Holiday rentals in Stephens City

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Top-rated holiday rentals in Stephens City

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Guest favourite

Flat in Capon Bridge

4.99 out of 5 average rating, 114 reviews

Paw Paw Suite ~ 1 of 5 Unique Stays at Basswood

For those seeking to step away from the bustle of the city and slow down in a friendly, charming town. Basswood is a historic home that has been lovingly remodeled to include five private suites each with their own unique style. The Paw Paw Suite is an inviting space with a queen size bed, double shower bathroom, and kitchenette. Located in the heart of Capon Bridge, you'll find it easy to walk to everything. For a relaxing stay in a friendly, artsy community, this is a great place to enjoy.

4–11 Oct

₹7,042 per night

Guest favourite

Home in Winchester

4.97 out of 5 average rating, 166 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 !

3–10 Jan

₹10,893 per night

Guest favourite

Flat in Winchester

4.87 out of 5 average rating, 154 reviews

Downtown FUN! Personal Mid Century 2bd Apartment!

Welcome to Blossom! Your own, private pied-à-terre, located in Winchester's historic district, 1 block from the Old Town Walking Mall! Blossom's UBER-LUX upgrades include a fully-stocked custom kitchen, marble countertops, new stainless steel appliances, high speed internet, gleaming hardwood floors, queen size canopy beds, heavenly memory foam mattresses, 50' smart TV, all delivered with a Euro MCM flare! Blossom is ideal for a romantic getaway, smart business travel, or a quick City escape!

30 Jul – 6 Aug

₹9,835 per night

Guest favourite

Flat in Winchester

5.0 out of 5 average rating, 138 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.

28 Jun – 5 Jul

₹14,048 per night

Guest favourite

Flat in Winchester

4.98 out of 5 average rating, 217 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.

25 Jul – 1 Aug

₹9,579 per night

Guest favourite

Cottage in Winchester

4.9 out of 5 average rating, 99 reviews

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

13–20 Sep

₹7,746 per night

Guest favourite

Flat in Winchester

4.94 out of 5 average rating, 272 reviews

Downtown 1920's Gas Station

Luxury 1920’s Refurbished Gas Station repurposed into a beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.

16–23 Aug

₹12,911 per night

Guest favourite

Flat in Winchester

4.8 out of 5 average rating, 287 reviews

Pretty Little Apt by the Train II

This little place is just plain charming. Lots of light and personality. Wonderful alternative to the typical hotel experience. Fabulous for short term rental needs. Come enjoy Downtown Flat screen TV/ Record Player FREE PARKING/WIFI Near Piccadillys Pub, the Walking Mall, our beautiful and historic library, Shenandoah Univ. -5 minute Winchester Med Center -5 min DC. -1.5 hr Skyline Drive -30 min Free Parking too ! Reach out on social media if you need more. Michele Bouve Hoffman

27 Nov – 4 Dec

₹8,611 per night

Guest favourite

Home in Winchester

4.97 out of 5 average rating, 213 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.

24 Nov – 1 Dec

₹10,248 per night

Guest favourite

Cottage in Winchester

4.97 out of 5 average rating, 424 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

20–27 Jan

₹10,450 per night

Guest favourite

Guest suite in Winchester

4.79 out of 5 average rating, 278 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.

8–15 Jul

₹6,167 per night

Guest favourite

Townhouse in Winchester

4.95 out of 5 average rating, 171 reviews

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.

15–22 Dec

₹9,572 per night