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.
Apartment in Winchester
4.89 out of 5 average rating, 101 reviewsModern 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
Home in Winchester
4.97 out of 5 average rating, 163 reviewsCameron 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
Apartment in Winchester
5.0 out of 5 average rating, 134 reviewsOld 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Cottage in Woodstock
4.98 out of 5 average rating, 172 reviewsCottage on Boxwood Lane
Jul 14 – 21
Tiny home in Linville
4.99 out of 5 average rating, 593 reviewsThe spring house at Thistle Hollow
Jul 25 – Aug 1
Loft in Purcellville
4.99 out of 5 average rating, 284 reviews"When Pigs Fly" Airbnb Most Hospitable Host in VA
Nov 18 – 25
Farm stay in Romney
4.98 out of 5 average rating, 281 reviewsPotomac Hills B&B on 15 Acre Farm with a View
Jul 22 – 29
Cabin in Augusta ( Capon Bridge)
4.96 out of 5 average rating, 129 reviewsNirvana, Mountain View
Nov 12 – 19
Guest suite in Shepherdstown
4.96 out of 5 average rating, 563 reviewsHistoric Scrabble, Shepherdstown
Jun 27 – Jul 4
Guest suite in Summit Point
4.97 out of 5 average rating, 126 reviewsThe Big Room - Historic Schoolhouse
Feb 11 – 18
Apartment in Woodstock
4.88 out of 5 average rating, 468 reviewsHeart of Town-Pet Friendly
Nov 2 – 9
Guesthouse in Round Hill
4.98 out of 5 average rating, 371 reviewsPrivate Carriage House
May 20 – 27
Bungalow in Great Cacapon
4.9 out of 5 average rating, 460 reviewsRooster Wrest in the Trees
Feb 28 – Mar 7
Guest suite in Smithsburg
4.99 out of 5 average rating, 146 reviewsCreekside Retreat at the Jewel Vinsota
Sep 17 – 24
Earthen home in Broadway
4.99 out of 5 average rating, 627 reviewsHobbit Style Underground Cabin
Mar 14 – 21
Other great vacation rentals in Winchester
Apartment in Winchester
4.96 out of 5 average rating, 45 reviewsNewly repurposed Historic Home in Winchester VA!
Jul 14 – 21
Apartment in Winchester
4.97 out of 5 average rating, 75 reviewsHistoric Wisteria House on Old Town Walking Mall
Aug 12 – 19
Cottage in Winchester
4.89 out of 5 average rating, 94 reviewsLockley Cottage at Historic Perry Farm
Sep 7 – 14
Townhouse in Winchester
4.92 out of 5 average rating, 36 reviewsBrewhouse renovated row house steps from downtown
Feb 6 – 13
Place to stay in Winchester
4.86 out of 5 average rating, 35 reviewsCrash Landing
Dec 7 – 14
Guest suite in Winchester
4.92 out of 5 average rating, 51 reviewsRetro Vibe Studio
Jul 20 – 27
Home in Winchester
4.91 out of 5 average rating, 23 reviewsMisty Meadow has quite setting in the country.
May 17 – 24
Barn in Berryville
4.8 out of 5 average rating, 82 reviewsModern House Barn on 66 acre Horse Farm
Jun 15 – 22
Condo in Winchester
4.98 out of 5 average rating, 47 reviewsHistoric District Downtown Winchester
Aug 24 – 31
Guest suite in Clear Brook
5.0 out of 5 average rating, 37 reviewsBluebird Bungalow
Apr 30 – May 7
Home in Winchester
4.9 out of 5 average rating, 10 reviewsCabin in Historic Old Town Winchester
Jun 4 – 11
Home in Middletown
4.86 out of 5 average rating, 29 reviewsMountain View Moto Retreat
Jun 3 – 10
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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