Holiday rentals with outdoor seating in Frederick County

4.94 out of 5 average rating, 141 reviews

Home in High View

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fishing

Mountain home: like in the movies, on 50 acres. Includes soaring mountain views, swimming holes, hiking trails, ATV trails, fishing creek, mini white sand beach, hot tub in a cave, huge boulder rustic fire pits, cave, lake, cabanas, all in a secluded forest exclusively for guests. Private: you cannot see another house from the front porch or back decks and it has thick woods all around. At the top of the property are soaring views with 3 miles of visibility. No need to go to the national park.

4.88 out of 5 average rating, 651 reviews

Home in Inwood

Arden House, Inwood WV

Ground level two room unit. No steps. Separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed, sofa and full refrig.. In a separate living area, there is a queen bed, TV, bathroom, desk, table, microwave, convection oven, air fryer, gas fireplace. No oven. Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic.

4.99 out of 5 average rating, 407 reviews

Cottage in Winchester

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...

4.97 out of 5 average rating, 144 reviews

Cabin in High View

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

4.91 out of 5 average rating, 111 reviews

Scarborough Fair walk to downtown two story apt

Come to downtown Winchester get the true feel of the city. Park & Walk to beautiful Handley Library, take a stroll to the much loved walking mall to the many shops & restaurants. Scarborough Fair is the place to enjoy the time w/family and friends. Three bedrooms, two levels, three porches, fenced yard. Eclectic & comfortable you will love your stay in this wonderful spot downtown. Looking for more space? or have any additional questions? Reach out on social media: Michele Bouve Hoffman.

4.99 out of 5 average rating, 155 reviews

Cabin in Gerrardstown

The Nest: Cozy Chalet w/Wi-Fi, Deck & Grill

The Nest is a chalet-style cabin tucked into the tree-lined mountains of Berkeley County, WV. It offers adventure, a quiet retreat & good family fun. With 5-acres in the countryside, you'll enjoy star studded skies on clear nights & wake up to birds singing & deer wandering, with mountain views through vaulted windows. The Nest is near Martinsburg, Berkeley Springs, Harpers Ferry, Shepherdstown, Charles Town & Cacapon State Park, among other go-to destinations on the Eastern Panhandle.

4.97 out of 5 average rating, 254 reviews

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

Guest suite in Winchester

4.81 out of 5 average rating, 339 reviews

Safe, cozy oasis with private living & bath.

Wonderfully comfortable basement apartment. We are less than a mile from Winchester Medical Center.... ideal for traveling doctors/nurses. Close to other area attractions. You will have your own living room, bathroom and bedroom. Private entrance. Digital lock. You will get instructions prior to check in. You will be in the basement however it has natural light in the bedroom. There may be some noise from upstairs, but it is generally quiet.

4.99 out of 5 average rating, 179 reviews

Cabin in Star Tannery

Cabin With Wood Burning Hot Tub

Escape to our modern cabin on 12 private acres. Unwind in the wood-burning hot tub, embracing the surroundings and stars at night. With a contemporary design and natural light, this retreat blends with nature. Explore private trails throughout the property, enjoying nature and the fresh air. Inside, find comfort in the fully equipped kitchen and cozy living area. Perfect for a peaceful getaway, our secluded home provides privacy and relaxation.

4.93 out of 5 average rating, 245 reviews

Townhouse in Winchester

Modern Elegance in Historic Old Town Winchester

Just a block and a half from the Old Town Winchester pedestrian mall, this historic beauty with modern elegance is sure to please. You are within walking distance of quaint shops, great restaurants, The Brightbox Theater, and The Shenendoah Discovery Museum. Spend the day touring the areas great wineries or enjoying Skyline Drive, and then return to enjoy a great night out, or an evening at home making dinner in the spacious modern kitchen.

4.97 out of 5 average rating, 233 reviews

Full basement with private entrance. Hot tub

Cozy movie themed basement is exactly what you are looking for. Classic AirBnB-we are opening our house to you! Space is completely private. Bedroom with queen bed. High speed internet. Private bath w/shower. Small refrigerator, microwave, 2 flat screen TVs table and chairs and multiple couches in a large family room w/Sofa bed. 1000 square feet of space! Home 2 miles outside of the city of Winchester in Frederick County.

4.96 out of 5 average rating, 129 reviews

Aunt Tim's Farmhouse

Our farmhouse is located approximately 5 miles west of Historic Winchester, VA. The house is situated on 106 acres of an operational farm. You may see family members and friends tending honey bee hives, working in the detached garage, gardening, and completing other farm chores. The house is solely occupied by our guests. Come on out to enjoy some peace and quiet and take advantage of all Mother Nature has to offer!

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House rentals with outdoor seating

4.9 out of 5 average rating, 48 reviews

Home in Berkeley Springs

The Hidden Gem of of Berkeley Springs

MaryannRating, 5 stars3 weeks ago

We thoroughly enjoyed our stay at Matthew’s retreat. The home is spacious across both levels, making it perfect for our large family. It’s beautifully furnished-comfortable, tasteful and uncluttered. The kitchen is generously equipped. The massive deck is a real highlight. With plenty of seating, two heaters and a grill. The peaceful surroundings made it easy to connect with nature and truly unwind. Check-in and check-out were easy. The house is exactly as advertised- no surprises, just a great experience. Five stars, Matthew, we are so glad we found your place/

4.94 out of 5 average rating, 88 reviews

Home in Gore

The Eagle's Nest at Ice Mountain

DanaRating, 5 stars6 months ago

Alex was very friendly and responsive. The place was large enough for 5 adults, 4 teens, and a dog to spread out and have a nice time. The location was lovely, and the home was very welcoming.

4.98 out of 5 average rating, 42 reviews

Home in Yellow Spring

River Perch on the Cacapon River in Capon Bridge

AlexandraRating, 5 stars2 weeks ago

My husband, two young children and I stayed for a weekend, and it was amazing! The house and area was beautiful. There was a fire pit within walking distance, and Glenn gave great details on the best place to go kayaking and tubing along the river. Glenn was an amazing host, and he gave great recommendations on what to do in that area. If you have smaller kids who just love to run around outside this is a great place!

4.94 out of 5 average rating, 155 reviews

Historic District Charm On Cameron Street

StaceyRating, 5 stars1 month ago

I’ve had the wonderful opportunity to stay at Elizabeth’s place a few times and it’s one of my favorites! It is so homey, spacious, and the location is fantastic! Elizabeth is a fabulous host…great communication and very personable. This last stay in late May was very special because my son graduated from Shenandoah Conservatory. Highly recommend to stay here!

4.94 out of 5 average rating, 99 reviews

Home in Gerrardstown

A-Frame Mountain Retreat

DavidRating, 5 stars1 month ago

I loved this place! Very clean, comfortable, and peaceful inside and outside!

4.85 out of 5 average rating, 75 reviews

Springdale Mill Farmhouse with Spa House

MonfordRating, 5 stars6 months ago

The place was perfect for our family. Stacey was fantastic and very responsive. Definitely recommend this Airbnb.

4.76 out of 5 average rating, 270 reviews

Home in Strasburg

Cedar Creek Wayside Castle

TraceyRating, 5 stars1 month ago

I needed a place that my family, from out of state, could stay while attending a graduation. The house was perfect! I told Bob what I wanted to do and he was encouraging and helpful. He made sure we had propane for grilling and answered all my questions. He was very prompt when I reached out to him. We had an amazing time. I would stay there again.

5 out of 5 average rating, 33 reviews

Whole 3-bedroom house walkable to downtown.

GiniRating, 5 stars2 months ago

We thoroughly enjoyed our extended stay in this charming cottage! The location is ideal for walking—- either around the neighborhood or downtown. We loved the charm and cozy atmosphere and spent a lot of time on the sun porch too! Can’t recommend it highly enough and look forward to staying here again

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Apartment rentals with outdoor seating

4.8 out of 5 average rating, 294 reviews

Pretty Little Apt by the Train II

RobertRating, 5 stars10 months ago

Perfect apartment. Close to everything and Michele was the perfect hostess. I needed a place near my school where I teach while my house was undergoing renovations and Michele provided a safe, comfortable abode. Thank you Michele.

4.79 out of 5 average rating, 120 reviews

Yellow Submarine trendy basement apt w/courtyard

HeatherRating, 5 stars2 weeks ago

Sweet downstairs apartment very close to downtown Winchester. Comfortable, clean and fun decor. Michele was responsive and helpful. Just one note, to read the description clearly about the sleeping arrangements. It's all there in the listing, but we were still a little surprised (our fault). There is one private bedroom. There is a second bedroom that doesn't have a door. The only bathroom is accessed through the second bedroom. The third bed is behind a divider in the living room. It all worked fine for us, but might not for folks that require privacy.

4.75 out of 5 average rating, 225 reviews

Pretty Little Apt by the Train I

ColleenRating, 5 stars25 months ago

This was a great place to stay to experience Winchester, super close to restaurants and the Old Downtown. Small and quaint space, more than enough for the two of us who stayed there. Not noisy in the bedroom at all, but there is a bar across the street that is open till 1am on weekends, which was not a problem at all for my boyfriend and I who joined in on the fun. Michele was super helpful and responsive during our stay. This place was worth the price. Overall, great place!