Vacation rentals with a patio in Winchester

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Top-rated patio rentals in Winchester

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Guest favorite

Condo in Downtown Frederick

4.9 out of 5 average rating, 101 reviews

Newly Renovated HUGE condo in heart of downtown!

Our brand new totally upgraded and renovated condo is in the heart of downtown Frederick’s main square. The whole group will enjoy easy access to everything from this centrally located place. This unique historic building has a private parking spot, and access to prime shopping and dining just steps from your door. Although this is an apartment, don’t let it fool you! This 2,000+ sq foot beauty will give you enough space to spread out and relax! This building has the ability to sleep 16!Ask host

Guest favorite

Guest suite in Front Royal

4.99 out of 5 average rating, 113 reviews

Chapel View Nest: Patio, Firepit and Views.

Stay in our secluded getaway on 20 acres with skyline mountain views and stunning sunsets. The main house is perched atop a hill with the English basement attached. Guests will have their own private sunny patio with a gas fire pit and grill. Relax and unwind in this welcoming tucked away spot that is private and tastefully furnished with everything you need for a wonderful stay. Nearby: Christendom College ~1 m Warren Memorial Hospital 2.5 m Shenandoah Park Skyline Dr. 6 m Front Royal 6 m

Guest favorite

Cottage in Leesburg

4.92 out of 5 average rating, 121 reviews

Hilltop @ Shiloh

**Hilltop sits on a park-like estate. Originally a barn, Hilltop has been NEWLY REMODELED to be a two-unit dwelling. Enjoy beautiful views with rolling hills, ponds, and lush green landscaping. Come stay and refresh your soul in our peaceful Cottage or GO and have fun! Convenient to breweries, wineries, C&O Canal for biking or hiking, and antique shopping at the popular Lucketts Store. 11 miles south to historic downtown Leesburg, Virginia or 15 miles north to historic Frederick, Maryland.**

Guest favorite

Cottage in Shenandoah

4.97 out of 5 average rating, 186 reviews

Charming Cottage in the Heart of Shenandoah!

Cozy & inviting cottage less than 1 mile from public access to the Shenandoah River. Many attractions nearby: Shenandoah National Park, Massanutten Four Seasons Resort, Luray Caverns, George Washington National Forest, Lake Arrowhead and more! Enjoy tubing, canoeing, kayaking or fishing by visiting Shenandoah River Adventures (less than 1 mile away). Whether you are looking for outdoor adventures or a secluded getaway, this home offers all the amenities you'll need to have an enjoyable trip.

Guest favorite

Rental unit in Meyersdale

4.96 out of 5 average rating, 137 reviews

Country Home

Relax with family, friends, or enjoy a solo retreat at this peaceful place to stay in the country. Chestnut House was built in the early 1940s, with Wormy Chestnut wood everywhere! It is a unique home, with an apartment built over a garage / wood working shop.. then connected to the main house later. This space available to rent is separate and fully functional from the main house where we live. Enjoy 2 bedrooms, 1 bathroom, full kitchen and living area.. along with the large outdoors!

Guest favorite

Home in Quicksburg

4.93 out of 5 average rating, 122 reviews

Overbank Riverfront Estate~Hot Tub~Pool~Views

Brand New Listing! This renovated farmhouse on the Shenandoah River is the ultimate vacation spot. Relax on the new massive deck sitting above the Shenandoah River with the blue ridge mountains as your backdrop. Play in your own private pool. Dine on the wrap around screened porch. Paddle under historic Meems Bottom Covered Bridge. This 100 year old farmhouse has been renovated to add modern comfort to timeless charm. Venture out to the caverns, hiking, and wineries nearby.

Guest favorite

Home in McGaheysville

4.92 out of 5 average rating, 133 reviews

Pleasant Place near Massanutten Resort!

Located near Massanutten Four Season Resort, Pleasant Place offers everything you need for a comfortable stay. Whether you are looking for a weekend getaway or new views for your telework station, this property has it all. With an abundance of light, an outdoor firepit, and full deck dining, you are sure to get some much-needed relaxation in the mountains. Minutes away from Massanutten Ski Lodge, two 18-hole golf courses, year round indoor/outdoor water park, and more!

Guest favorite

Camper/RV in New Market

4.98 out of 5 average rating, 104 reviews

Peak season! Glamp before season ends!

Stay for an unforgettable glamping experience at this memorable location, in a vintage Airstream! Filled with all the extras! Wonderful coffee bar to enjoy while sitting on your private deck only steps from the bank of the pond. Amazing outdoor shower. Stocked fishing pond. No permit needed. Cuddle up by the fire admiring the starry sky, then off to bed, awaken fresh with sounds of nature. What more could you ask for? Coffee, peace & quiet! The PINNACLE of glamping.

Guest favorite

Home in Sabillasville

4.92 out of 5 average rating, 106 reviews

Stoney Spring Overlook

This beautiful mountain farm home has breath taking scenic views of the surrounding Catoctin mountain. There are many nearby outdoor activities, including scenic hikes, mountain biking, Ski Liberty, wineries and the Catoctin zoo. While it is a peaceful get away in the mountains, it is just 30 minutes away from the Frederick, MD and historic Gettysburg, PA. Whether you want to get away from the city or explore more of Maryland, this is the perfect stay for you!

Guest favorite

Rental unit in Downtown Frederick

4.96 out of 5 average rating, 134 reviews

King Bed Apt./Carroll Creek Promenade w/views!!

Enjoy the best possible location right on Carroll Creek Promenade in heart of historic downtown Frederick. Sit on your private porch and listen to concerts or enjoy the evening sunsets over the city. Private parking off street and walk right out to enjoy the city sights, events and amazing restaurants. King size bed & full kitchen plus two streaming TVs and free wi-fi. Romantic outdoor courtyard perfect for a romantic summer evening. Come see us and enjoy!

Guest favorite

Cabin in Front Royal

4.96 out of 5 average rating, 136 reviews

*Swanky Sexy w/ Hot Tub, River Views, & FUN*

Have fun at Starlight on the River! Chill vibe with high style and sexy romance! ***Hot tub and river views*** Pop meets mid-mod design, modern cabin meets urban flare! The most perfect one bedroom, hot tub, riverfront Airbnb you will find, only 60 minutes from Washington DC! From life size tigers to real eagles flying by, Starlight will be a memory to never forget! ~Treat Yourself to Starlight, You Deserve This! ~

Guest favorite

Cabin in Rileyville

4.93 out of 5 average rating, 124 reviews

A+ Privacy & Views | HotTub + Firepit + BBQ | Pets

Secluded mountain cabin with 2 kings, hot tub, fire pit & panoramic views! ★ "Amazing place… the views are breathtaking." ☞ 2 level deck w/ mountain views ☞ Complimentary SUV provided ☞ Hike to waterfall (20 mins) ☞ Fully equipped + stocked kitchen ☞ Patio w/ BBQ grill + dining ☞ 50” Smart TV w/ Netflix ☞ Indoor wood fireplace ☞ Pet friendly* 20 mins → DT Luray (cafes, dining, shops) 30 mins → Shenandoah National Park