Vacation rentals in Winona

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Top-rated vacation rentals in Winona

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A single-story brick house is situated on a quiet street, framed by lush greenery. The driveway leads to a double garage, while a mailbox stands at the edge of the property. A flag gently flutters from the front porch, enhancing the home’s welcoming appearance.
Home in Lindale
5 out of 5 average rating, 182 reviews

The Rita House

Centrally located in Lindale, yet back off a quiet street with a peaceful, fenced backyard with driveway parking. Up to 2 well-behaved pets are welcome! (Prior approval needed for more). It’s a quick walk to "The Cannery" which hosts Miranda Lambert's Pink Pistol and Red 55 Winery as well as Texas Music City Grill. Beautiful Darden Park and nearby dog park are also walking distance. It's also just a short drive to the quaint town of Mineola, the Texas Rose Horse Park and Canton First Mondays.

Top guest favorite
A charming black house is nestled among towering trees in a wooded setting, featuring a spacious deck that wraps around two sides. Natural light filters through the foliage, creating a serene atmosphere that invites relaxation and connection with nature.
Cabin in Tyler
4.95 out of 5 average rating, 320 reviews

The Hygge House - Respite in the forest

Escape into nature and experience the warm embrace of hygge (HYOO-gah) - a Danish word that describes a deep feeling of well-being. Nestled in a tranquil natural setting, our home is a sanctuary for slow living, rest, and fostering connection. The soft furnishings and natural light make this the perfect place to savor some of the simple pleasures of life - fresh baked cookies, a nap in our oversized deck hammock and meaningful conversation. Our hope is that you leave renewed. 12mi to Downtown

Guest favorite
A cozy outdoor space features a fire pit with a roaring flame, a picnic table, and a lantern on a gravel surface. The rustic cabin, framed by towering pine trees, is illuminated softly by an exterior light, enhancing the serene atmosphere.
Cabin in Winona
4.92 out of 5 average rating, 198 reviews

Tranquil Cabins Studio-East Texas Pines-near Tyler

Tranquil Cabins Studios are in the piney woods in Winona, TX, near Tyler, just 2 hours from DFW. Handcrafted tiny cabins inspired by nature: -Huge picture windows that immerse you in nature. -Cozy Qbed w/ cotton linens -Kitchenette w/ induction stove, mini-fridge/freezer, & utensils. -Private bath w/ hot shower, toilet & towels. Private outdoor space, w/ fire pit, chairs, & picnic table. Perfect for a romantic escape, solo retreat, or working in nature. *Wi-Fi is not for streaming

Guest favorite
A spacious seating area features a black leather sofa with contrasting orange cushions, alongside a light-colored armchair. A low wooden coffee table is placed on a textured rug. Large windows allow natural light to fill the space, complemented by indoor plants and exposed concrete walls.
Loft in Tyler
4.96 out of 5 average rating, 558 reviews

Downtown Rose Capital Studio w/ Private Sauna

The Rose Capital Studio is a unique and inspiring space. Rose Capital Studio features a 9ft wide ceiling-mounted 'backdrop' and movie projector which is perfect for entertainment. The space includes beautiful large windows, exposed concrete beams, and a private sauna for relaxation. As impressive as the space is, the best feature is likely our location. The studio is located right in the middle of Downtown - in walking distance from so many of Tyler’s best coffee-shops, restaurants, & bars.

Guest favorite
An A-Frame cabin with a distinctive wooden façade is showcased. The structure features large windows that allow natural light to fill the interior. A small patio area with two black chairs and a table is positioned at the entrance, surrounded by natural landscaping.
Cabin in Lindale
4.94 out of 5 average rating, 161 reviews

Coyote Creek A-Frame Cabin

Take it easy at this unique and tranquil A-Frame cabin in the woods, with great outdoor space and over half mile walking trail with scavenger hunt. Perfect for couples, families, solo adventurers, and business travelers. Some Items available: WiFi, Outdoor fire pit, corn hole, horseshoes, ring toss, and gathering area; Alarm Clock / Radio, Games, TV, DVDs, books, charcoal grill, full kitchen with toaster, microwave, kpod coffee maker, electric fireplace, and full size refrigerator.

Top guest favorite
An inviting deck showcases a combination of conversation lounge furniture and a bar dining set. The A-frame cabin's wooden exterior is complemented by large glass doors and windows, allowing natural light to fill the space. Surrounding trees add a serene backdrop.
Place to stay in Tyler
4.99 out of 5 average rating, 137 reviews

Piney Point A-Frame Retreat Tyler

Created to share the uniqueness of East Texas with others, Piney Point is a perfect couple or friend's retreat. Tucked in the corner of a six-acre homestead, this restored A-frame offers a modern cozy stay with an expansive deck that overlooks the spring-fed pond. Nearby are some of the best adventures East Texas has to offer, from hiking trails and fishing at Tyler State park, live music, downtown breweries, to market shopping and great food. Escape to the quiet to rest and recharge.

Guest favorite
A modern tiny home is shown, featuring a charming white exterior with black trim and a dark roof. The front porch area includes a small bench, surrounded by green grass and blooming flowers. Large windows allow natural light to fill the space.
Farm stay in Winona
4.95 out of 5 average rating, 160 reviews

Lily's Pad Peaceful stay and events welcome!

Kick back and relax in this calm, stylish space. This tiny home was built in 2022. Sitting on almost 5 acres with a pond, this place is the meaning of relaxing! Enjoy your time with a beautiful view, and unwinding from the business of the outside world. There are many choices for dining, entertainment and shopping within a few minutes drive! If you are looking to book an event, please go into the house rules and under additional rules are the terms and agreement for booking events.

Top guest favorite
The treehouse is illuminated softly against a darkening sky, perched among the trees. Its wooden structure features a spacious balcony, supported by sturdy tree trunks. The surrounding area is lined with foliage, contributing to a secluded, peaceful ambiance.
Treehouse in Lindale
4.94 out of 5 average rating, 285 reviews

Moon Honey Treehouse - Romantic Getaway - No Kids

Gorgeous treehouse escape nestled in the tree tops of Garden Valley, Tx. The perfect place for a honeymoon, anniversary or surprise romantic getaway! All the joy and imagination of a treehouse combined with elegance, modernized to help adults relax and reconnect. Enjoy coffee in the trees on the balcony, wine and cheese with a sunset view, indoor/outdoor shower. Fully stocked kitchen and outdoor hibachi grill for those who love to cook, great local restaurants for those who don’t.

Guest favorite
A private hot tub sits on the spacious deck of the cottage, surrounded by trees. The exterior includes a welcoming red door and a comfortable seating area with chairs. Natural light filters in through the windows, enhancing the outdoor living space.
Cottage in Lindale
4.92 out of 5 average rating, 404 reviews

The Cottage at Hidden Creek w/ Hot Tub and Firepit

Quaint cottage nestled among three acres of towering trees. Featuring a large, newly updated kitchen, spacious bedroom, and lots of outdoor living space including a hot tub and fire pit. This cabin in the woods offers the seclusion and East Texas beauty you seek, yet is just minutes away from numerous restaurants and attractions with easy access to Interstate 20 and Toll 49. Retreat to the large deck and gaze at the stars, or grab a blanket and enjoy s’mores by the fire.

Top guest favorite
A front porch is depicted, featuring two red chairs and a small round table. The entrance is framed by white columns and includes a welcoming white door. A decorative sign reading 'HOME' adds a personal touch, while light filters in through the windows.
Cottage in Mineola
4.97 out of 5 average rating, 142 reviews

Grannie's Guest House

My place is 6 miles east of Mineola, TX. Close to antique shopping, Mineola nature preserve, public lakes, 30 minutes to Canton First Monday trades days, and many other spotlights in East Texas. You’ll love my place because of the cozy, farmhouse atmosphere and country living. My place is good for couples, solo adventurers, and business travelers. Not suitable for kids or children, and I do not allow pets or animals of any kind on the property.

Top guest favorite
A spacious living room is highlighted by a large dark leather couch adorned with white and blue pillows. A small dog sits comfortably on the couch, surrounded by two warm lamps on side tables. Decorative plants and artwork are visible in the background, creating an inviting space.
Home in Tyler
4.94 out of 5 average rating, 269 reviews

Beautiful new home near the Tyler Airport

Bring the whole family, including the family pet (no pet fees), to this beautiful new home with lots of room to relax. This home includes a large TV in the living room for movies, games, internet and a gourmet kitchen to make meals together. Create new memories or just enjoy time together. Detailed instructions, including your Lock Code, will be shared with you after booking.

Top guest favorite
A large, sturdy tree with an expansive trunk is situated near a quaint gray cabin. A circular flower bed with blooming orange flowers surrounds the tree's base, offering a natural accent to the grassy landscape. The area is fenced, providing a pastoral setting.
Home in Gilmer
4.99 out of 5 average rating, 118 reviews

Sheep Sanctuary

Relax and enjoy being out in the country! Observe and feed sheep by ringing the bell for "mealtime"! This 448 sq. feet suite has sheep decor, including " The Lord is our Shepherd!" Bible scriptures available for reflection/ ministry! Take care of this "sanctuary!" We are grateful for you coming! Sign the guest book and our farm dog will greet you!

Popular amenities for Winona vacation rentals

  1. Airbnb
  2. United States
  3. Texas
  4. Smith County
  5. Winona