enough!! 100/10.

"Home Sweet Home Suite" Come Sit on Our Porch!
Very convenient to the GAP for biking. We had a couple of minor issues, but these were addressed quickly. The beds were comfortable.

Charming 1-bdrm with balcony, Close to Everything.
One of the best hosts I’ve dealt with. She is quick with responding with any questions you may have and gives you plenty of recommendations around the area. She asks you how the stay is throughout the dates you are there. Overall a great host and the property is beautiful.
Condo rentals with outdoor seating

Top of The Slopes- 4 bdrm, Ski in/Ski out, Hot Tub
It was great and easy, they communicated very quickly and the location was great

Lake Access/2BR/2Bath/kitchen/pool/5m to Wisp
I wish there was an extra star for the Host! Lorena was super helpful, always responded less than 30 minutes, and made us feel welcome into her home. Personal touches say a lot, and she had written us a nice thank you card that was on the table when we arrived. It was also nice that we did not have to run out and get toiletries immediately as they were readily available upon our arrival. Lorena was also upfront with an issue involving the oven, however there was a toaster oven readily available if we so choose. I highly recommend her condo to anyone with a small group of people/small family that plans on staying in the Deep Creek area!

Private apartment in residential Cumberland, MD
Perfect accommodations! A very welcoming and attentive host who went above and beyond welcoming and providing anything and everything to make this stay extremely comfortable . The suite is curated beautifully and I felt very relaxed there. Love the woodwork and the quilt. Thank you Valerie. All went well for my friend 😊

Romantic condo with a view in historic Cumberland
We found the space on Race to be just what we needed for the motivation to get up and go to our daily bluegrass festival at the fairgrounds. If you needed something last minute, the Dollar Tree was a quick walk down the hill. The kitchen was perfect for morning coffee and eating routines. The couches were comfortable and the WiFi worked fine. All in all, this was a good location to suit our needs.

Turkeyfoot Sunset Apartment
Great place in a cool little town. Her place was nicely furnished and decorated. It was imma I late. The sprawling layout of the multiple units made would make it easy to have as much privacy as you want while providing an opportunity to engage with others if you chose to do so. We enjoyed playing on the lawn by the levee on the river. Her yard is at the confluence of two rivers. Diana was an outstanding host - very cheerful and helpful in guiding us to destinations.

Enchanting Condo in Nudist Mountain Community
Beautiful place, thanks Michele and Sean

Landlocked @ DCL Lakefront, Dock, Pool, Pickleball
I can't say enough great things about this place! it was so cozy and comfortable! My friend and I went for a girls getaway weekend to relax and this was so ideal! They even prepped the fireplace for us! I would definitely come back here and wouldn't even think of going anywhere else!

Cozy & spacious suite w/ loft. Lake Resort Lodge
Great stay! Clean. Other amenities in the complex. Lakefront complex with ample parking and inviting common areas and beautiful outdoor areas. Would stay again!
Quick stats about holiday rentals with outdoor seating in Cumberland
Total rentals
20 properties
Nightly prices starting at
$92 AUD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
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- Seven Springs Mountain Resort
- Whitetail Resort
- Fallingwater
- Hidden Valley Resort
- Cacapon Resort State Park
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- Wisp Resort
- Blue Knob All Seasons Resort
- Lodestone Golf Course
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