Vacation rentals with a patio in Winchester

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Top-rated patio rentals in Winchester

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Guest favorite

Cottage in Winchester

4.98 out of 5 average rating, 305 reviews

Uber SXY Private Country Escape! Hot Tub & Views~

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

Oct 8 – 15

G$44,226 GYD per night

Guest favorite

Tiny home in Quicksburg

4.99 out of 5 average rating, 179 reviews

Finn's Frolic-The place- relax, stay, or explore!

Finn's Frolic is our charming, new country tiny home. Less than 2 hours DC, Charlottesville. Beautiful farm, mountain views, deck, fire pit, charcoal grill, much more. Landscaping is in the works ! Kitchen is fully equipped, vintage & new dinner wear. Living room has an electric fireplace, huge picture window, comfy love seat. The bedroom is up traditional stairs: loft bedroom, 7 foot sloped ceiling. Great place to relax, base for visits to local wineries, attractions! Perfectly imperfect!

Aug 5 – 12

G$17,770 GYD per night

Guest favorite

Guesthouse in Lovettsville

4.94 out of 5 average rating, 120 reviews

The Patent House

Built around 1760, our log cabin sits on our 3 acre farmette, in the countryside in view of the foothills that separate VA, WV & MD. It's fully renovated, with a master bedroom (queen), full bath & convertible sofa downstairs (full). The cabin is next door to our house & shares a fence with our pasture where our miniature donkeys live. We have yappy dogs and friendly outdoor cats. we're in the country, so bugs do make their appearance, but they tend to go straight to the window sills.

Aug 6 – 13

G$21,457 GYD per night

Guest favorite

Guest suite in Smithsburg

4.99 out of 5 average rating, 153 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, dog-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 4 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Sep 1 – 8

G$18,039 GYD per night

Guest favorite

Barn in Elkton

5.0 out of 5 average rating, 143 reviews

Elkton Dairy Barn near Shenandoah National Park

Were you raised in a barn? No! Us either but here’s your chance to stay in our cozy, converted dairy barn, perfect for a romantic getaway. For generations, the barn was used to milk the dairy cattle on our farmette nestled at the foothills of Massanutten Resort & the Skyline National Park. The Dairy Barn makes a perfect small gathering home place. Just wait until you see the views of the Blue Ridge Mountains from the lofted bedroom & the breathtaking foliage from the screened porch.

Aug 13 – 20

G$31,051 GYD per night

Guest favorite

Guesthouse in Myersville

4.93 out of 5 average rating, 190 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

Jun 30 – Jul 7

G$20,992 GYD per night

Guest favorite

Home in Bolivar

4.96 out of 5 average rating, 183 reviews

Newly renovated - Walk to Harpers Ferry NP

Kick back and relax in this newly interior renovated space on the corner lot of a very quiet neighborhood. It has 800 sq feet with full kitchen, living area, bath, remote work desktop with an ergonomic chair, deck, large fenced in yard, and a 24/7 convenience store one block away. It has a one bedroom with a Dream Cloud queen mattress on an adjustable bed. Located between Bolivar Heights NP and downtown Harpers Ferry. Please note that the living area for this home is upstairs.

Jul 27 – Aug 3

G$23,826 GYD per night

Guest favorite

Cabin in Lost River

4.96 out of 5 average rating, 112 reviews

Rustic and stylish mountain getaway

The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

Dec 28 – Jan 4

G$20,212 GYD per night

Guest favorite

Apartment in Shepherdstown

4.98 out of 5 average rating, 117 reviews

The 1763 House - Stay in Downtown Shepherdstown

Welcome to our charming downtown Shepherdstown apartment, originally built in 1763 and nestled in the heart of town. Ideal for getaways, visiting family/friends, or university trips. Enjoy a spacious interior, comfortable living room, state-of-the-art kitchen, and private patio. Our downtown location on the Main Street offers convenient access to a wide selection of restaurants, unique shopping, and the Potomac river, all just a short walk away!

Oct 1 – 8

G$34,805 GYD per night

Guest favorite

Guesthouse in Elkton

4.99 out of 5 average rating, 162 reviews

Noná’s Nest

Noná’s Nest is a quaint one bedroom, one bathroom carriage house, tucked into the peaceful Shenandoah Valley. Centrally located 9.5 miles to the Swift Run Gap entrance of Shenandoah National Park, 12 miles to Massanutten Resort, and 22 miles to Harrisonburg. Enjoy the tranquil country setting and beautiful Blue Ridge Mountain views from the second story deck. Owners live adjacent to carriage house.

Oct 15 – 22

G$19,348 GYD per night

Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 183 reviews

The GW Hollida Cottage of Shepherdstown

Let time slow just a bit at this unique and tranquil getaway! This recently renovated cottage is situated just behind the GW Hollida house, circa early 1800s. Whether taking a few extra breaths of fresh air on the deck, taking a stroll through the 5 acres of serenity, or kicking back to enjoy some peace and quiet, we are confident you'll love this place as much as we do!

Apr 12 – 19

G$25,257 GYD per night

Guest favorite

Cabin in Lost River

4.98 out of 5 average rating, 166 reviews

Design-forward cabin in the woods

We envisioned this one room, design-forward cabin as a space for solo travelers, couples, artists, writers, and their dogs to unwind, center the self in nature, and find deep focus. It quickly became our happy place. Windows on all four sides ground you on the fully wooded lot, and the view from the spacious back porch evolves into new art throughout every season.

Jul 9 – 16

G$30,732 GYD per night