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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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

Sugar Shack, a retro studio apartment
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Sugar Shack, a retro studio apartmentIn this unique space you get to enjoy some of the new with the old. Building is over 150 years old. Original hardwood floors beautifully sanded, stained and restored. 7’ tall replacement windows allow lots of natural light & air to flow through. 10’ ceilings in main part of studio adds spaciousness. 8’ bar attached to exposed brick wall offers a place to dine as well as provides a workspace. Newly constructed kitchen & bath with stackable washer/dryer. Comfort & style throughout! We welcome you!
The Primrose inside historic commercial bldg
SUPERHOST
Entire rental unit · 5 guests · 4 beds · 1 bath
The Primrose inside historic commercial bldgComfy 2 bedroom, 1 bath 2nd story apartment located on town square in Winchester. Apartment has 2 Bedrooms. Master Bedroom has a Queen bed. Second Bedroom has 3 twin beds. One Bath with tub/shower combo. Must walk through Master Bedroom to access Bathroom. KIT open to LR w/all appls & everything you need to cook at home. Living Room with leather reclining sofa and massage chair to enjoy. Wifi, 48” TV w/Firestick & street side parking. Gas grill available on back stairs fire escape landing.
Container Home GREAT Countryside Views COZY Stay
SUPERHOST
Entire cabin · 4 guests · 1 bed · 1 bath
Container Home GREAT Countryside Views COZY StaySinging Hills Cabin is the ultimate getaway for fresh air and an unbeatable view of the countryside. Enjoy morning coffee as the sun rises from the large front porch. This newly renovated container home is perfect for small families looking for an outdoor escape or for couples seeking a romantic getaway. It is located on a 40 acre hobby farm, so do not be surprised if you see cows and other wildlife during your stay! The best deer hunting, river access, and restaurants are located minutes away.

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Other great vacation rentals in Winchester

SUPERHOST
  1. Entire cabin
  2. Jacksonville
Audrey's Abode
$119 per night
SUPERHOST
  1. Entire guest suite
  2. Pittsfield
Florence Guest House--Loft Unit
$30 per night
SUPERHOST
  1. Entire rental unit
  2. Jacksonville
Ayers Mansion II Suite F - DeWolf Extended Suites
$81 per night
SUPERHOST
  1. Entire cottage
  2. Murrayville
Peace on the Prairie Too - Tiny House
$95 per night
SUPERHOST
  1. Entire rental unit
  2. Murrayville
Peace on the Prairie - Studio Apartment
$75 per night
  1. Entire cottage
  2. Pearl
Beautiful Secluded Home With a breathtaking view
$150 per night
SUPERHOST
  1. Entire rental unit
  2. Jacksonville
Ayers Mansion II Suite E - DeWolf Extended Suites
$91 per night
SUPERHOST
  1. Entire residential home
  2. Pittsfield
Enjoy the warmth of a home
$78 per night
SUPERHOST
  1. Tiny house
  2. Mount Sterling
Tiny Treasure
$80 per night
SUPERHOST
  1. Entire rental unit
  2. Carrollton
Farmhouse Loft
$75 per night
SUPERHOST
  1. Entire loft
  2. Virginia
Two Doors Down Loft, Virginia-Lincoln territory!
$65 per night
SUPERHOST
  1. Entire rental unit
  2. Jacksonville
Ayers Mansion II Suite B - DeWolf Extended Suites
$104 per night