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

Mountain Retreat-Stunning Views/Pool/Hot tub
We had an incredibly relaxing, peaceful, quiet getaway. The house is more than enough space for 2 people, well stocked kitchen, amazing scenery. Beautiful Mountain View’s, screened in porch, super serene.

October House
Overall very clean and well-maintained house with plenty of space. Host was also very thorough with instructions making check-in and check-out very smooth.

Stone Spring - Heated Salt Pool - on 2.5 Acres
Seth was a great host and we loved the place

Spacious Retreat with Outdoor Firepit & Large Deck
Anna's place is spacious and beautiful, as advertised. I booked it for a weekend with friends and everyone loved it. Anna was friendly and responsive. I would absolutely book it again if I'm back in the area.

Gayte House Gay Owned, Liberal Oasis
This was the perfect choice for a girls' weekend in Harper's Ferry. We loved the character of the historic home and the location was ideal for hiking, shopping, dining and relaxing. Would absolutely stay here again in the future.

Historic 1927 Home in Old Town Fredericksburg, VA
This home on Douglas St. is a fabulous place to stay. Three comfortable beds with lovely linens. Fully fenced in back yard for your furry friends. Well stocked kitchen with pots/pans etc. Large fridge. Perfect porch with a gate so we could let the pups be free when we were out there with them. The location is ideal. A few minutes walk to Williams St. and all the restaurants and shops. Caroline St is just a little farther ( easily walkable). The homes on Washington St are a must see. Very close to historic monuments and homes ( Kenmore house) , shopping, walking paths and everything good about FXBG. I would highly recommend Amy & Nicks place and i will definately be staying again.

More Luxury = Gym + Entertainment + Best Location
This was the perfect place for my group’s weekend getaway to charming Frederick. Despite the vibe being very cozy, the four of us still felt like we each had our respective space. We were also grateful for Joseph’s communication throughout as it made for a smooth experience during our trip. We’ll definitely be back!

Stylish & Cozy Getaway in Historic Culpeper
Was here for a short time but we are already looking to rebook in the next month or so! Super comfortable and peaceful!
Apartment rentals with outdoor seating

The Apartment at Dark Run Retreat
Jennifer’s place was amazing! A fully private guest house with tons of space and well stocked. Beautiful location and we were excited to use the hot tub. Would definitely stay again when visiting Shenandoah.

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!

Lena's Downtown Vintage Flat with Parking
Pamela's place was a wonderful older quirky home. The bed was comfortable and the place very homey. Hubby and I loved staying here. Very close/walkable to food, shopping and sites. The walk along Carroll Creek was beautiful. We highly recommend the Italian restaurant across the street. We absolutely loved our stay and Frederick.

Carroll Creek Private Apt./Luxury King Bed
The property is great, and located right in the heart of downtown Frederick. Terry was very responsive, and even offered me the chance to check on early since it had become an option. I would happily stay here again.

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.

Shenandoah Valley apartment with view
The apartment was lovely and the area was beautiful. We had a great time while we were visiting. Everything was just as expected from the description, the whole process was very easy. My family and I were very pleased. Thank you very much for a great vacation get away.

Spacious and bright 1 bedroom apartment near EMU
carrie's place is very inviting and clean, also peaceful, you will hear the dog occasionally but didn't bother us, bed is comfy , bathroom is big, loved the hot hair fan. it has everything we needed.

1 Bedroom Apartment in Downtown Berkeley Springs
Everything was perfect! The instructions were clear and Jason was very responsive. The location is perfect and in walking distance from many local restaurants and parks!
Condo rentals with outdoor seating

Historic Two Bedroom in Old Town Warrenton
Cozy, comfortable, everything you need and nothing you don't. The interior stone walls were especially lovely, as was the patio outside. Great place all around and very convenient to Main Street. William was a great host!

Quiet Apartment, Hot Tub, Downtown Frederick, Dogs
I absolutely loved this listing! The location was perfect and in the heart of downtown Frederick. We were walking distance or a short drive from restaurants and shops. The listing was clean, clutter free, and really nicely decorated. The hosts were very responsive and friendly. I would definitely recommend this listing, and would stay there again.

Massanutten Woodstone 2-BR, 2 Bath
Andy was very responsive and gave clear instructions. We had been at this resort a few times in the past and the unit we received was very nicely appointed and updated. We had all amenities and were super close to the indoor pool and gym. Comfortable.

The Room with the Views!
It was great! I didn’t realize just how close it is to the slopes. We just walked straight to the resort. The people at the resort were nice and the random people we met. It’s a great spot to stay.

Beautiful 2BR/1BA Renovated Condo near DC
Great little spot to get some rest! We enjoyed our stay and loved playing in the grass out back. Host was super proactive and allowed us to check in early for a small fee. Washer and dryer was nice to have and the master bathroom was large and perfect. Had a nice walk in closet with a door to the bathroom. Nice living room setup for the kids to play games on the table. Thank you for letting us enjoy your home. Would recommend!

Lark's Nest on Market
We very much enjoyed our stay and appreciated being able to bring our dog. It’s a great layout, well decorated, and the deck has a terrific view of the sunsets. Easy walking distance to the restaurants and Baker Park. We will be glad to return.

The Daisy in Historic Occoquan (Mins to DC)
I've stayed in a few different places in Occoquan, which I adore!! This one is by far my favorite for the location and it really is a great value!!

Mountain views, quiet & relaxing, pet friendly
We had such a lovely stay at this cute mountainside condo! The space was clean, cozy, and had everything we needed for a comfortable and relaxing trip. Doug’s recommendations for local food spots and hiking trails were so helpful!
Quick stats about vacation rentals with outdoor seating in Winchester
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Bryce Resort
- Luray Caverns
- Whitetail Resort
- Cacapon Resort State Park
- Stone Tower Winery
- Gambrill State Park
- Cunningham Falls State Park
- South Mountain State Park
- Robert Trent Jones Golf Club
- Twin Lakes Golf Course
- Shenandoah Valley Golf Club
- Notaviva Vineyards
- Whiskey Creek Golf Club
- Sly Fox Golf Club
- Berkeley Springs State Park
- JayDee's Family Fun Center
- Bowling Green Country Club
- Reston National Golf Course
- Creighton Farms
- River Creek Club
- Car and Carriage Caravan Museum
- Dinosaur Land
- Hidden Creek Country Club
- Herndon Centennial Golf Course