Vacation rentals with a patio in Winchester

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Popular amenities for Winchester patio rentals

Apartment rentals with a patio

Superhost
A misty landscape is viewed from a covered patio, featuring expansive green fields and trees in the distance. A light rain is visible, creating a soft ambiance across the scenery. The structure's railing and patio furniture frame the tranquil rural setting.
Apartment in Culpeper
5 out of 5 average rating, 4 reviews

Private Patio Apartment Hosted by Gary

ChristinaRating, 5 stars5 months ago
Peaceful, the horse's were beautiful to look at everyday, it hasa relaxing feel and I worked third shift at the hospital and no complaints at all.
Superhost
A welcoming living area displays a large sectional sofa and a comfortable armchair, paired with a marble coffee table. Natural light filters through multiple windows and a modern fireplace is situated below a mounted television, enhancing the overall atmosphere.
Apartment in Frederick
4.87 out of 5 average rating, 15 reviews

Luxury Basement Apartment Suite

AlexRating, 5 stars9 months ago
Stay was exactly as described. Home was clean and had everything needed for a home base for work and camp for the kids. Jorge and John we very communicative and friendly. 100% would reccomend.
Guest favorite
A serene riverfront scene is displayed, featuring a lush green lawn that leads to a calm waterway. Several chairs are arranged near the water's edge, with a picnic table visible in the foreground. Trees provide natural shade, enhancing the peaceful setting.
Apartment in Elkton
4.88 out of 5 average rating, 102 reviews

Rustic River Retreat- 2 Bedroom Riverfront Lodging

JuanRating, 5 stars3 months ago
It is a really nice, peaceful place, with beautiful surroundings, great host, place is close to many outdoor activities.
Top guest favorite
A corner seating area features two plush gray armchairs beside a small round table. Natural light enters through a window adorned with sheer curtains, while a decorative plant and a cozy blanket add subtle touches to the space.
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
A covered patio area is presented with a picnic table and a decorative rug. Lush flower beds filled with vibrant blooms line the space, adding color and charm. A small wooden chair enhances the inviting outdoor setting.
Apartment in Hagerstown
5 out of 5 average rating, 121 reviews

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5

NevaehRating, 5 stars1 week ago
(For younger people that care), beware that they live upstairs from where you will be staying!!! We (kinda of) loudly played music in the living room, were able to walk 50 feet to the gazebo (located in the yard) to smoke, and laughed loudly all night. We were worried we’d have to be super quiet and they would be strict but, the owners had no complaints which we were very greatful for, didn’t interrupt us, got our money’s worth and had a great night!
Guest favorite
A compact kitchen area features modern appliances, including a microwave and small refrigerator, along with a sink. Two stylish bar stools are positioned at a countertop. The space opens into a well-lit living area, with the bedroom visible in the background.
Apartment in Downtown Frederick
4.93 out of 5 average rating, 102 reviews

Charming Historic Downtown Apartment…The Fox’s Den

MatthewRating, 5 stars2 weeks ago
We had a wonderful stay! The place was as nice as the pictures showed. Roomy yet cozy, and comfortable. Bedrooms on opposite sides so that two couples can share the place. Good location only a short walk to downtown. Two parking spots not far from the entrance. Well-lit neighborhood and home, felt very safe.
Guest favorite
The studio apartment features a cozy sleeping area with a wooden bed framed by colorful bedding. A sitting area includes a red table and chairs, accompanied by a blue side table and lamps. A large closet with white doors offers ample storage space.
Apartment in Fredericksburg
4.94 out of 5 average rating, 31 reviews

Downtown Private Apartment

JoeRating, 5 stars5 months ago
Perfect location for someone interested in historical sites. I was notified in the morning that the space would be available earlier than scheduled. Bedroom was large with ample closet space. Kitchen was adequately equipped. It has a drip coffee-maker and coffee, sugar, and non-dairy creamer. Kitchen table only seats two. Shower stall was roomy. Bring your own detergent if you intend to use the laundry machines. I was quite satisfied.
Top guest favorite
A comforting sleeping area features a spacious bed topped with a patterned quilt. A soft cloud-shaped pillow adds a touch of whimsy. Light flows through a window adorned with soft shades, with a small round table nearby, enhancing the inviting ambiance of the room.
Apartment in Front Royal
4.98 out of 5 average rating, 107 reviews

Cozy 1BR for Couples & Solo Travel~No Cleaning Fee

MorganRating, 5 stars4 days ago
This apartment was absolutely cozy! I've never stayed in an Airbnb that is a part of someone's house, and I felt very comfortable with my stay. On top of that, the space was noticeably pristine! We happened to meet Erika and John in passing and they were extremely pleasant. Since the weather has been changing, Erika made a point to ask about the temperature in the apartment and quickly followed up by providing us a fan to keep us cool! The aesthetic in the apartment is super cute, especially if you like cats. We felt calm and at-home in this space. Would definitely stay again if we come out to Front Royal! P.S., ask Erika about cool and vintage spots nearby ;) She's got all the info!

House rentals with a patio

Top guest favorite
A scenic view of rolling hills is captured, showcasing vibrant autumn foliage across the mountains. A grassy field stretches in the foreground, bordered by a black wooden fence. The sky displays soft pastel colors, hinting at a peaceful evening.
Home in Stanardsville
4.96 out of 5 average rating, 26 reviews

The Madelyn

Narasimha KamalRating, 5 stars1 week ago
very good place, close to the park. peaceful and had more entertainment in house. Netflix, Youtube
Superhost
An open dining area features a large table surrounded by wooden chairs. Natural light fills the space through sheer curtains. A wall clock and a large television complement the room, while a decorative plant adds a touch of greenery in the corner.
Home in Fredericksburg
4.84 out of 5 average rating, 57 reviews

Relax in cozy 4 br 2 bath split foyer hse in Fburg

CarlanthaRating, 5 stars2 months ago
Manny was super responsive to our needs and communicated well throughout our stay. Our stay here was definitely well worth it and was exactly what we were looking for.
Top guest favorite
A bright living area features a light grey walls and sleek wood flooring. Comfortable seating includes a sectional sofa with decorative pillows, complemented by a blue chair. A coffee table sits atop a soft area rug, while large windows provide natural light, framed by patterned curtains.
Home in Stanardsville
4.96 out of 5 average rating, 57 reviews

Cozy Corner Getaway

BrittanyRating, 5 stars6 days ago
We enjoyed our stay at the Cozy Corner! The area was beautiful, quiet, and peaceful. Having the fenced in backyard was a huge bonus with our dog and son. The house was clean and had everything we needed for our stay. We would definitely come back and stay here again!
Guest favorite
A covered patio area features four comfortable lounge chairs, each with soft cushions. A small side table stands beside one of the chairs. The brick exterior provides a warm backdrop, while two windows allow natural light to fill the space.
Home in Cumberland
4.89 out of 5 average rating, 27 reviews

Johnson Heights Getaway

KatieRating, 5 stars1 month ago
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!
Superhost
The one-story home features a red brick exterior accented by black shutters. A welcoming front porch is furnished with rocking chairs, and a pathway leads to the front door. The surrounding yard is green with trees and shrubbery, providing a serene atmosphere.
Home in Fredericksburg
4.71 out of 5 average rating, 78 reviews

Cozy Home Close to Downtown/I-95

LoganRating, 5 stars2 weeks ago
House was nice, the book selection was pretty cool. There was a book for Cape Cod, which we were heading too after our stay.
Top guest favorite
The exterior of the duplex features a welcoming facade with a large front porch adorned with rockers. A wide pathway leads to the entrance, flanked by manicured greenery. Tall trees surround the property, providing a natural backdrop beneath a clear blue sky.
Home in Locust Grove
4.96 out of 5 average rating, 52 reviews

Newly Built Secluded Duplex-Left Side Unit

RebeccaRating, 5 stars1 day ago
We have stayed at Christina’s duplex multiple times and the overall accommodations are consistently excellent. Christina is friendly, welcoming, and accommodating. We highly recommend Christina’s duplex to anyone staying in the Locust Grove area!
Guest favorite
Home in Purcellville
4.93 out of 5 average rating, 28 reviews

Recently Renovated Rolling Hills Retreat

CarolRating, 5 stars3 days ago
Our son got married at the Still Meadow wedding venue right across the road. With four bedrooms, plus an extra bed downstairs, we were able to accommodate 8 members of our family, so our stay also became a family reunion of sorts. Perfect! Spacious eat-in kitchen and great set up in living room made it easy to enjoy some games and catch up! Beautiful big deck looking out over the countryside! Three bathrooms, hairdryers and mirrors made wedding prep easy. Really appreciate dog friendly house. So did our dog! Lots of extra blankets for beds in case we were chilly. Would definitely return to this gorgeous area and highly recommend Jill’s house!!
Superhost
A charming single-story home features brick exterior with a front porch bordered by white railings. The well-maintained lawn is enhanced by neat flower beds and a stone pathway leading to the entrance. Lush greenery provides a natural backdrop, contributing to a welcoming ambiance.
Home in Berryville
4.91 out of 5 average rating, 33 reviews

Rustic chic 3 bedroom home with onsite parking.

ChristinaRating, 5 stars1 day ago
Once again, Donna was the perfect host. The house and its location are perfect for us. Recommended for sure.

Condo rentals with a patio

Top guest favorite
A large, dark green sign displays 'Northern Lights Village' in bold white letters. The sign is situated amidst snow-covered ground, with leafless trees and distant buildings in the background, conveying a winter landscape.
Condo in Mercersburg
5 out of 5 average rating, 20 reviews

SlopeSide

JenniferRating, 5 stars2 months ago
I almost don't want to write a positive review because I'd like this condo to be available only to me. It was perfect! The place is comfortable and had everything we needed for our 2 night stay. Easy ski in/out access, and perfect for a family that has some that stay on the slopes a little longer than others. We just hope this place will be available again when we visit next.
Guest favorite
An outdoor dining area is visible on a private brick patio, featuring a table surrounded by chairs. A large umbrella offers shade. Lush greenery and trees are seen beyond the patio, with a charming brick building in the background.
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!
Top guest favorite
A light-filled living area features a spacious sectional sofa paired with two side chairs. A wooden coffee table is centrally positioned on a soft area rug. Large sliding doors lead to an exterior space, while a smart TV is mounted against the wall.
Condo in Bridgewater
4.98 out of 5 average rating, 110 reviews

Wi-Fi, 3 bedroom, 3 bath, near BWC, JMU, 1-81

SarahannRating, 5 stars1 week ago
This was the second time we have stayed her, and hopefully, won’t be the last.
Guest favorite
A secluded backyard space features a wooden dining table adorned with decorative items. Colorful umbrellas provide shade over the patio area. String lights create a soft glow, complementing a small fire pit surrounded by chairs, enhancing the inviting atmosphere of the outdoor setting.
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.
Superhost
The living area features a stone fireplace, complemented by a stack of firewood beside it. A large leather sofa and a sleek black armchair surround a round table, while expansive windows provide natural light and views of the outdoors.
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.
Guest favorite
A cozy living area features a spacious sectional sofa adorned with patterned cushions. A round table is accompanied by wooden chairs, while a minimalist coffee table sits on a plush area rug. Natural light enters through multiple windows, highlighting the room's inviting design.
Condo in Leesburg
4.93 out of 5 average rating, 190 reviews

Stunning Remodeled 1 BR Condo Steps to Everything.

BrittaniRating, 5 stars6 months ago
We had a wonderful night at the condo. Our host let us know in the morning it was clean and ready so that we could check in early. Very clean and comfortable. Would stay here again for sure.
Superhost
A stone patio area is highlighted with a large parasol providing shade over a dining set, featuring four chairs and a table. Surrounded by flower pots, a lush green lawn is visible in the background, with trees providing additional shade.
Condo in Culpeper
4.92 out of 5 average rating, 13 reviews

Private 2/2 full baths very bright basement home

KariRating, 5 stars6 months ago
We had a lovely stay at Lili's place. It was very peaceful! We would definitely book again if we were in the area. Lili was very responsive to any questions we had.
Guest favorite
This historic brick building features a balanced façade with multiple windows and a gabled roof. The structure is complemented by surrounding trees and a parking area. Parked cars line the street, indicating an accessible location in a bustling downtown area.
Condo in Fredericksburg
4.95 out of 5 average rating, 242 reviews

Casa 1776 - Spacious Apartment | Heart of Downtown

SuzanneRating, 5 stars3 weeks ago
Jordan & Veronica’s place was cozy, clean, peaceful, and in the perfect location! The description was spot on and the amenities (an iron!! and water/snacks) were great. Walkability in the downtown area and to UMW were perfect for our visit. We hope to return!

Quick stats about vacation rentals with a patio in Winchester

  • Total rentals

    50 properties

  • Nightly prices starting at

    $20 before taxes and fees

  • Total number of reviews

    3.6K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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