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

Raymond's Tiny at “The Patch” 28+ acres w/ 2 ponds

The Patch-your private getaway on 28+ acres of Texas woodlands. This cozy 1bedroom+loft (2 beds total) 1 bath tiny home offers a peaceful, secluded with room for maximum of 3 guests. You'll be surrounded by wildlife,nature, just steps away from 2 beautiful ponds. Enjoy mornings on the porch, or stargaze at night. Unplug, hike, bird watch, or relax--The Patch offers a peaceful reset in the heart of nature-Texas style. No smoking/No Pets. This ensures an environment all guests are able to enjo

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.

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.

The Grange Country Cabin

Enjoy a stay in our country Texas cabin, surrounded by oak trees, pine trees, and just the sounds of nature. Sit on the porch and enjoy the sounds of the birds singing, or enjoy the use of the covered picnic and fire pit area. And speaking of birds, the binoculars are hanging behind the front door for your use. We have a running list of birds we have seen from the front porch. You can also enjoy our hiking trails throughout the property.

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.

La Grange Guesthouse with Pool

Lovely, comfortable guest house in a fabulous location near Round Top, Warrenton, Fayetteville, Smithville, Schulenburg and Flatonia. Ample parking, privacy and a pool to enjoy after a long day of shopping, cycling or hiking. Also includes access to a refrigerator and outdoor kitchen. You will have all of the necessities, plus little extras like Amazon Echo, smart TV and charging side tables.