Winona Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Winona vacation rentals

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

Vacation Home in Winona

Relaxing Country Stay with Events Welcome!
9.8 out of 10, Exceptional, (19)
"Great place to relax enjoyed feeding the dogs and ducks Accommodations were great awesome getaway "
United States
Ray T.
$151 nightly
The price is $159
Dec 11 - Dec 12
Total with taxes and fees
Relaxing Country Stay with Events Welcome!
Exterior detail
Cana Cottage | Farm Stay

Cottage in Tyler

Cana Cottage | Farm Stay
10.0 out of 10, Exceptional, (43)
"Good design, well maintained "
United States
William
$109 nightly
The price is $114
Dec 15 - Dec 16
Total with taxes and fees
Cana Cottage | Farm Stay
1 bedroom, desk, iron/ironing board, free WiFi
The Cottage at Dogwood Ridge.

Cottage in Whitehouse

The Cottage at Dogwood Ridge.
10.0 out of 10, Exceptional, (108)
"The Cottage was very clean, area is quiet and "
United States
Patricia H.
$160 nightly
The price is $168
Dec 14 - Dec 15
Total with taxes and fees
The Cottage at Dogwood Ridge.
The Tree House Cabin | Individually decorated, individually furnished, laptop workspace
Cora's Cabins

Cabin in Tyler

Cora's Cabins
3.0 star property
9.4 out of 10, Exceptional, (155)
"Enjoyed the stay "
United States
Benito
$144 nightly
The price is $151
Dec 18 - Dec 19
Total with taxes and fees
Cora's Cabins
Property grounds
Cozy cabin in charming Hawkins with AC

Cabin in Hawkins

Cozy cabin in charming Hawkins with AC
9.0 out of 10, Wonderful, (9)
"Thelma did a great job of taking care of us. The hot tub was amazing. A good place to get away from the everything. Pet friendly. "
United States
Benny G.
$120 nightly
The price is $133
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy cabin in charming Hawkins with AC
Fridge, microwave, oven, stovetop
Guesthouse on peaceful 11+ acre homestead! Pet friendly!

Vacation Home in Tyler

Guesthouse on peaceful 11+ acre homestead! Pet friendly!
10.0 out of 10, Exceptional, (31)
"Our family had a great time staying here! The kids LOVED the loft, the sheep, & the livestock guardian dog Roxy! "
United States
Kayla B.
$109 nightly
The price is $114
Dec 15 - Dec 16
Total with taxes and fees
Guesthouse on peaceful 11+ acre homestead! Pet friendly!
Interior
The Happy Pine Cone :)

Cabin in Tyler

The Happy Pine Cone :)
9.8 out of 10, Exceptional, (37)
"Very cute little cabin"
United States
David s.
$145 nightly
The price is $151
Dec 16 - Dec 17
Total with taxes and fees
The Happy Pine Cone :)
Pool
Cozy Wood Cottage in Tyler

Cabin in Tyler

Cozy Wood Cottage in Tyler
2.0 star property
8.0 out of 10, Very Good, (1)
"The cabin was very clean & cozy, however the television did not work so that made for a little too much quiet time! "
United States
Chris J.
$110 nightly
The price is $115
Dec 12 - Dec 13
Total with taxes and fees
Cozy Wood Cottage in Tyler
1 bedroom, WiFi, bed sheets
The Tree House Cabin

Cabin in Tyler

The Tree House Cabin
9.6 out of 10, Exceptional, (25)
"Very nice and quiet place to stay. Was as described in listing. Would stay again."
United States
Jim M.
$160 nightly
The price is $167
Dec 11 - Dec 12
Total with taxes and fees
The Tree House Cabin
Microwave, oven, stovetop
Home away from Home- Near Tyler Airport

Cabin in Tyler

Home away from Home- Near Tyler Airport
10.0 out of 10, Exceptional, (3)
"Very cute place with everything we needed for a peaceful and relaxing stay. The stars and moon were beautiful that night out in the country. "
United States
Jennifer G.
$122 nightly
The price is $128
Dec 11 - Dec 12
Total with taxes and fees
Home away from Home- Near Tyler Airport
Interior
The Lazy Squirrel Cabin

Cabin in Tyler

The Lazy Squirrel Cabin
9.6 out of 10, Exceptional, (36)
"I was looking for a few days of weekday retreat and found it. There were a few other guests on the property but it still was quiet and peaceful. If you're looking for an escape from Dallas Fort Worth that's not an all day drive then this is it!"
United States
Marc A.
$155 nightly
The price is $161
Dec 11 - Dec 12
Total with taxes and fees
The Lazy Squirrel Cabin
Exterior
The Carriage House, The Carriage House at Jeter Farmhouse

Vacation Home in Gladewater

The Carriage House, The Carriage House at Jeter Farmhouse
9.6 out of 10, Exceptional, (9)
"Very nice rental "
United States
michael S.
$129 nightly
The price is $135
Dec 11 - Dec 12
Total with taxes and fees
The Carriage House, The Carriage House at Jeter Farmhouse
Exterior
Treehouse at Berry-patch

Vacation Home in Longview

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. "
United States
Leslie K.
$199 nightly
The price is $210
Dec 11 - Dec 12
Total with taxes and fees
Treehouse at Berry-patch
Pool
The Floret Cottage

Cottage in TYLER

The Floret Cottage
10.0 out of 10, Exceptional, (2)
"Great location! We enjoyed the wonderful amenities and personal care services offered! "
United States
Kimberly G.
$292 nightly
The price is $307
Dec 14 - Dec 15
Total with taxes and fees
The Floret Cottage
Smart TV
Cozy Home Near Gregg County Airport & Lake Cherokee

Vacation Home in Longview

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."
United States
Teri T.
$140 nightly
The price is $147
Jan 8 - Jan 9, 2026
Total with taxes and fees
Cozy Home Near Gregg County Airport & Lake Cherokee
Fridge, microwave, stovetop, coffee/tea maker
Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!

Vacation Home in Mineola

Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!
9.2 out of 10, Wonderful, (30)
"Beautiful location tiny home is immaculate condition. It was only an overnight trip, but it was well worth it. Will be looking forward to another stay when possible."
United States
Jeffry A.
$157 nightly
The price is $175
Dec 11 - Dec 12
Total with taxes and fees
Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!
Interior
Charming and Historic Holly Cottage Carriage House in Downtown Tyler

Cottage in Tyler

Charming and Historic Holly Cottage Carriage House in Downtown Tyler
2.0 star property
9.8 out of 10, Exceptional, (27)
"Good location. Nice neighborhood. Parking was on the street but very little to no traffic so it was ok. The host responded quickly and was very helpful. "
United States
Patricia R.
$145 nightly
The price is $152
Dec 11 - Dec 12
Total with taxes and fees
Charming and Historic Holly Cottage Carriage House in Downtown Tyler
Exterior
Historic House, modern amenities and large front porch, short walk downtown

Vacation Home in Mineola

Historic House, modern amenities and large front porch, short walk downtown
2.0 star property
8.8 out of 10, Excellent, (5)
"Its a very cute and cozy place. "
United States
Thomas S.
$150 nightly
The price is $158
Dec 11 - Dec 12
Total with taxes and fees
Historic House, modern amenities and large front porch, short walk downtown
Interior
Chic Suite in Central Longview King Bed

Apartment in Longview

Chic Suite in Central Longview King Bed
10.0 out of 10, Exceptional, (21)
"Loved the loft- clean and secure. "
United States
Jessica H.
$256 nightly
The price is $290
Jan 1 - Jan 2, 2026
Total with taxes and fees
Chic Suite in Central Longview King Bed
Microwave, oven, stovetop, dishwasher
Charming 3-bedroom house on quiet street in delightful Kilgore

Vacation Home in Kilgore

Charming 3-bedroom house on quiet street in delightful Kilgore
9.4 out of 10, Exceptional, (3)
"Clean home, excellent host"
United States
Ashley S.
$204 nightly
The price is $215
Dec 11 - Dec 12
Total with taxes and fees
Charming 3-bedroom house on quiet street in delightful Kilgore
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

Hilton Garden Inn Tyler

Hilton Garden Inn Tyler

10/10 Excellent
"Breakfast was great But Hot Tub was shut down a couple times"
Kathy 2-night trip
Posted 2 days ago
Hilton Garden Inn Tyler

Find out more about Winona

Everything you need to know about Winona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winona vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $114 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Winona?

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

What are some of the best vacation home rentals in Winona?

Relaxing Country Stay with Events Welcome!: This Winona vacation home rental offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Winona?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Winona stay.

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 Jarvis Christian College are a couple of places you'll find in the larger area.

What’s a vacation rental in Winona like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winona. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.