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Top Holiday Rentals in Winona

Relaxing Country Stay!

9.8 out of 10, Exceptional, (19)
"Great place to relax enjoyed feeding the dogs and ducks Accommodations were great awesome getaway "
The price is £119
includes taxes & fees
30 Jun - 1 Jul
Relaxing Country Stay!

Cozy Home Near Gregg County Airport & Lake Cherokee

10.0 out of 10, Exceptional, (4)
"Wonderful little property. Everything you need and very clean and comfortable. Host was easy to work with. I would definately stay here again."
The price is £115
includes taxes & fees
28 Jul - 29 Jul
Cozy Home Near Gregg County Airport & Lake Cherokee

Treehouse at Berry-patch

9.6 out of 10, Exceptional, (5)
"Bed was super comfy, shower was amazing, and the only thing that was missing was nice weather so we could sit on the porch in the morning. Very clean, really nicely decorated, felt like home. "
The price is £161
includes taxes & fees
28 Jul - 29 Jul
Treehouse at Berry-patch

4 bedroom 2 bath Sleeps 8

9.6 out of 10, Exceptional, (35)
"House was perfect for us to visit family that lives locally. "
The price is £352
includes taxes & fees
8 Jul - 9 Jul
4 bedroom 2 bath Sleeps 8

Charming Home in the Piney Woods of East Texas

9.6 out of 10, Exceptional, (15)
"It was perfect size for my family for the weekend. The beds were very comfortable, quiet neighborhood, and great location!"
The price is £198
includes taxes & fees
24 Jul - 25 Jul
Charming Home in the Piney Woods of East Texas

Cozy vineyard studio with peaceful pond views.

The price is £146
includes taxes & fees
14 Jul - 15 Jul
Cozy vineyard studio with peaceful pond views.

The Carriage House, The Carriage House at Jeter Farmhouse

9.0 out of 10, Wonderful, (2)
"Cousin Becky and i had a great time exploring a small country town known for their antiques. Location of guest house is spot on.Quite with all the amenities. Thanks Brad and Kristi"
The price is £102
includes taxes & fees
30 Jun - 1 Jul
The Carriage House, The Carriage House at Jeter Farmhouse

Antique Sleep or Swim in Gladewater

5.0 out of 10, (2)
"We played in a baseball tournament this weekend and decided to stay since we live in Louisiana. The place was very clean. Very new! Absolutely beautiful! The only complaint we had is that there was not very much hot water. I’m not sure if the hot water heater was broken or what…. I hope the owners or management gets it fixed."
The price is £257
includes taxes & fees
30 Jun - 1 Jul
Antique Sleep or Swim in Gladewater

Lakeside Retreat on Lake Gladewater

9.0 out of 10, Wonderful, (7)
"Great place for weekend getaway"
The price is £463
includes taxes & fees
30 Jun - 1 Jul
Lakeside Retreat on Lake Gladewater

Casa del Lago at Sandy Point ~ Charming 3 bedroom house with amazing lake views

The price is £217
includes taxes & fees
1 Jul - 2 Jul
Casa del Lago at Sandy Point ~ Charming 3 bedroom house with amazing lake views

Fabulous 3-bedroom house with AC in charming Tyler

2.0 star property
The price is £256
includes taxes & fees
30 Jun - 1 Jul
Fabulous 3-bedroom house with AC in charming Tyler

Cozy 2 bedroom 2 bath duplex near UT Tyler!

9.8 out of 10, Exceptional, (30)
"Host was wonderful. Clean play and a perfect place to stay for our trip."
The price is £150
includes taxes & fees
5 Jul - 6 Jul
Cozy 2 bedroom 2 bath duplex near UT Tyler!

Stay Tyler @ Parade of Homes

10.0 out of 10, Exceptional, (23)
"We stayed here for a couple of nights to celebrate my daughter’s birthday. We loved it! Lots of space, very clean, and comfortable! Will definitely stay here again if back in Tyler!"
The price is £274
includes taxes & fees
30 Jun - 1 Jul
Stay Tyler @ Parade of Homes

Stay Tyler @Royal Hills

10.0 out of 10, Exceptional, (6)
"This was a great place to stay for the birthday weekend. Clean and has all needed amenities. I would definitely stay here again."
The price is £246
includes taxes & fees
6 Jul - 7 Jul
Stay Tyler @Royal Hills

Rest A While Townhome

8.0 out of 10, Very good, (4)
"Served our needs for my hospital stay."
The price is £253
includes taxes & fees
30 Jun - 1 Jul
Rest A While Townhome

A Gem on 5th St

2.0 star property
9.0 out of 10, Wonderful, (2)
"All was to standard: cozy, efficient, amenities of home like the washer and dryer. As a family, we would stay here again. Only thing to note that I would have loved to be aware is the bathroom amenity of soap and shampoo. The listing says it is provided and was not near enough for my family and a two night stay. No stress, just would have liked to be prepared ahead of time.Also a note of hospitality- there are no extra blankets aside from the beds provided. So when sitting on the couch, you...
The price is £245
includes taxes & fees
7 Jul - 8 Jul
A Gem on 5th St

3br duplex centrally located!

6.0 out of 10, (2)
"WORST stay we have had in a Vrbo. The duplex reeked of pot/weed everyday, even the night we got there at 10pm. Contacted the lady who owns it and never received a call back or an email after she said she’d go take a look. I asked for a call back there was no further communication between her and I. There were multiple items broken or damaged in the duplex. The shower had mold in it, the master bathroom was not cleaned before we got there. There was also mouse poop all over in the hot water...
The price is £316
includes taxes & fees
6 Jul - 7 Jul
3br duplex centrally located!

Green Acres District, Sleeps 8, King/Queen

10.0 out of 10, Exceptional, (19)
"Great place!"
The price is £241
includes taxes & fees
30 Jun - 1 Jul
Green Acres District, Sleeps 8, King/Queen

Welcome Home!

8.8 out of 10, Excellent, (19)
"Overall a nice house to stay in, just a couple of things I would have liked to see cleaner. I also had to be the one to reach out to get check in instructions."
The price is £313
includes taxes & fees
30 Jun - 1 Jul
Welcome Home!

Piece of Paradise: Pool, Pickleball, Pond, Privacy

9.6 out of 10, Exceptional, (17)
"We had a great time staying here while in town for our son’s college graduation. Great place for grandparents and families to converge and hang out."
The price is £454
includes taxes & fees
2 Jul - 3 Jul
Piece of Paradise: Pool, Pickleball, Pond, Privacy
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals in Winona close to Mrs. Lee's Daffodil Garden, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winona has to offer?

Relaxing Lake View Retreat in Mineola , TX: This holiday home rental outside of Winona is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Winona?

Explore the area and family-friendly sights such as Caldwell Zoo, or get out into nature at a spot like Mrs. Lee's Daffodil Garden. Tyler State Park and Brumley Lake are a couple of places you'll find in the wider area.

What’s a holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips.