Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite
Two deer graze near a tranquil pond, with lush greenery surrounding the area. A wooden deck is visible in the foreground, featuring a covered seating area. In the background, a deer is seen near a feeder positioned by the water's edge.
Cabin in La Grange
4.98 out of 5 average rating, 182 reviews

Angeltom Cabin:20 AcreWoods >16+hot tub+tree house

A home nestled within 20 acres of pure pine forest. Two stock ponds & a tree house + playground + hot tub + UTV+ RV ! Upon arrival, you will be greeted with a country-style rustic cabin for 8 & RV for 8 , > 16 guests! She - shed with jacuzzi/spa for 5 . Eclectic stuff surrounding it ! 12 miles N. of La Grange; 90 min. away from Houston, Austin, or San Antonio. 25 min.away fromRound Top Antique Show Close enough to the city, yet private & peaceful. Enjoy a slice of country life & nature!

Top guest favorite
A cottage exterior is presented with a welcoming porch featuring two metal chairs and a small round table. A star decoration is mounted on the wall beside the door. Lush greenery surrounds the area, enhancing the inviting entrance.
Guesthouse in Smithville
4.94 out of 5 average rating, 337 reviews

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!

Top guest favorite
A spacious room features a large bed with neutral bedding and decorative pillows, accompanied by a vintage wooden table and chairs. A comfortable seating area includes a white chair and small table, while large windows provide natural light, framed with light curtains.
Guesthouse in Smithville
4.98 out of 5 average rating, 462 reviews

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

Top guest favorite
A serene pond reflects the surrounding trees and the home, creating a peaceful atmosphere. Lush greenery and open space are present on the property, complemented by a clear blue sky above.
Home in Smithville
4.96 out of 5 average rating, 195 reviews

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.

Top guest favorite
A charming treehouse constructed from natural materials is nestled among lush greenery. Its distinctive round windows and unique entrance door are highlighted, while a wooden bridge connects it to the surrounding landscape. The sky overhead is partly cloudy, adding to the enchanting ambiance.
Treehouse in Paige
4.94 out of 5 average rating, 119 reviews

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.

Top guest favorite
A charming cottage features a sturdy wooden door framed by large glass windows. The surrounding landscape includes well-maintained mulch beds with ornamental plants and a stone pathway leading to the entrance, while trees provide a natural backdrop.
Cottage in Smithville
5 out of 5 average rating, 139 reviews

Domovina Ranch Cottages ("The FW")

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.

Guest favorite
A firepit area is surrounded by multiple red Adirondack chairs, providing a cozy space for relaxation. Lush green grass frames the setting, with a large lap pool visible in the background, and a tree-lined landscape adds natural beauty.
Cottage in Brenham
4.96 out of 5 average rating, 187 reviews

★ Pool, HotTub- Cardinal Cottage, RoundTop/Brenham

-Private home & large lap pool for your use during your stay. No other renters on the property. -Wide open outdoor spaces to get away. A breath of fresh air. See the stars at night! -GREAT WiFi signal. - 1600 sq ft home on 11 acres. Common areas downstairs, bedrooms upstairs. -Lap Pool (not heated) and spa hot tub (heated year round). Pool towels provided. -Firepit area. I provide firewood, fire starters, & lighter. -Brenham 10 minute drive. Round Top 20 minute drive. Sorry, no pets.

Top guest favorite
The rustic cabin is enclosed by tall pine trees, showcasing a wooden exterior. A small porch is accessed by steps, featuring two red rocking chairs. An American flag hangs visibly, and a satellite dish is mounted on the roof under a clear sky.
Cabin in Smithville
4.93 out of 5 average rating, 270 reviews

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.

Top guest favorite
The exterior of a newly built modern cabin is featured, showcasing a wooden facade and a welcoming front porch. Large windows provide natural light, while steps lead up to the entrance. Surrounding trees and a landscaped yard enhance the serene outdoor setting.
Home in La Grange
4.99 out of 5 average rating, 136 reviews

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.

Guest favorite
A cozy studio space is shown, featuring a comfortable seating area with a dark sofa and a light coffee table. The kitchen is equipped with an oven and small appliances, while wooden accents and wall art add warmth. A small dining table and chairs are also visible.
Apartment in Smithville
4.9 out of 5 average rating, 358 reviews

Bishop Carriage House

Your own cozy upstairs 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 queen size sofa pull-out with upgraded mattress. WiFi and work space. We do allow pets, but there is a pet fee. Please included at reservation.

Top guest favorite
A modern open-concept cabin space features a spacious bed with crisp white linens. Natural light filters through large windows, revealing views of the surrounding trees. A kitchen area includes bar stools and a microwave, offering a warm, inviting setting amidst nature.
Farm stay in Cedar Creek
4.96 out of 5 average rating, 155 reviews

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.

Top guest favorite
A quaint cottage with a welcoming front porch is surrounded by natural greenery and landscaped paths. The entrance features a red door and light-colored siding, providing a charming contrast to the outdoor space with scattered stones and plants.
Farm stay in Paige
4.99 out of 5 average rating, 181 reviews

Shady Paddock Farm-Willow House

Welcome to our little country farm! Escape the city life for a romantic get away or just some much needed down time. Willow House is privately nestled among the trees in our back paddock, allowing views of the lovely country side from the living area as well as the cozy front porch. There is also a picnic table and charcoal grill for your use.

Popular amenities for Winchester vacation rentals

  1. Airbnb
  2. United States
  3. Texas
  4. Fayette County
  5. Winchester