Holiday rentals with a patio in Winchester

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Top-rated rentals with patio in Winchester

Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Downtown Frederick

4.89 out of 5 average rating, 111 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 favourite

Home in Elkton

4.95 out of 5 average rating, 184 reviews

Hottub 5 acres, Great hiking,The best views around

Stony Creek Lookout is a one-of-a-kind luxury retreat perched in the serene seclusion of the mountains.Brand new complete renovation, modern amenities, hot tub, sizable elevated deck, video/board games, theatre room, kayaks and high quality furnishings !This extraordinary stay adjoins the Shenandoah NatlPark with the best views in the Shenandoah Valley, hike out your back door. Pet friendly, 5 min from Massanutten 4 season resort, Shenandoah River & much more. Great Wifi & cell service! 5 TVs

Top guest favourite

Cottage in Woodstock

5 out of 5 average rating, 24 reviews

Riverfront Cottage~Hot Tub and Mountain View

The Misty River Cottage is located on one of the seven bends of the Shenandoah River and at the base of the Massanutten Mountain. It was designed, built and furnished with the goal of being one of the nicest options in the Shenandoah Valley. With views of the river and mountains from every room. Ensuite bathrooms in each of the two bedrooms. A custom built bunk bed for larger groups. Heated floors, spectacular outdoor space and direct river access all within a short drive to Woodstock.

Top guest favourite

Cabin in Basye

5 out of 5 average rating, 26 reviews

New Luxe cabin w/hot tub, fire pit & 4 season room

Welcome to Picard Place. This luxury 3 bed, 2 bath Chalet is peacefully situated 3 minutes from the Bryce Ski Resort & sleeps up to eight. Complete RENOVATION; fresh paint, comfortable & luxury furnishings, new kitchen, etc. And should you choose to venture out for adventure you’ll find yourself just 3 mins away from a great resort offering mountain biking, golf, winter sports, & scenic chair lift rides. Or pop over to Lake Laura (8 mins) for water activities or a stroll along the lake.

Top guest favourite

Flat in Meyersdale

4.97 out of 5 average rating, 175 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!

Top guest favourite

Tiny home in Harpers Ferry

4.98 out of 5 average rating, 105 reviews

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. The property features a large patio, outdoor dining area, courtyard, firepit, hammock, hot tub. The outdoor space provides private vistas of the Shenandoah, moonlit nights, star gazing while soaking in the hot tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

Guest favourite

Apartment in Centreville

4.91 out of 5 average rating, 101 reviews

Peaceful resort- like patio condo

Stylish 1 bedroom condo on ground level with 1 designated parking space directly in front. This home provides a perfect setting for both luxurious and comfortable living. Bright southern exposure, No steps from parking, 2 smart TV, Highspeed internet, queen size bed, the patio opens to private green nature. Plenty of guest parking as well. Long paved walking trail passing by, Walk to Giant, Starbuck, and Restaurants. Less than 2 miles from Spa World. And 10 min drive to King Spa.

Top guest favourite

Cabin in Berkeley Springs

4.98 out of 5 average rating, 110 reviews

Monte Vista~Golf~Views~PS5~Sport Court~EV Charger

IG @montevistawv Luxury Getaway Professionally Designed for STR 🏔️Massive Panoramic 3 State View 🏌️‍♂️Golf Ball Driving Range 🏀 Pickleball, Basketball, Volleyball & Tennis 🎮 PlayStation 5 Mini Disc ♨️ 6-Person Hot Tub 🔊Sonos Sound Throughout 🔋Level 2 EV Charger 🥾 Hiking Trail on site 🌳 33 private acres, no quiet hours 🔥 Massive Firepit + Grill & Pizza Oven 🛋️ Cozy Gas Fireplace 🌐 Fast WiFi & Three 65" Smart Tvs 🛏️ 3 King Beds & Twin Bunk Bed 💼 Dedicated Work Area

Guest favourite

Cottage in Leesburg

4.93 out of 5 average rating, 138 reviews

Hilltop @ Shiloh

Hilltop sits on a park-like estate. NEWLY REMODELED to be a two-unit dwelling. Enjoy beautiful views with rolling hills, ponds, and lush green landscaping. Come to just stay and refresh your soul in our peaceful Cottage or GO! 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, 11 miles to Morven Park, or 15 miles north to historic Frederick, Maryland.

Guest favourite

Home in McGaheysville

4.91 out of 5 average rating, 150 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!

Top guest favourite

Home in Leesburg

4.99 out of 5 average rating, 87 reviews

Quaint Royal Cottage @ Historic Leesburg

Welcome to the Quaint Royal Cottage, a beautifully appointed home nestled in one of Historic Leesburg's most desirable neighborhoods. Just a short stroll away, you'll find an array of dining options ranging from gourmet restaurants to casual eateries, along with numerous brewpubs and vibrant nightlife spots. After a night out, retreat to the serene backyard oasis and relax by the fire pit. Your delightful stay is guaranteed!

Guest favourite

Cabin in Rileyville

4.94 out of 5 average rating, 148 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