Vacation rentals in Winchester

4.98 out of 5 average rating, 173 reviews

Cabin in La Grange

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!

4.95 out of 5 average rating, 328 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!

4.96 out of 5 average rating, 127 reviews

Farm stay in Cedar Creek

Modern stay on a Relaxing Ranch & Friendly animals

Unwind in this beautiful, modern cabin, where nature meets comfort. Surrounded by adorable animals eager for pets and treats. An interactive experience with our farm animals. Soak in the views of a tranquil pond, grazing cows, and horses on rolling acreage. Explore walking trails. The property is 100% secluded, and light-filtering blinds are on every window. Built in 2023. Starlink WiFi Feel a million miles away, yet close to: Circuit of the Americas, Bastrop, Austin, AUS Airport, Smithville

4.98 out of 5 average rating, 442 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

4.9 out of 5 average rating, 348 reviews

Apartment in Smithville

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.

4.96 out of 5 average rating, 181 reviews

Home in Smithville

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.

5 out of 5 average rating, 152 reviews

Cottage in Smithville

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.

4.92 out of 5 average rating, 261 reviews

Cabin in Smithville

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.

4.98 out of 5 average rating, 121 reviews

Home in La Grange

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.

5 out of 5 average rating, 130 reviews

Barn in La Grange

Steelwaters. Contemporary Quonset on forty acres.

Beautiful apartment located upstairs in Quonset barn with high ceilings, tall windows offering natural light. Large deck with Weber gas grill and seating to enjoy water features and Natural surroundings. It has a contemporary custom kitchen and bath with steam shower. Cozy living area with a queen sleeper and a nice size bedroom. Downstairs offers a large seating area, half bath, and full size washer and dryer. For warm summer nights, enjoy an outdoor shower.

4.94 out of 5 average rating, 228 reviews

Cabin in La Grange

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.

4.95 out of 5 average rating, 205 reviews

Red Rooster Barn

Welcome! Cozy rustic upstairs studio apartment in a renovated 100 year old barn with everything you will need. It is located within Historic Smithville on a beautiful 1/2 acre lot. The perfect place to escape and relax and enjoy time in small town Texas. While in Smithville you can shop the antique stores or dine in one of the many great restaurants. It is within 30 minutes of Circuit of The Americas, ABI Airport and shopping in Round Top. See you soon!

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Other great vacation rentals in Winchester

4.97 out of 5 average rating, 68 reviews

Guesthouse in La Grange

The Barndominium at Cedar Creek Ranch

Elizabeth And MattRating, 5 stars3 weeks ago

Frank’s place is a gem! We enjoyed the peaceful and beautiful surroundings! Thanks for the goodies and the bottle of wine, it was a plus! Elizabeth &Matt

4.97 out of 5 average rating, 29 reviews

Home in Bastrop

Cozy Retreat

AlexisRating, 5 stars2 months ago

it was a nice spot very quiet and cute! everything was a good 30-40min away !

5 out of 5 average rating, 12 reviews

The Blue Nest

SusieRating, 5 stars1 month ago

Very clean, cute, and cozy boutique airbnb in the heart of Smithville. Stylishly decorated and quiet. It is a small space, ideal for a solo traveler.

4.98 out of 5 average rating, 42 reviews

Cabin in La Grange

William’s Cabin at Rabb’s Creek Ranch

PatrickRating, 5 stars1 month ago

Mike and Diana's place was one of the best (albeit short) stays we have ever had on Airbnb. so friendly and they didn't force us to clean at the end because we had a busy day ahead. so accommodating and friendly. thank you so much!

5 out of 5 average rating, 34 reviews

Cabin in Smithville

Stargazing, hiking, woodland paradise-the Barn B&B

MankinRating, 5 stars3 weeks ago

Amazing!! That sums it up. Sandi and Stephen are wonderful people and Amazing hosts. The accommodations were exactly as described and Sandi and Stephen responded quickly with every question we had. We have been recommending thier place to our friends and are already planning our next stay.

5 out of 5 average rating, 40 reviews

Home in Smithville

Steps to Downtown, Parks, and it's Dog-friendly!

DaniseRating, 5 stars6 days ago

This was the second time to stay there. We enjoy the house it is clean and decorated so cute. Rebecca is a great hostess and is very attentive and will respond to your messages quickly. We will continue to stay there in the future.

4.89 out of 5 average rating, 37 reviews

Barn in Bastrop

Modern Barn Stay on 2.5 acres

CassandraRating, 5 stars6 days ago

The Airbnb was beautiful and the location was so relaxing. It’s close to downtown Bastrop which has cute cafes and boutiques.