Winchester vacation rentals

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Top-rated vacation rentals in Winchester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

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 !

Nov 5 – 12

R2,436 ZAR per night

Guest favorite

Apartment 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!

Aug 24 – 31

R2,240 ZAR per night

Guest favorite

Apartment 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.

Jul 31 – Aug 7

R3,144 ZAR per night

Guest favorite

Apartment 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.

Aug 24 – 31

R2,145 ZAR per night

Guest favorite

Apartment 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.

Aug 16 – 23

R2,890 ZAR per night

Guest favorite

Home in Inwood

4.89 out of 5 average rating, 549 reviews

Arden House, Inwood WV

Ground level studio apartment. No steps. Completely separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed and sofa. In a separate living area, there is a queen bed, TV, private bath, desk, table, microwave, convection oven, air fryer, refrigerator 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.

Dec 13 – 20

R1,629 ZAR per night

Guest favorite

Apartment 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

Apr 19 – 26

R1,927 ZAR per night

Guest favorite

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.

Jan 21 – 28

R2,014 ZAR per night

Guest favorite

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.

Apr 11 – 18

R2,337 ZAR 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!

Feb 10 – 17

R1,844 ZAR per night

Guest favorite

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.

Nov 28 – Dec 5

R1,824 ZAR per night

Guest favorite

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.

Dec 16 – 23

R2,142 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winchester vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Winchester's top sights

Old Town Winchester25 locals recommend

Shenandoah Valley Discovery Museum34 locals recommend

Costco Wholesale3 locals recommend

Walmart Supercenter4 locals recommend

Apple Blossom Mall station14 locals recommend

Museum of the Shenandoah Valley72 locals recommend

Other great vacation rentals in Winchester

Guest favorite

Farm stay in Romney

4.98 out of 5 average rating, 287 reviews

Potomac Hills B&B on 15 Acre Farm with a View

Sep 4 – 11

R2,606 ZAR per night

Guest favorite

Farm stay in Round Hill

4.94 out of 5 average rating, 347 reviews

Come and get your goat on!

Sep 4 – 11

R2,351 ZAR per night

Guest favorite

Loft in Purcellville

4.99 out of 5 average rating, 289 reviews

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Dec 4 – 11

R2,099 ZAR per night

Guest favorite

Cabin in Augusta ( Capon Bridge)

4.96 out of 5 average rating, 131 reviews

Nirvana, Mountain View

Jan 21 – 28

R1,214 ZAR per night

Guest favorite

Home in Edinburg

4.98 out of 5 average rating, 355 reviews

Jay Birds Nest - Pet Friendly

Sep 12 – 19

R2,035 ZAR per night

Guest favorite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 567 reviews

Historic Scrabble, Shepherdstown

Sep 3 – 10

R1,605 ZAR per night

Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 182 reviews

The GW Hollida Cottage of Shepherdstown

Apr 12 – 19

R2,304 ZAR per night

Guest favorite

Cabin in Lost City

4.97 out of 5 average rating, 250 reviews

High View Hideaway - A Cozy Lost River Cabin

Jun 14 – 21

R2,009 ZAR per night

Show all

Other great vacation rentals in Winchester

Guest favorite

Apartment in Winchester

4.94 out of 5 average rating, 50 reviews

Newly repurposed Historic Home in Winchester VA!

Jul 30 – Aug 6

R2,025 ZAR per night

Guest favorite

Apartment in Winchester

4.97 out of 5 average rating, 77 reviews

Historic Wisteria House on Old Town Walking Mall

Aug 22 – 29

R2,409 ZAR per night

Guest favorite

Place to stay in Winchester

4.87 out of 5 average rating, 46 reviews

Crash Landing

Nov 10 – 17

R1,277 ZAR per night

Guest favorite

Cottage in Winchester

4.9 out of 5 average rating, 99 reviews

Lockley Cottage at Historic Perry Farm

Sep 14 – 21

R1,735 ZAR per night

Guest favorite

Townhouse in Winchester

4.93 out of 5 average rating, 40 reviews

Brewhouse renovated row house steps from downtown

Aug 20 – 27

R2,780 ZAR per night

Guest favorite

Home in Winchester

4.91 out of 5 average rating, 11 reviews

Cabin in Historic Old Town Winchester

Aug 5 – 12

R2,749 ZAR per night

Guest favorite

Apartment in Winchester

5.0 out of 5 average rating, 11 reviews

Cameron Corner: King Bed & Office Downtown

Jun 28 – Jul 5

R2,488 ZAR per night

Guest favorite

Condo in Winchester

4.98 out of 5 average rating, 50 reviews

Historic District Downtown Winchester

Jul 8 – 15

R3,086 ZAR per night

Show all

Quick stats about vacation rentals in Winchester

Total rentals
90 properties
Wifi availability
90 properties include access to wifi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
6K reviews

Frequently Asked Questions

Are there house rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 20 house rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Winchester?
Experience the best of Winchester with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Winchester have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Winchester. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winchester have self check-in?
Absolutely! We offer over 20 apartment rentals with self check-in in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly apartment rentals in Winchester?
Four-legged friends are welcome in Winchester. Choose from more than 10 apartment rentals for guests traveling with pets.
What are the most popular amenities for Apartment Rentals in Winchester?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with wifi, over 20 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Winchester vacation rentals

Top-rated vacation rentals in Winchester

Vacation rentals for every style

Cabins

Apartments

Cottages

Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Other great vacation rentals in Winchester

Farm stay in Romney

Farm stay in Round Hill

Loft in Purcellville

Cabin in Augusta ( Capon Bridge)

Home in Edinburg

Guest suite in Shepherdstown

Cottage in Shepherdstown

Cabin in Lost City

Other great vacation rentals in Winchester

Apartment in Winchester

Apartment in Winchester

Place to stay in Winchester

Cottage in Winchester

Townhouse in Winchester

Home in Winchester

Apartment in Winchester

Condo in Winchester

Quick stats about vacation rentals in Winchester

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there house rentals with a dedicated workspace in Winchester?

How much does it cost to stay in apartment rentals in Winchester?

Do apartment rentals in Winchester have wifi?

Do apartment rentals in Winchester have self check-in?

Are there pet-friendly apartment rentals in Winchester?

What are the most popular amenities for Apartment Rentals in Winchester?

Destinations to explore