Holiday rentals in Winchester

4.99 out of 5 average rating, 405 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...

4.82 out of 5 average rating, 128 reviews

The Comfortable In-Towner

A cute one bedroom apartment located on lower level of a historic 1840s home. This half basement has windows to let in natural light, a full-size kitchen with dishwasher, fridge, big closets, Queen size Tuft & Needle premium mattress and a private screened patio open to our courtyard with friendly neighbors and management on site. Window ac units, fans & radiators Quiet neighborhood in Old Town Winchester, Va, two short blocks from pedestrian mall with restaurants, shops cafes & entertainment.

4.9 out of 5 average rating, 351 reviews

Downtown 1920's Gas Station with Hot Tub

Luxury 1920’s Refurbished Gas Station and hot tub repurposed into a beautiful apartment. Private parking/EV charging station, private hot tub, full kitchen, custom rain shower, high speed wifi, and smart TV. There is plenty of light with frosted garaged doors, all modern appliances, coffee nook, and an open living design. Be a part of Old Town Winchester in this unique getaway, walking distance to shops, downtown eateries and our neighborhood Pizzoco Pizza Parlor one block away. Pets welcome!

4.97 out of 5 average rating, 196 reviews

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

5 out of 5 average rating, 208 reviews

Old Town Loft In Highly Desirable Area Downtown

Location, Location! A completely renovated apartment in the highly desirable center Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.

4.97 out of 5 average rating, 282 reviews

Downtowner

No hassle parking on premises and a private entrance. The "Downtowner" is a 1920's era restored home in a quiet residential section of Winchester's Historic District and just a short stroll to the downtown "pedestrian only" walking mall with restaurants, cafes, and shops. Clean and spacious, the apartment is complete with bed linens, towels, etc. and stocked with water in the fridge as well as a Keurig with coffee options, tea, hot chocolate, etc...Xfinity HDTV with voice remote control.

4.73 out of 5 average rating, 656 reviews

Loft in Winchester

Immerse yourself in Old Town Winchester (Apt #4)

Our loft apartment is in the heart of Old Town Winchester on the Old Town Mall. Located off of a little alley, with security lighting and motion detectors you will be staying steps away from dining, shops, and everything our community has to offer. Yet, our apartments are quiet and secure. Our building is OLD & has all of the charm that goes along with it. If you are looking for a sparkly new place, you may want to stay elsewhere, If you want clean, funky, and awesome, we are your place!

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.

4.95 out of 5 average rating, 188 reviews

Indigo Blue modern open vibe on tree lined street

Come stay in this lovely spacious downtown home located on a beautiful tree lined street. Enjoy its open mid century modern style and relaxing outdoor areas! This 3BR 2BA home w/ sunroom w/ gas fireplace & rear fully fenced courtyard is the perfect place get away to & explore downtown Winchester. Walking distance to everything. Park & walk & enjoy nearby John Handley HS /walking mall /shopping/live music /art galleries/ walk to the iconic Handley Library, You will LOVE it!

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.

4.93 out of 5 average rating, 243 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, 498 reviews

Cottage in Winchester

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Popular amenities for Winchester holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Winchester

Private room in Winchester

4.77 out of 5 average rating, 188 reviews

Cheerful one bedroom available.

KenRating, 5 stars1 week ago

Great place to stay in a nice town. Made very welcome on arrival. Close to stores and food for convenience but not so close to disturb a quiet neighbourhood.

Private room in Winchester

4.98 out of 5 average rating, 111 reviews

Winchester Private Room

ThomasRating, 5 stars1 week ago

Beautiful room, with wonderful little touches like snacks, water bottles, and coffee, and as usual her two dogs are friendly and love a little bit of attention. Holly also provided a great recommendation of Bonnie Blue for some southern style dishes. It was sweet to have a comfortable place to crash and unwind after wandering civil war battlefields and museums.

5 out of 5 average rating, 58 reviews

Downtown Chic Condo w/parking

DanitaRating, 5 stars3 days ago

Lori and Myah were fantastic hosts. The place was super clean and beautifully decorated. Response time was super fast, and instructions were very easy to follow. I’d recommend everyone to stay here, and I will be staying again!

5 out of 5 average rating, 52 reviews

Large Historic Stone Home in the Heart of Old Town

PatRating, 5 stars1 week ago

I rented this out for my son, daughter and their families while they were in town visiting me. They loved the space and were impressed with the outdoor area and different sitting areas. It was so convenient to the restaurants and the walking mall.

4.86 out of 5 average rating, 7 reviews

Sophisticated 4BR: Chef's Kitchen, Grill, Patio

PederRating, 5 stars2 months ago

We really enjoyed our stay in this house and Suranny was very responsive and helpful. The house was clean as can be and very spacious. Lots of natural sunlight and a wonderful covered porch to sit out on. The beds were very comfortable and the bathrooms were clean. We would certainly stay here again in the future.

4.9 out of 5 average rating, 10 reviews

Skyview Farmhouse

SaraRating, 5 starstoday

We had a wonderful stay at Denise’s farmhouse with our family. Her house is beautiful, very clean, and extremely comfortable and inviting. She has thought of every detail and includes extra amenities like snacks, toiletries, board games, and plenty of linens. We had our young son with us, and she laid out many things for him like a portable crib, baby shampoo and towels, a bathtub, and a changing pad. The location is beautiful and not far from restaurants, shops, etc. All the beds and furniture were very comfortable, and there was plenty of space for everyone. As a host, Denise was extremely responsive and made things very easy for us. I would recommend her house to anyone!

Private room in Winchester

4.92 out of 5 average rating, 216 reviews

We Welcome You to Winchester! Best reviews!

NickieRating, 5 stars1 week ago

Gary and Wendy’s place was absolutely lovely! Very clean. Gary was so kind and met me for check-in even though he and Wendy were staying somewhere else for the weekend. I felt very at home. Would definitely stay again!