Vacation rentals in Winchester

SMITHVILLE GUEST HAUS

Welcome 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

Emma’s-Peace and Quiet Texas Style—Pet Friendly

Emma’s at The Patch in Paige is a place where family and friends gather, memories are made, and Nature is right outside the door. A spacious outdoor deck is perfect for gathering or stargazing. Here the land stretches wide, and time seems to move a bit slower. Families love Emma’s spacious interior and well stocked kitchen. With open spaces, fishing pier, quiet trails, and room to stargaze-it’s the kind of place where you and your pet settle in quickly. It’s Nature’s sanctuary inviting you in

The Midnight Retreat | 22 Acres | Container Home

Located 15 mins. from Round Top & 9 mins. from La Grange. Perfect for a romantic escape or solo getaway from the city, this Texas vacation rental in the Prairie and Lakes region offers a no-frills destination with modern amenities. You’ll be surrounded by oak-filled woods, wildlife, and a star-filled night sky at this efficient 1-bed, 1-bath tiny home on 22 acres. Relax on the spacious patio and bask in the great outdoors. * Please note other home on property, 300ft away. * * Shared parking*

Private Fishing Spot, Family Fun & Wifi - 10 Acres

La Puerta Pink Casita invites you to come savor the quietness and beauty of the countryside in a fully furnished 2 bed/2 bath home. Spend time reminiscing, reconnecting and reenergizing with friends, family or dog(s) by the fire, making s'mores. Need wifi? We have Starlink wifi for checking email or Netflix. Enjoy 10 acres of land while sitting in the backyard. The summer heat did not dry the pond and the bass and catfish are thriving! Bring fishing poles and enjoy time by the pond.

Domovina Ranch Cottages ("The Hemingway")

We offer two beautiful cottages (The Hemingway and The FW) that are located on 50 acres at the end of a dead end road. Surrounded by thousands of privately owned acreage, featuring abundant wildlife (deer, turkey, birdwatchers paradise). This is a working cattle ranch so you can take in sunsets as cattle graze in front of you. Cottages are newly built and fully furnished. Lofts for reading, custom tile showers, outdoor fire pits and lounge area. Cottages are located away from main house.

Charming Texas Cottage - Main House

Escape to the heart of Texas and experience the charm of Smithville in our cozy cottage that sleeps up to 4 guests. Nestled on a double lot, this fenced property is perfect for guests traveling with their furry friends. With a queen bed and a full bed, our cottage is ideal for couples, families, or a group of friends looking for a relaxing getaway. We also have a 1 bedroom casita on the property that is completely fenced and private. Let us know if you're interested in both properties!

Best Little Cabin in Texas

Secluded 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 a $25 per pet fee. Up to three. Please let us know if you’ll be bringing yours.

The Modern Mule - Relaxing & stylish cabin escape!

Come getaway from the hustle and bustle of city life in this newly built modern cabin. 360 degree views of nature from every window and nestled away on over 10 acres, you and your guests will get the peace and quiet you’re looking for. Sit out on the deck and soak up the sun surrounded by an array of beautiful trees. Just minutes outside of La Grange where you will find charming shops, local eats and a perfect place to stay for The Ice Plant Bldg and Round Top Antique fair.

Paradise Pines

Private. Peaceful. Hugged by the forest. A romantic getaway or refuge from the city. Whether you are interested in soul searching, bird watching, skinny dipping, or exploring the many offerings of the local area, you will discover why it’s aptly named Paradise Pines. A well equipped kitchen and an outdoor grill will meet your needs. Swim in the heated pool underneath a canopy of pine trees and keep cool for an outdoor dining experience behind mosquito curtains.

Log Cabin Antique Week Retreat, serene lake

*New Stainless Steel Appliances!* Escape the stress of the city and experience the relaxing peace and tranquility of our log cabin surrounded by tall pines with stunning views of Lake Jean. Imagine the look on the faces of your friends or family when they step out of the car and take in the calm, smooth surface of the lake through the trees. They look at you and smile, wondering where you found this place. Inside you'll know that you made the right choice.

Pinehaven Luxury Glamping

Enjoy nature in a luxurious, climate controlled setting nestled in beautiful piney woods! Our safari tent is equipped with everything you need to relax and unwind. Take a bath in the claw foot tub, enjoy a book on the front porch, and sleep peacefully in the cozy king sized bed. Pinehaven will provide you an unforgettable glamping experience! Located approximately 20 minutes from Round Top, Texas.

The Station! Monthly rental- downtown Smithville!

Hi! My name is beckett and I’m so happy to share this space we have created, with you! I think you will have an amazing experience and come away refreshed and energized! It’s a 1920’s gas station building made into a fun space to hang out while experiencing this unique town. Have a blast in Smithville- a small town with a big heart! Warmest regards, -beckett 😊