Vacation rentals with outdoor seating in Winchester

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Popular amenities for Winchester outdoor seating rentals

House rentals with outdoor seating

Top guest favorite
Home in Lost City
5 out of 5 average rating, 132 reviews

Mountain Retreat-Stunning Views/Pool/Hot tub

YaelRating, 5 stars1 month ago
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.
Guest favorite
Home in Basye
4.85 out of 5 average rating, 40 reviews

October House

EmmaRating, 5 stars2 weeks ago
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.
Superhost
Home in Town of Rockingham
4.78 out of 5 average rating, 260 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

JohnRating, 5 stars2 months ago
Seth was a great host and we loved the place
Top guest favorite
Home in Banco
4.99 out of 5 average rating, 135 reviews

Spacious Retreat with Outdoor Firepit & Large Deck

BenRating, 5 stars2 months ago
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.
Top guest favorite
Home in Harpers Ferry
4.94 out of 5 average rating, 394 reviews

Gayte House Gay Owned, Liberal Oasis

EmilyRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Fredericksburg
4.99 out of 5 average rating, 201 reviews

Historic 1927 Home in Old Town Fredericksburg, VA

KarenRating, 5 stars3 days ago
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.
Guest favorite
Home in Frederick
4.94 out of 5 average rating, 157 reviews

More Luxury = Gym + Entertainment + Best Location

RachelRating, 5 stars4 days ago
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!
Top guest favorite
Home in Culpeper
5 out of 5 average rating, 81 reviews

Stylish & Cozy Getaway in Historic Culpeper

GloriaRating, 5 stars2 weeks ago
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

Top guest favorite
Apartment in Madison
4.96 out of 5 average rating, 218 reviews

The Apartment at Dark Run Retreat

RohanRating, 5 stars1 week ago
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.
Superhost
Apartment in Rockwood
4.89 out of 5 average rating, 193 reviews

Rustic Ranch Guest Apartment

PeterRating, 5 stars2 months ago
Great spot, very cozy and large! Accurate description and representative photos. I’ll be back next time I’m in the area!
Superhost
Apartment in Downtown Frederick
4.82 out of 5 average rating, 183 reviews

Lena's Downtown Vintage Flat with Parking

AnnetteRating, 5 stars1 week ago
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.
Top guest favorite
Apartment in Downtown Frederick
4.99 out of 5 average rating, 151 reviews

Carroll Creek Private Apt./Luxury King Bed

MikeRating, 5 stars2 weeks ago
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.
Top guest favorite
Apartment in Salisbury
4.96 out of 5 average rating, 127 reviews

Ord St Inn Unit Two, spacious 2nd floor apartment

ChristopherRating, 5 stars1 week ago
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.
Top guest favorite
Apartment in Broadway
4.99 out of 5 average rating, 227 reviews

Shenandoah Valley apartment with view

SelinaRating, 5 stars1 week ago
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.
Top guest favorite
Apartment in Harrisonburg
4.98 out of 5 average rating, 254 reviews

Spacious and bright 1 bedroom apartment near EMU

WenjuanRating, 5 stars4 weeks ago
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.
Superhost
Apartment in Berkeley Springs
4.88 out of 5 average rating, 107 reviews

1 Bedroom Apartment in Downtown Berkeley Springs

ChristineRating, 5 stars6 months ago
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

Guest favorite
Condo in Warrenton
4.93 out of 5 average rating, 101 reviews

Historic Two Bedroom in Old Town Warrenton

JeanRating, 5 stars4 days ago
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!
Guest favorite
Condo in Frederick
4.94 out of 5 average rating, 138 reviews

Quiet Apartment, Hot Tub, Downtown Frederick, Dogs

MarissaRating, 5 stars2 weeks ago
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.
Guest favorite
Condo in McGaheysville
4.84 out of 5 average rating, 144 reviews

Massanutten Woodstone 2-BR, 2 Bath

OsvaldoRating, 5 stars4 months ago
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.
Superhost
Condo in Mount Jackson
4.8 out of 5 average rating, 99 reviews

The Room with the Views!

AhmedRating, 5 stars2 months ago
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.
Superhost
Condo in West Springfield
4.83 out of 5 average rating, 203 reviews

Beautiful 2BR/1BA Renovated Condo near DC

AaronRating, 5 stars2 weeks ago
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!
Superhost
Condo in Downtown Frederick
4.78 out of 5 average rating, 9 reviews

Lark's Nest on Market

KathleenRating, 5 stars12 months ago
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.
Guest favorite
Condo in Occoquan
4.92 out of 5 average rating, 472 reviews

The Daisy in Historic Occoquan (Mins to DC)

KaraRating, 5 stars1 month ago
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!!
Guest favorite
Condo in Basye
4.82 out of 5 average rating, 28 reviews

Mountain views, quiet & relaxing, pet friendly

KyrstenRating, 5 stars1 week ago
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

Destinations to explore