Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester

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

Guest favourite

Apartment in Winchester

4.89 out of 5 average rating, 101 reviews

Modern Twist in Old Town! Rock n' Roll FUN!

Basil is your personal, 2 bedroom, Uber-stylish apartment, located in downtown Winchester with private parking! New & sparkling clean, enjoy high end finishes & creative design! Enjoy hot showers in the marble bath, sink into the shearling-covered couch relaxing in front of the new 55' smart TV, catch up with work in your private office, then walk to a great happy hour & dinner downtown! End your day cozying up in one of the two queen size, memory foam canopy beds! Basil is your perfect Airbnb!

Aug. 21 – 28

$218 CAD per night
Guest favourite

Home in Winchester

4.97 out of 5 average rating, 163 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 !

Jan. 2 – 9

$244 CAD per night
Guest favourite

Apartment in Winchester

5.0 out of 5 average rating, 134 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.

Sep. 14 – 21

$243 CAD per night

Popular amenities for Winchester vacation rentals

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
Museum of the Shenandoah Valley72 locals recommend
Shenandoah Valley Discovery Museum34 locals recommend

Other great vacation rentals in Winchester

Guest favourite

Cottage in Shepherdstown

4.96 out of 5 average rating, 176 reviews

The GW Hollida Cottage of Shepherdstown

Sep. 6 – 13

$183 CAD per night
Guest favourite

Farm stay in Romney

4.98 out of 5 average rating, 281 reviews

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

Jun. 2 – 9

$204 CAD per night
Guest favourite

Guest suite in Summit Point

4.97 out of 5 average rating, 126 reviews

The Big Room - Historic Schoolhouse

Mar. 9 – 16

$203 CAD per night
Guest favourite

Loft in Purcellville

4.99 out of 5 average rating, 284 reviews

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Nov. 22 – 29

$185 CAD per night
Guest favourite

Cabin in Augusta ( Capon Bridge)

4.96 out of 5 average rating, 129 reviews

Nirvana, Mountain View

Dec. 30 – Jan. 6

$107 CAD per night
Guest favourite

Apartment in Winchester

4.96 out of 5 average rating, 45 reviews

Newly repurposed Historic Home in Winchester VA!

Aug. 14 – 21

$157 CAD per night
Guest favourite

Apartment in Winchester

4.97 out of 5 average rating, 75 reviews

Historic Wisteria House on Old Town Walking Mall

Jun. 1 – 8

$206 CAD per night
Guest favourite

Cottage in Winchester

4.89 out of 5 average rating, 95 reviews

Lockley Cottage at Historic Perry Farm

Sep. 14 – 21

$133 CAD per night
Guest favourite

Place to stay in Winchester

4.86 out of 5 average rating, 35 reviews

Crash Landing

Mar. 10 – 17

$106 CAD per night
Guest favourite

Townhouse in Winchester

4.92 out of 5 average rating, 36 reviews

Brewhouse renovated row house steps from downtown

Mar. 20 – 27

$243 CAD per night
Guest favourite

Guest suite in Winchester

4.92 out of 5 average rating, 51 reviews

Retro Vibe Studio

Jun. 5 – 12

$151 CAD per night
Guest favourite

Home in Winchester

4.91 out of 5 average rating, 23 reviews

Misty Meadow has quite setting in the country.

May 21 – 28

$142 CAD per night

Quick stats about vacation rentals in Winchester

Total rentals

90 properties

Wifi availability

90 properties include access to wifi

Rentals with dedicated workspaces

60 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

5.7K reviews

Destinations to explore

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  2. United States
  3. Virginia
  4. Winchester