Vacation rentals in Winchester

Pasture Bedtime Retreat

Welcome to Pasture Bedtime Retreat, your cozy, eclectic cottage nestled perfectly in between La Grange (6 mins), Round Top (10 mins), and Fayetteville (13 mins). This charming guest house offers a unique blend of homely comfort, artistic flair, and modern amenities, including high-speed fiber internet, a smart TV, a Keurig coffee maker, a mini-fridge, and a microwave. After a day of treasure hunting, enjoy the view of grazing cows, challenge someone to ping-pong, and relax in the outdoor space!

The Rustic Retreat | 25 Acres | Cedar Cabin

Its 15 mins. to Round Top & 9 min. to La Grange. Designed for families or couples looking to relax and unplug, this quintessential La Grange cabin boasts the utmost privacy and serenity on your getaway. Once you've settled in, explore the property where you can find a serene pond, wildlife, and livestock grazing. Gather around the fire pit for s’mores and stories under the stars by night. This cabin is perfectly located near wineries & nature parks while still maintaining its remote feeling.

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 Treehouse

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.

Best Little Cabin in Texas

Secluded cabin on 250 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 $30 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.

Piney Creek Cabin

Take a break and unwind at this peaceful oasis. Enjoy the private, quiet, peaceful cabin tucked back in the woods. Eight hundred sq ft of beautiful living space with 2 Bedrooms and 2 Full Bathrooms and a Loft. The porch is a great place to relax and take in the Beauty around you. The view from the cozy cabin is a stocked lake and dock. Fish, kayak, play basketball, enjoy a walk, The possibilities are endless. Abundant Wildlife can be found all over the property.

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. We have piggies, mini goats, cows, horses, donkeys, and a black lab to say hello to 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.

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.

Piney Woods Cabin on 20 Acres/Close to Round Top

Previously 4.99 ⭐️ with over 300 reviews⭐️ Cabin set among 20 acres of pine forest makes a great getaway. Sit on the porch watch the deer at the feeder and relax among the quietest of nature or explore the 20 wooded acres. Full kitchen and decorator's touches. The cabin is close to Round Top, La Grange, and Smithville and minutes to locally famous Murphy's Steakhouse. Get away from it all!