Holiday Homes in Winona

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Winona and around

Relaxing Country Stay with Events Welcome!
Fridge, microwave, oven, stovetop

Relaxing Country Stay with Events Welcome!

9.8 out of 10, Exceptional, (19)
"It was very cozy and clean, me and my partner had a very comfortable stay"
Relaxing Country Stay with Events Welcome!
Historic House, modern amenities and large front porch, short walk downtown
Exterior

Historic House, modern amenities and large front porch, short walk downtown

2.0 star property
8.6 out of 10, Excellent, (4)
"The house was lovely and offered historic charm as well as modern comforts. It is walking distance to shops and restaurants. The hosts were attentive and gave clear and easy instructions. Note that the house is close to the railroad tracks and the occasional train can be heard, including in the middle of the night. "
The price is €140
includes taxes & fees
3 Sept - 4 Sept
Historic House, modern amenities and large front porch, short walk downtown
Cozy Home Near Gregg County Airport & Lake Cherokee
Smart TV

Cozy Home Near Gregg County Airport & Lake Cherokee

9.6 out of 10, Exceptional, (5)
"Wonderful little property. Everything you need and very clean and comfortable. Host was easy to work with. I would definately stay here again."
Cozy Home Near Gregg County Airport & Lake Cherokee
Spacious 1-Bedroom Guesthouse in the Woods
Fridge, microwave, oven, stovetop

Spacious 1-Bedroom Guesthouse in the Woods

10.0 out of 10, Exceptional, (42)
"Really roomy and great price"
The price is €112
includes taxes & fees
22 Sept - 23 Sept
Spacious 1-Bedroom Guesthouse in the Woods
Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!
Fridge, microwave, stovetop, coffee/tea maker

Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!

9.2 out of 10, Wonderful, (28)
"Great place to stay!"
Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!
Cozy vineyard studio with peaceful pond views.
Exterior

Cozy vineyard studio with peaceful pond views.

10.0 out of 10, Exceptional, (1)
"I can’t say enough good things about the host and our stay! Everything was super clean, comfortable, and peaceful. I loved the layout, and every detail—from the bed to the blanket on the couch—was incredibly cozy. I highly recommend staying here, and we’re already planning to come back."
Cozy vineyard studio with peaceful pond views.
Casa del Lago at Sandy Point ~ Charming 3 bedroom house with amazing lake views
Property grounds

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

10.0 out of 10, Exceptional, (1)
"The home is beautiful and in an amazing location it was very clean and Julie is an amazing host and she responded so quickly to any questions "
The price is €280
includes taxes & fees
24 Aug - 25 Aug
Casa del Lago at Sandy Point ~ Charming 3 bedroom house with amazing lake views
The Carriage House, The Carriage House at Jeter Farmhouse
Exterior

The Carriage House, The Carriage House at Jeter Farmhouse

9.6 out of 10, Exceptional, (4)
"Very nice rental "
The price is €121
includes taxes & fees
22 Sept - 23 Sept
The Carriage House, The Carriage House at Jeter Farmhouse
Treehouse at Berry-patch
Exterior

Treehouse at Berry-patch

8.4 out of 10, Very good, (6)
"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 €185
includes taxes & fees
24 Aug - 25 Aug
Treehouse at Berry-patch
Cozy Lakefront 2-bedroom cabin in tranquil Big Sandy, TX.
Microwave, oven, stovetop, paper towels

Cozy Lakefront 2-bedroom cabin in tranquil Big Sandy, TX.

Cozy Lakefront 2-bedroom cabin in tranquil Big Sandy, TX.
Cozy 2 bedroom 2 bath duplex near UT Tyler!
Smart TV, fireplace

Cozy 2 bedroom 2 bath duplex near UT Tyler!

9.8 out of 10, Exceptional, (33)
"Host was wonderful. Clean play and a perfect place to stay for our trip."
The price is €169
includes taxes & fees
26 Aug - 27 Aug
Cozy 2 bedroom 2 bath duplex near UT Tyler!
Charming 3-bedroom house on quiet street in delightful Kilgore
Microwave, oven, stovetop, dishwasher

Charming 3-bedroom house on quiet street in delightful Kilgore

The price is €197
includes taxes & fees
23 Sept - 24 Sept
Charming 3-bedroom house on quiet street in delightful Kilgore
Charming townhome w/King Bed- Close to Everything in Tyler!
Terrace/patio

Charming townhome w/King Bed- Close to Everything in Tyler!

Charming townhome w/King Bed- Close to Everything in Tyler!
Quiet house in the country - 20 minutes from Canton and Lake Fork!
Fridge, microwave, oven, stovetop

Quiet house in the country - 20 minutes from Canton and Lake Fork!

10.0 out of 10, Exceptional, (29)
"The house was great cute, clean and cozy. Would stay again!"
Quiet house in the country - 20 minutes from Canton and Lake Fork!
Fabulous 3-bedroom house with AC in charming Tyler
Fridge, microwave, oven, stovetop

Fabulous 3-bedroom house with AC in charming Tyler

2.0 star property
Fabulous 3-bedroom house with AC in charming Tyler
Lakeside Retreat on Lake Gladewater
Pool

Lakeside Retreat on Lake Gladewater

9.0 out of 10, Wonderful, (10)
"Great place to relax and chill with friends."
The price is €670
includes taxes & fees
24 Aug - 25 Aug
Lakeside Retreat on Lake Gladewater
Kirk’s Kilgore Kottage - 3 bedrooms, 2 bath House
Fridge, microwave, oven, stovetop

Kirk’s Kilgore Kottage - 3 bedrooms, 2 bath House

Kirk’s Kilgore Kottage - 3 bedrooms, 2 bath House
Charming Home in the Piney Woods of East Texas
Dining

Charming Home in the Piney Woods of East Texas

9.4 out of 10, Exceptional, (17)
"It was perfect size for my family for the weekend. The beds were very comfortable, quiet neighborhood, and great location!"
Charming Home in the Piney Woods of East Texas
THE ALAMO HOUSE King size bed Fast internet!
Fridge, microwave, oven, stovetop

THE ALAMO HOUSE King size bed Fast internet!

10.0 out of 10, Exceptional, (41)
"Great house & location!Clean and great host!Highly recommend!"
THE ALAMO HOUSE King size bed Fast internet!
Welcome to Jackson Hole A Charming 1-bedroom house in Historic Mineola.
Fridge, microwave, oven, stovetop

Welcome to Jackson Hole A Charming 1-bedroom house in Historic Mineola.

10.0 out of 10, Exceptional, (2)
"What a great little place to stay! Had everything we needed and felt right at home :))"
Welcome to Jackson Hole A Charming 1-bedroom house in Historic Mineola.
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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Top Winona Hotel Reviews

12 Oaks Hotel

12 Oaks Hotel

10/10 Excellent
"If I came back a second time it was great. My grandkids enjoyed it. I'm not sure if you have a lifeguard at the swimming pool because my daughter was there. If there is another time that my grandkids stay there if a lifeguard is not present they will not stay there but I will. I say that because my youngest grandchild love the water so I don't want him to go swimming without her consent and no one is present to save him. "
Leon 1-night trip
Posted 1 day ago
12 Oaks Hotel