Holiday houses in Winona

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Top-rated holiday rentals in Winona

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Guest favourite

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

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

4.92 out of 5 average rating, 209 reviews

Top Guest favourite

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

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.

4.99 out of 5 average rating, 146 reviews

Top Guest favourite

Home in Tyler

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

5.0 out of 5 average rating, 30 reviews

Guest favourite

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

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.

4.94 out of 5 average rating, 165 reviews

Top Guest favourite

A charming two-story house is surrounded by vibrant flower beds and well-maintained landscaping. A spacious patio greets guests, featuring a bar area and decorative lighting. The gravel pathway leads to the entrance, showcasing a welcoming atmosphere amidst lush greenery.

Home in Gladewater

Rural Paradise, Fishing, Games, Seclusion

Message us to find out about 3 day weekend discounts! 10 minutes off Interstate 20. Bring friends & family! Find a "My Space" & chill. There's lots! Cook some stuff! No close neighbors. All bedrooms have T.V.! The pergola swing is a great place to enjoy a private waterfront view! Lots of coffee & tea! Stocked pantry w free & avail/purchase snacks & drinks! FULL kitchen inside & outside too! Make a milk shake! Take a walk, cook, eat, yard games, or go fishing - GO AMERICANA!

4.98 out of 5 average rating, 181 reviews

Top Guest favourite

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

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.

4.93 out of 5 average rating, 433 reviews

Top Guest favourite

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

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.

4.95 out of 5 average rating, 21 reviews

Top Guest favourite

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

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.

4.97 out of 5 average rating, 33 reviews

Guest favourite

Apartment in Tyler

Spacious 3BR in Tyler | Perfect for Extended Stays

If you're looking for a peaceful, fully-furnished space near Tyler for an extended stay, you've found it. Our spacious 3BR/2BA apartment offers a quiet country setting just minutes from town. Perfect for families in transition, travel nurses, or professionals working nearby. With a fully fenced yard, in-unit laundry, and plenty of space to settle in, it’s designed to feel like home during your stay.

4.88 out of 5 average rating, 34 reviews

Guest favourite

Home in Lindale

Country Living

Bring the whole family to this great place with lots of room for fun.Located 6.8 miles away from Tyler State Park,11 miles from lake Hawkins.Looking for a good hangout spot to eat?This house is 6.8 miles away from circle M Crawfish or if you want to grocery shop and cook for yourself Brookshires is 6 minutes away as well as the Dollar general and Sonic. Tyler's East NE Loop 323 is 20 minutes away.

4.83 out of 5 average rating, 86 reviews

Guest favourite

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

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!

4.88 out of 5 average rating, 112 reviews

Top Guest favourite

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

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.

4.95 out of 5 average rating, 286 reviews