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 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, 329 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, 206 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 warm and inviting kitchen area is highlighted by wooden beams and log walls. A stone stove serves as a focal point next to large windows, allowing natural light to fill the space. A simple dining table and chairs create a cozy dining setting.
Cabin in Mineola
5 out of 5 average rating, 31 reviews

The Cabin at The Pine Retreat

Welcome to a little slice of heaven at The Pine Retreat. The Cabin was inspired by the idea of feeling secluded, surrounded by nature, but in style. Framed by gorgeous pine logs accented with mid-century modern flare, this is the perfect romantic getaway, family retreat, or just a place to take a break from the city. Soak in the cedar hot tub and gaze up at the stars with a gorgeous pond as the ultimate backdrop. 5 mins from downtown Mineola, 9 mins from Mineola Country Club & Lake Holbrook.

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, 568 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.

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, 142 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.

Top guest favorite
Home in Tyler
5 out of 5 average rating, 13 reviews

Modern Farmhouse Retreat W/Pool Table & Fire Pit

Secluded Modern Farmhouse Retreat |Pond, Paddle Boats, Fire Pit, Pool Table, Fresh Eggs | 4 Beds, 2 Bathrooms, Sleeps 8| Designer Soaking Tub, 2 Luxury Showers, Modern Fully Functional Kitchen| Perfect for Families, Group Vacation Stay, Bachelor/Bachelorette Party House, Couples Weekend Retreat PRIVATE OUTDOOR RETREAT + UNIQUE EXPERIENCES ✔️ Pool Table & Game room ✔️ Private pond ✔️Paddle Boats ✔️Outdoor fire pit ✔️Front & back porch ✔️Chickens on-site for collecting fresh eggs

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
4.94 out of 5 average rating, 163 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.

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, 418 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
The exterior of the main house is shown, featuring a white facade with a sloped roof and large glass doors. Surrounded by lush greenery, the spacious lawn provides ample outdoor space for relaxation. A patio area with seating enhances the tranquil setting.
Farm stay in Winona
4.95 out of 5 average rating, 21 reviews

Pine Hill Farm, House and Guest House

Enjoy the sounds of nature while staying at this peaceful farm near Tyler on 35 acres with a private lake, main house, guest house, boat dock and multiple outdoor entertaining areas. A total of 4 bedrooms and 3 full baths, 2 kitchens, multiple living and dining areas. This gated , private compound is a perfect place for large family gatherings. Explore nature, fish from the dock, sit by the fire pit, play games, read and relax! Close to Tyler and Lindale.

Top guest favorite
A wooden table with a patterned tabletop is accompanied by a matching stool, situated on a grassy area. String lights overhead provide soft illumination, creating an inviting atmosphere near a fire pit surrounded by Adirondack chairs and stacked firewood.
Cabin in Lindale
4.97 out of 5 average rating, 30 reviews

The Casita @ Tall Pine Cabins

Escape and immerse yourself in the tranquility of nature at Tall Pine Cabins.  A unique experience under the stars and within a few minutes of all that the East Texas Piney Woods has to offer. The Casita is a cozy tiny home with modern amenities, outdoor fire pit and activities, with a backdrop of tall pine trees in the East Texas Piney woods. Enjoy the outdoors with a great patio and deck with outdoor dining. Just minutes from Tyler State Park and more.

Top guest favorite
A firepit area is surrounded by four adirondack chairs, two in black and two in blue, positioned on sandy ground. The tranquil waters of Lake Hawkins reflect the soft pastel hues of the sunset, with a boat dock and gazebo visible in the background.
Cottage in Hawkins
4.89 out of 5 average rating, 111 reviews

Lakehouse - Sleeps 6, Dock, Fire Pit, Kayaks

Welcome to GRIF's GETAWAY. A cozy vintage cottage on Lake Hawkins. Enjoy 2 bedrooms with antique queen beds, a 4-pc bath, and a queen sleeper sofa in the living room. Relax with vintage linens, closet space, and modern comforts. Outside, take advantage of the private dock, firepit, and 2 kayaks. Nestled among trees with tranquil lake views-perfect for a weekend escape or longer retreat!

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
4.95 out of 5 average rating, 280 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.

Popular amenities for Winona vacation rentals

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