Holiday rentals in Winchester

Cottage w/ Pool in Historic Downtown

Smithville is a quaint, thriving city with a very relaxing feel. It has numerous outdoor activities within 30 minutes if you enjoy hiking, canoe/kayaking, biking, fishing, etc. The cottage is within walking distance to downtown restaurants and shops. The town offers many great boutiques and antique stores. The cottage is a block from famous homes featured in the movies, Hope Floats and The Tree of Life. You can see the Hope Floats house from the porch! Come unwind and enjoy the small-town life!

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

Bishop Carriage House

Your own cozy hide away in historic downtown Smithville, Texas. Private parking and balcony that is on local parade route, where you can enjoy the cool evenings. Complete kitchen with, full size frig and stove and all you will need to cook a meal. Great restaurants and shops within walking distance. Queen size bed and a full size sofa pull-out with upgraded mattress. WiFi and work space. Let’s not forget a coffee station. We do allow pets, but there is a pet fee. Please included at reservation.

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.

The Hobbit's Nest

Escape to a world of magic and wonder with a visit to the enchanting Hobbit's Nest treehouse. Whether you seek a romantic getaway or a fun-filled family vacation, this unique glamping experience offers the serenity of nature with all the comforts of home. Resting amidst the lush treetops of Lost Pines Forest, the Hobbit's Nest promises an unforgettable stay where your imagination can run wild and your soul can find solace in the beauty of the natural world in the 42 acre Lost Pines Shire.

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.

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.

Relaxing Ranch, Friendly Animals, Modern Stay

Unwind in this modern cabin where nature meets comfort. Enjoy an interactive experience with friendly farm animals eager for pets and treats. Soak in views of the serene pond, grazing cows, and horses. Explore trails on secluded acreage. Light-filtering blinds, AC, and Starlink WiFi. Built in 2023. 7/7/25 update. We have piglets, baby goats, and calves right now until end of August. Close to Circuit of the Americas, Bastrop, Austin Airport, and Smithville.

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.