Vacation rentals in Winchester

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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, 165 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 !

Aug 2 – 9

G$26,735 GYD per night

Guest favorite

Apartment in Winchester

4.87 out of 5 average rating, 153 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!

Sep 3 – 10

G$24,797 GYD per night

Guest favorite

Apartment in Winchester

5.0 out of 5 average rating, 137 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.

Aug 19 – 26

G$34,499 GYD per night

Guest favorite

Apartment in Winchester

4.98 out of 5 average rating, 216 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.

Sep 25 – Oct 2

G$23,535 GYD per night

Guest favorite

Apartment in Winchester

4.94 out of 5 average rating, 270 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.

Jul 16 – 23

G$29,327 GYD per night

Guest favorite

Home in Inwood

4.89 out of 5 average rating, 545 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.

Oct 7 – 14

G$17,879 GYD 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

Sep 22 – 29

G$21,146 GYD per night

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 212 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.

Jul 30 – Aug 6

G$25,260 GYD per night

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 421 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.

Dec 28 – Jan 4

G$25,647 GYD per night

Guest favorite

Cabin in Lost River

4.95 out of 5 average rating, 111 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!

Jan 14 – 21

G$20,235 GYD per night

Guest favorite

Guest suite in Winchester

4.79 out of 5 average rating, 277 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.

Feb 7 – 14

G$20,518 GYD per night

Guest favorite

Townhouse in Winchester

4.95 out of 5 average rating, 170 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.

Aug 4 – 11

G$20,017 GYD 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

Costco Wholesale3 locals recommend

Walmart Supercenter4 locals recommend

Apple Blossom Mall station14 locals recommend

Shenandoah Valley Discovery Museum34 locals recommend

Museum of the Shenandoah Valley72 locals recommend

Other great vacation rentals in Winchester

Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 181 reviews

The GW Hollida Cottage of Shepherdstown

Mar 26 – Apr 2

G$25,285 GYD per night

Guest favorite

Cabin in Augusta ( Capon Bridge)

4.96 out of 5 average rating, 131 reviews

Nirvana, Mountain View

Sep 26 – Oct 3

G$13,322 GYD per night

Guest favorite

Farm stay in Romney

4.98 out of 5 average rating, 285 reviews

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

Oct 1 – 8

G$28,783 GYD per night

Guest favorite

Loft in Purcellville

4.99 out of 5 average rating, 286 reviews

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Dec 19 – 26

G$22,603 GYD per night

Guest favorite

Guest suite in Summit Point

4.97 out of 5 average rating, 128 reviews

The Big Room - Historic Schoolhouse

Sep 23 – 30

G$26,616 GYD per night

Guest favorite

Tiny home in Linville

4.99 out of 5 average rating, 600 reviews

The spring house at Thistle Hollow

Aug 15 – 22

G$24,236 GYD per night

Guest favorite

Guest suite in Shepherdstown

4.96 out of 5 average rating, 565 reviews

Historic Scrabble, Shepherdstown

Aug 23 – 30

G$17,614 GYD per night

Superhost

Home in Strasburg

4.89 out of 5 average rating, 228 reviews

Shenandoah Siesta

Jun 19 – 26

G$30,473 GYD per night

Show all

Other great vacation rentals in Winchester

Guest favorite

Townhouse in Winchester

4.93 out of 5 average rating, 40 reviews

Brewhouse renovated row house steps from downtown

Jan 21 – 28

G$30,513 GYD per night

Guest favorite

Place to stay in Winchester

4.86 out of 5 average rating, 44 reviews

Crash Landing

Nov 13 – 20

G$14,008 GYD per night

Guest favorite

Condo in Winchester

4.98 out of 5 average rating, 49 reviews

Historic District Downtown Winchester

Oct 26 – Nov 2

G$32,482 GYD per night

Guest favorite

Guest suite in Winchester

4.92 out of 5 average rating, 51 reviews

Retro Vibe Studio

Jun 4 – 11

G$19,510 GYD per night

Superhost

Apartment in Winchester

5.0 out of 5 average rating, 5 reviews

Cameron Loft 2 Story Studio with 1.5 Bath Downtown

Aug 17 – 24

G$22,928 GYD per night

Superhost

Barn in Berryville

4.8 out of 5 average rating, 84 reviews

Modern House Barn on 66 acre Horse Farm

Jul 14 – 21

G$22,969 GYD per night

Guest favorite

Home in Winchester

4.9 out of 5 average rating, 10 reviews

Cabin in Historic Old Town Winchester

Oct 1 – 8

G$30,408 GYD per night

Guest favorite

Home in Winchester

4.92 out of 5 average rating, 24 reviews

Misty Meadow has quite setting in the country.

Jun 24 – Jul 1

G$17,995 GYD 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 apartment rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 20 apartment 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 house rentals in Winchester have wifi?
Absolutely! We offer over 30 house 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 House Rentals in Winchester?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with self check-in, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Winchester

Top-rated vacation rentals in Winchester

Vacation rentals for every style

Cottages

Cabins

Apartments

Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Other great vacation rentals in Winchester

Cottage in Shepherdstown

Cabin in Augusta ( Capon Bridge)

Farm stay in Romney

Loft in Purcellville

Guest suite in Summit Point

Tiny home in Linville

Guest suite in Shepherdstown

Home in Strasburg

Other great vacation rentals in Winchester

Townhouse in Winchester

Place to stay in Winchester

Condo in Winchester

Guest suite in Winchester

Apartment in Winchester

Barn in Berryville

Home in Winchester

Home 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 apartment rentals with a dedicated workspace in Winchester?

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

Do house 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 House Rentals in Winchester?

Destinations to explore