
Holiday rentals with outdoor seating in Charles Town
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Top-rated rentals with outdoor seating in Charles Town
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
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Popular amenities for outdoor seating rentals in Charles Town
House rentals with outdoor seating

XL spa like tub Movie Room Best beds EVER Lux desi
The condo was wonderfully detailed, lots of thoughful touches, would gladly stay again

Whole House -Seven Elms Farm B&B
I had a wonderful stay at 7 Elms. I had to come to the area for a work event in Gainesville, and my team and I decided to stay at this AirBNB. It was so lovely. Such a cool restoration of an old farmhouse, and the property was serene and wonderful. We didn't have time to explore the area, as we were working so much and long hours. the only thing I can speak to is the grocery store - and it had everything. We saw a bunch of wild animals during morning coffee time, and that was really special. I don't think I've actually ever seen groundhogs in person, and there's a hysterical duo that run the show. The hosts were easy to communicate with.

Gayte House Gay Owned, Liberal Oasis
This house was adorable and is in a location that couldn't be beat! We enjoyed our stay - coffee and wine on the decks and easy walks around the sites and shops in the lower town. Beds were comfortable, kitchen was well-stocked and the views from everywhere were amazing! Easy 20-ish minute drive over to Loudon County wine country, if that's your destination. Check-in and check-out was great. Easy with flexible timing, which we greatly appreciated. Dean was VERY helpful, especially when it came to parking - we brought three cars and he made sure we had ample space, even when some of our drivers were unsure of the narrow roads. (Roads are hilly and corners are sharp in the mountains, if you are not used to that.) The house could use a good dust and sweep, but dishes and linens were clean and plentiful. Not a dealbreaker, unless you have allergies - but it is an old house, after all, so some of it is to be expected. We would gladly stay again!

The Old Schoolhouse at High Meadows Estate
Very peaceful, a place to get away and relax. Restful. Grounds are well cared for.

Arden House, Inwood WV
Thank you as always for your hospitality and responsiveness! This is our third stay! Highly recommend.

City Charmer minutes from Old Town
This house is adorable and in a great location. Crystal is so kind and responds very quickly. I loved all the inspirational signage and having coffee in one of the rocking chairs on the porch. It was our first time in Winchester and we will definitely come back and would love to stay here again.

Cheerful 1-BR Duplex w/ backyard in Harpers Ferry
They had everything that we needed! Cleanly! Great location! I’ll definitely be staying here again!

Cozy Cottage
Super cute and quiet cottage. All of Winchester is easily drivable but it’s out of the main city which is nice. Was in town for graduation and it made the whole event process much easier!!
Apartment rentals with outdoor seating

The Boundary House Apartment
We had an excellent stay on our journey along the C&O canal. The owners were very responsive and accommodating to our larger group. Everything was pristinely clean and the bathroom/shower was luxurious. Very happy with our stay and big thanks to the homeowners!

Cozy Getaway near Harper's Ferry, C&O & Potomac
Todd was very flexible with our needs and plans for the stay. It was most appreciated.

Downtown Modern Studio apartment | History & Dining steps away
Super grateful for Zeb! This cozy little studio was perfect for a weekend getaway for me and the missus. Parking was easy and made unloading luggage a breeze. The place had everything we needed for a comfortable stay, and the location couldn’t have been better … right in the heart of historic Shepherdstown. Highly recommend!

Trundle Private Suite Location Lily Garden BnB
Great stay! It was an awesome location and there was lots to do within walking distance. Also appreciated the food that was present for us on arrival. There was a small but very nice backyard where we were able to make a fire one night. Host was very informative and responsive. Would definitely stay again.

Carroll Creek Private Apt./Luxury King Bed
Terry and Jessi were great! Excellent with communication their place is exactly as described. We loved that it is so close to the canal and enjoyed going for walks exploring the area in the mornings and evenings when we were “home.”

Best location! The Pullman Apt @ historic 1799 Inn
The apartment was great for our stay and in an amazing location! Very easy to get to, and Bryan & Cathy were proactive with instructions and local recommendations to make the trip easy to plan.

Newly repurposed Historic Home in Winchester VA!
This cabin was exactly like the pictures and as described! We forgot that chickens are mentioned in the listing until we arrived and saw them, they were very cute. Kitchen is pretty stocked with whatever you need to have simple meals but there is no oven/stovetop so definitely plan ahead, but Trent provides some appliances like a toaster oven, waffle maker, and coffee maker. Overall we had a great stay!

A Great Getaway — Foxglove Retreat
Such a beautiful place, the yard is peaceful and pristine. VERY spacious apartment/ studio! Comfortable bed!. We had a great stay!
Apartment rentals with outdoor seating

Large Condo Above Abolitionist Ale Works #201
I loved the character and feel of our stay! Wonderful natural lighting and plenty of space. Although the music downstairs lasted a bit longer than expected, it did not diminish in any way the quality of our stay and I would happily stay here again!

2 Queen & 1 Twin Bed / Mountain & Museum Fun
Very quiet and clean place! Michael was very responsive and I loved the museum room!

Modern Condo In Downtown Frederick
Spacious “condo” really the entire lower floor of a restored older home Fantastic location - easy walk to the restaurants and shops in the historic district

Ski🎿 & hike from front steps—Mountainside getaway
I think this is the best slope side ski condo at Whitetail. The slopes are right outside the door and the place is cute, clean, and comfortable. We will be going back!

Quiet Stay + Huge Apt + Hot Tub + Dogs, Walkable
Large place, great jumping off point and close to town for my partner, my dog and myself. Very clean, and set up great to watch TV at night or work from home. And a fully operational kitchen so you don't have to eat out every night. Thank you again!

Stay-in-Style Downtown Frederick
The place was so cozy and in a perfect location for visiting Frederick. We could walk to coffee, dinner, and downtown. Great stay! Christen was very responsive. My friend and I will be back next year!

Newly Renovated HUGE condo in heart of downtown!
This was a great spot! Definitely will stay again the next time we are in town. The location is amazing!!!

The Cozy Villa
Immaculate!! This is the cleanest AirBnB I've stayed in. Fully stocked with extra linens and pillows, snacks (what?!), every utensil and kitchen item you'll need, too many pluses to list. The back yard looks like a private forest, the house is so quiet and cozy, and close to gas stations, grocery stores, restaurants, etc. You'll love staying here :)
Quick stats about holiday rentals with outdoor seating in Charles Town
Total rentals
20 properties
Nightly prices starting at
$77 SGD before taxes and fees
Total number of reviews
830 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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- Georgetown University
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