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.

Guest favorite

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 20 – 27

G$26,799 GYD per night
Guest favorite

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 !

Dec 31 – Jan 7

G$31,054 GYD per night
Guest favorite

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.

Aug 6 – 13

G$31,159 GYD 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 favorite

Cottage in Woodstock

4.98 out of 5 average rating, 172 reviews

Cottage on Boxwood Lane

Jul 14 – 21

G$18,144 GYD per night
Guest favorite

Tiny home in Linville

4.99 out of 5 average rating, 593 reviews

The spring house at Thistle Hollow

Jul 25 – Aug 1

G$24,417 GYD per night
Guest favorite

Loft in Purcellville

4.99 out of 5 average rating, 284 reviews

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Nov 18 – 25

G$23,125 GYD per night
Guest favorite

Farm stay in Romney

4.98 out of 5 average rating, 281 reviews

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

Jul 22 – 29

G$27,508 GYD per night
Guest favorite

Cabin in Augusta ( Capon Bridge)

4.96 out of 5 average rating, 129 reviews

Nirvana, Mountain View

Nov 12 – 19

G$13,357 GYD per night
Guest favorite

Guest suite in Shepherdstown

4.96 out of 5 average rating, 563 reviews

Historic Scrabble, Shepherdstown

Jun 27 – Jul 4

G$19,482 GYD per night
Guest favorite

Guest suite in Summit Point

4.97 out of 5 average rating, 126 reviews

The Big Room - Historic Schoolhouse

Feb 11 – 18

G$26,892 GYD per night
Guest favorite

Apartment in Woodstock

4.88 out of 5 average rating, 468 reviews

Heart of Town-Pet Friendly

Nov 2 – 9

G$18,484 GYD per night
Guest favorite

Guesthouse in Round Hill

4.98 out of 5 average rating, 371 reviews

Private Carriage House

May 20 – 27

G$27,493 GYD per night
Guest favorite

Bungalow in Great Cacapon

4.9 out of 5 average rating, 460 reviews

Rooster Wrest in the Trees

Feb 28 – Mar 7

G$20,714 GYD per night
Guest favorite

Guest suite in Smithsburg

4.99 out of 5 average rating, 146 reviews

Creekside Retreat at the Jewel Vinsota

Sep 17 – 24

G$18,107 GYD per night
Guest favorite

Earthen home in Broadway

4.99 out of 5 average rating, 627 reviews

Hobbit Style Underground Cabin

Mar 14 – 21

G$35,825 GYD per night

Other great vacation rentals in Winchester

Guest favorite

Apartment in Winchester

4.96 out of 5 average rating, 45 reviews

Newly repurposed Historic Home in Winchester VA!

Jul 14 – 21

G$20,272 GYD per night
Guest favorite

Apartment in Winchester

4.97 out of 5 average rating, 75 reviews

Historic Wisteria House on Old Town Walking Mall

Aug 12 – 19

G$27,066 GYD per night
Guest favorite

Cottage in Winchester

4.89 out of 5 average rating, 94 reviews

Lockley Cottage at Historic Perry Farm

Sep 7 – 14

G$18,657 GYD per night
Guest favorite

Townhouse in Winchester

4.92 out of 5 average rating, 36 reviews

Brewhouse renovated row house steps from downtown

Feb 6 – 13

G$30,594 GYD per night
Guest favorite

Place to stay in Winchester

4.86 out of 5 average rating, 35 reviews

Crash Landing

Dec 7 – 14

G$14,046 GYD per night
Guest favorite

Guest suite in Winchester

4.92 out of 5 average rating, 51 reviews

Retro Vibe Studio

Jul 20 – 27

G$19,869 GYD per night
Guest favorite

Home in Winchester

4.91 out of 5 average rating, 23 reviews

Misty Meadow has quite setting in the country.

May 17 – 24

G$16,860 GYD per night
Superhost

Barn in Berryville

4.8 out of 5 average rating, 82 reviews

Modern House Barn on 66 acre Horse Farm

Jun 15 – 22

G$23,522 GYD per night
Guest favorite

Condo in Winchester

4.98 out of 5 average rating, 47 reviews

Historic District Downtown Winchester

Aug 24 – 31

G$35,338 GYD per night
Guest favorite

Guest suite in Clear Brook

5.0 out of 5 average rating, 37 reviews

Bluebird Bungalow

Apr 30 – May 7

G$21,807 GYD per night
Guest favorite

Home in Winchester

4.9 out of 5 average rating, 10 reviews

Cabin in Historic Old Town Winchester

Jun 4 – 11

G$30,427 GYD per night
Guest favorite

Home in Middletown

4.86 out of 5 average rating, 29 reviews

Mountain View Moto Retreat

Jun 3 – 10

G$21,135 GYD 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

Frequently Asked Questions

  • Are there apartment rentals with a dedicated workspace in Winchester?

    Yes! Work meets play with ease at over 30 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 house rentals in Winchester have self check-in?

    Absolutely! We offer over 10 house 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 20 homes with self check-in, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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