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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.

Adorable one bedroom guest cabin in the woods
SUPERHOST
Entire guesthouse · 4 guests · 3 beds · 1 bath
Adorable one bedroom guest cabin in the woodsTake a break and unwind at this peaceful oasis located on 15 acres of piney woods 10 minutes from La Grange, 20 minutes from Round Top, and 5 minutes from the quaint town of Winchester.
SMITHVILLE GUEST HAUS
SUPERHOST
Entire guesthouse · 4 guests · 3 beds · 1 bath
SMITHVILLE GUEST HAUSWelcome to Smithville Guest Haus in Small Town USA! Only 1 block from Main Street featuring shops, restaurants and night life. Close to Round Top/Warrenton, Austin and Circuit of Americas. Take a stroll in town or spend a day in the country seeking out a treasured antique. However you choose to spend your day, know that you will RELAX IN COMFORT at Smithville Guest Haus. We can't wait to have you as our guest(s)! Health and safety are a priority for our guests!! Your hosts, Rob and Sharon
Best Little Cabin in Texas
SUPERHOST
Entire cabin · 4 guests · 2 beds · 2 baths
Best Little Cabin in TexasSecluded cabin on 200 acres of private pine forest. Enjoy hiking & views from large deck. Cabin's decor based on local legend & Broadway hit, The Best Little Whorehouse in Texas, replete with the madam's bed. Fully stocked kitchen with coffee maker, microwave, & dishwasher. BBQ on the outdoor propane grill and enjoy a campfire under the stars (bring your own firewood). 2 miles off highway. Pets OK with single $25 pet fee per stay. Up to three. Please let us know if you’ll be bringing yours.

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Other great vacation rentals in Winchester

  1. Entire residential home
  2. Smithville
The Little House on Nink
$150 per night
  1. Farm stay
  2. La Grange
Barn Bungalow near Round Top & La Grange
$150 per night
SUPERHOST
  1. Entire residential home
  2. Smithville
The Station! A fun space in the heart of downtown!
$130 per night
SUPERHOST
  1. Barn
  2. La Grange
Steelwaters. Contemporary Quonset on forty acres.
$150 per night
SUPERHOST
  1. Entire guesthouse
  2. Smithville
Cottage w/ Pool in Historic Downtown
$86 per night
SUPERHOST
  1. Entire guesthouse
  2. Smithville
Red Rooster Barn
$77 per night
SUPERHOST
  1. Entire residential home
  2. La Grange
#110 - 20 min to Round Top Antique Week
$143 per night
SUPERHOST
  1. Entire cabin
  2. La Grange
Clean cabin in woods w/ Wifi, nature, views, peace
$189 per night
  1. Entire residential home
  2. La Grange
Elegant, “Chandelier Bungalow” in La Grange!
$225 per night
SUPERHOST
  1. Entire cabin
  2. La Grange
Piney Woods Cabin
$185 per night
  1. Entire residential home
  2. Smithville
Ruby's Foxcroft Cottage - Smithville, Texas
$205 per night
SUPERHOST
  1. Entire bungalow
  2. La Grange
✨Funky Old Farmhouse✨ Walk to Shop, Dine, & Drink
$196 per night