Best Vacation Homes in Winona
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
US $140/Night
For 7 Nights US $977
1280.91 ft²
4 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $282/Night
For 7 Nights US $1,976
1100 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $153/Night
For 7 Nights US $1,074
1500 ft²
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $240/Night
For 7 Nights US $1,681
2400.35 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $141/Night
For 7 Nights US $989
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $225/Night
For 7 Nights US $1,573
720 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $267/Night
For 7 Nights US $1,866
1300 ft²
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $292/Night
For 7 Nights US $2,041
Winona Luxury Rentals
5328 ft²
12 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $673/Night
For 7 Nights US $4,712
16 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $660/Night
For 7 Nights US $4,620
16 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $624/Night
For 7 Nights US $4,368
3600 ft²
13 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $561/Night
For 7 Nights US $3,929
53819.55 ft²
14 Guests
6 Bedrooms
3 Bathrooms
House
- Parking
- Internet
- Child Friendly
US $500/Night
For 7 Nights US $3,500
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $376/Night
For 7 Nights US $2,632
2500 ft²
16 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $365/Night
For 7 Nights US $2,552
1905.21 ft²
8 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Parking
- Internet
US $338/Night
For 7 Nights US $2,364
Winona Pet Friendly Vacation Rentals
1276 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $211/Night
For 7 Nights US $1,479
139.93 ft²
2 Guests
1 Bedroom
1 Bathroom
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $95/Night
For 7 Nights US $665
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $197/Night
For 7 Nights US $1,379
720 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $263/Night
For 7 Nights US $1,838
602.78 ft²
5 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $175/Night
For 7 Nights US $1,227
1323 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $218/Night
For 7 Nights US $1,527
1288 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $227/Night
For 7 Nights US $1,588
1000 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $152/Night
For 7 Nights US $1,066
Winona Large Vacation Homes
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Child Friendly
US $160/Night
For 7 Nights US $1,120
3196.88 ft²
9 Guests
5 Bedrooms
2 Bathrooms
House
- Parking
- Child Friendly
US $270/Night
For 7 Nights US $1,890
361.67 ft²
61 Guests
73 Bedrooms
11 Bathrooms
Other
- Pool
- Air Conditioner
- Internet
US $282/Night
For 7 Nights US $1,976
Why Choose Rent By Owner for your Winona Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Winona
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can significantly enhance your experience, as the climate and local events in this region vary throughout the year, making it ideal for planning your stays in vacation rentals that suit your preferred season.
Peak Season Highlights
Spring (March to May)
During the spring months, you can enjoy pleasant weather and vibrant natural scenery, making it an ideal time for outdoor activities in this destination.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Fall (September to November)
The fall season offers cooler temperatures and colorful foliage, perfect for exploring the region's scenic outdoors and enjoying a serene getaway.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Summer (June to August)
While summer can bring higher temperatures, it remains a lively time to visit with longer days and opportunities for outdoor relaxation in this area.
Average Temperature Daytime: 85°F to 95°F - Nighttime: 65°F to 75°F
Winter (December to February)
Winters tend to be milder here compared to other regions, but this is typically the quietest period for visits, offering a peaceful retreat away from peak crowds.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Winona
How to Book Your Winona Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winona
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a spacious patio or deck for relaxing and entertaining.
- Take advantage of well-maintained BBQ grills for outdoor cooking in the region's pleasant climate.
- Relax by a sparkling swimming pool, perfect for cooling off during warmer months here.
- Benefit from access to lush gardens or landscaped yards that enhance your outdoor experience.
- Make the most of outdoor dining areas, ideal for enjoying meals surrounded by the area's natural beauty.
- Utilize designated fire pits or outdoor fireplaces for cozy gatherings in this destination.
- Explore nearby trails or open spaces through convenient outdoor amenities provided on-site.
Top Attractions Around Winona
What attractions are nearby?
While staying here, you'll have the opportunity to explore nearby outdoor activities, local parks, and scenic spots that showcase the natural beauty of the region, ensuring an enjoyable and relaxing visit.
Family Activities
- Winona Lake Park: You can enjoy a relaxing day outdoors by exploring walking trails, picnic areas, and playgrounds in this scenic local park.
- Jewett Community Center: Engage in family-friendly activities and recreational programs offered at the community center to make your stay more enjoyable.
- Museum of East Texas Culture: Discover the region's history through engaging exhibits and interactive displays perfect for family outings.
- Local Wildlife Viewing Areas: Experience nature and observe native animals in their habitat at nearby wildlife viewing spots suited for all ages.
Adult Activities
- Winona Lake Park: Enjoy a leisurely day exploring scenic walking trails, fishing spots, and picnic areas in this peaceful lakeside setting within the region.
- Winona Historic District: Discover charming architecture and local history as you stroll through this well-preserved neighborhood that highlights the area's cultural heritage.
- Winona Nature Preserve: Experience the tranquility of nature with birdwatching and hiking opportunities nestled within the natural beauty surrounding here.
- Local Art Galleries: Immerse yourself in the region's vibrant arts scene by visiting galleries showcasing works from talented regional artists.
Other Places to Stay in Winona, TX
Starrville
Winona Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the area’s natural beauty by engaging in nearby outdoor pursuits such as hiking or fishing to fully enjoy your stay in this scenic destination.
- Plan ahead for amenities: Check the available amenities at your vacation rental in the region to ensure a comfortable and convenient experience during your visit here.
- Discover nearby dining options: Savor authentic regional cuisine by exploring popular dining spots close to your accommodation, enhancing your overall trip experience.
- Engage with local events and culture: Participate in community events or cultural activities to gain a deeper appreciation of this destination’s unique heritage while visiting here.
Transportation Options
- Personal Vehicles: Renting or driving your own car provides the most flexibility to explore this destination and its surrounding areas at your own pace.
- Local Taxi Services: Taxis are readily available for convenient transportation within the region, offering a reliable way to reach local attractions and amenities.
- Rideshare Options: Rideshare services like Uber and Lyft operate here, giving you an easy and affordable way to navigate the area without the need for a personal vehicle.
- Public Transit: Buses serve the region, providing an economical and accessible option for getting around during your stay.
Local Customs Options
- Southern Hospitality: The area prides itself on welcoming visitors with genuine warmth and friendliness, making your stay here feel like a homecoming.
- Community Festivals: Local celebrations often highlight traditional music, food, and crafts that reflect the region's rich cultural heritage.
- Respect for Nature: Here, you’ll notice a deep appreciation for the natural landscape, with customs emphasizing conservation and outdoor enjoyment.
- Historical Preservation: Maintaining historic sites and practices is a common way residents honor the area's past and pass down traditions.
Winona Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Winona?
There are a lot of options in Winona. If you plan on staying in the Winona area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winona:
- Willow's Cabin - Cozy Cabin Nestled In The Woods
- 6 BR Log Home in Piney Woods of East TX with hot tub and POND
- Cora's Main Log Cabin
- Relaxing Country Stay with Events Welcome!
- Lake Gladewater lake house - come relax ,watch the sunset or jump off the dock.
- Cozy Cabin in Big Sandy
- Casa del Lago at Sandy Point ~nCharming 3 bedroom house with amazing lake views
- Jellystone Park Tyler
- Fire Pit & Grill: Tyler Home on 5 Acres!
- The Texas Roost - 1-bedroom country guest house 7.4 miles to Kilgore College.
2. Which vacation homes in Winona are best for families?
If you are looking for a family-friendly vacation home in Winona, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winona:
3. How many Rentbyowner vacation rentals are available in Winona?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 117 in the Winona area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winona.
4. What is the cancellation policy for vacation rentals in Winona, Texas?
Each property listing has its own cancellation terms. You should review the specific cancellation policy before confirming your booking to understand any potential fees or restrictions.
5. How do I communicate with the property owner in Winona, Texas, prior to booking?
You can contact the property owner directly through the messaging system provided on the booking platform to ask questions or clarify details about the vacation rental in this area.
6. Are there any house rules I should be aware of when staying in a vacation rental in Winona, Texas?
Yes, each vacation rental typically includes house rules that you must follow during your stay. These are usually detailed in the listing and are provided upon booking confirmation.
7. Is Wi-Fi included in vacation rentals in Winona, Texas?
Many properties in this region offer Wi-Fi, but it’s best to check the amenities listed on the property page to confirm availability for your chosen rental.
8. What is the process for checking in and out of vacation rentals in Winona, Texas?
Check-in and check-out procedures vary by property. Details are provided in the listing, or you can inquire directly with the property owner for specific instructions.
Winona Top Rated Vacation Rentals
226.04 ft²
2 Guests
1 Bedroom
1 Bathroom
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $161/Night
For 7 Nights US $1,125
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $189/Night
For 7 Nights US $1,323
2160 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $492/Night
For 7 Nights US $3,442
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $758/Night
For 7 Nights US $5,305
900 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $89/Night
For 7 Nights US $623
