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Winona Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winona vacation rentals

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

1. Relaxing Country Stay with Events Welcome!

Relaxing Country Stay with Events Welcome!
Winona
10.0 out of 10, Exceptional, (28 reviews)
"Everything about this property is excellent; great hosts, beautiful property, super clean, everything you need to feel at home."
United States
Susan C.
$170 nightly
The price is $179
Oct 20 - Oct 21
Total with taxes and fees
Relaxing Country Stay with Events Welcome!
A wooden cabin with a staircase leading to a porch, surrounded by trees.

2. Cora's Cabins

Cora's Cabins
3.0 star property
Tyler
9.4 out of 10, Exceptional, (162 reviews)
"We had a lovely time at the Barn Loft. Such pretty decor, comfy bed, and shower. We were greeted by Bingo the cat and the property owner. The Flying H Ranch is an East Texas delight!"
United States
Kelly
$145 nightly
The price is $152
Oct 15 - Oct 16
Total with taxes and fees
Cora's Cabins
A covered porch with wooden flooring, a ceiling fan, and a bench with cushions.

3. The Happy Pine Cone :)

The Happy Pine Cone :)
Tyler
9.8 out of 10, Exceptional, (38 reviews)
"Very cute little cabin"
United States
David s.
$149 nightly
The price is $155
Oct 12 - Oct 13
Total with taxes and fees
The Happy Pine Cone :)
A small, green cabin with a wooden deck, a patio table, and chairs.

4. 7 Mi to Tyler State Park: 'A-Game' Cabin

7 Mi to Tyler State Park: 'A-Game' Cabin
Tyler
9.6 out of 10, Exceptional, (5 reviews)
"Clean house. Pet friendly. Great for a weekend getaway. "
United States
Justin S.
$206 nightly
The price is $217
Oct 12 - Oct 13
Total with taxes and fees
7 Mi to Tyler State Park: 'A-Game' Cabin
A spacious hallway with wooden flooring, a dining area, a kitchen, and a living space.

5. Hike & Explore: 60-Acre Outdoor Retreat in Tyler!

Hike & Explore: 60-Acre Outdoor Retreat in Tyler!
Tyler
9.8 out of 10, Exceptional, (8 reviews)
"Absolutely adorable stay and fun things for kids to do on the property."
United States
trish c.
$224 nightly
The price is $236
Oct 12 - Oct 13
Total with taxes and fees
Hike & Explore: 60-Acre Outdoor Retreat in Tyler!
A compact living space with a built-in sofa, a coffee table, a small rug, and a wooden staircase.

6. Cozy Tiny Home in Heart of Big Sandy

Cozy Tiny Home in Heart of Big Sandy
Big Sandy
9.4 out of 10, Exceptional, (24 reviews)
"Perfect tiny home, great location, well stocked, easy keyless entry. We enjoyed the restaurant, will book again!"
United States
Alicia B.
$136 nightly
The price is $143
Oct 12 - Oct 13
Total with taxes and fees
Cozy Tiny Home in Heart of Big Sandy
A wooden bathroom with a granite countertop, a glass bowl, a mirror, and a towel rack.

7. The Barn Loft at the Flyin H Ranch

The Barn Loft at the Flyin H Ranch
Tyler
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay!"
United States
Jessica W.
$149 nightly
The price is $155
Oct 14 - Oct 15
Total with taxes and fees
The Barn Loft at the Flyin H Ranch
A wooden cabin with a sloped roof, surrounded by tall trees.

8. The Tree House Cabin

The Tree House Cabin
Tyler
9.6 out of 10, Exceptional, (25 reviews)
"Very nice and quiet place to stay. Was as described in listing. Would stay again."
United States
Jim M.
$164 nightly
The price is $171
Oct 19 - Oct 20
Total with taxes and fees
The Tree House Cabin
A rustic wooden cabin with a kitchen featuring a stove, sink, and a clock on the wall.

9. The Lazy Squirrel Cabin

The Lazy Squirrel Cabin
Tyler
9.6 out of 10, Exceptional, (36 reviews)
"We enjoyed our stay there"
United States
Rhonda P.
$160 nightly
The price is $167
Oct 12 - Oct 13
Total with taxes and fees
The Lazy Squirrel Cabin
A bedroom with a bed, a ceiling fan, and two doors leading to other rooms.

10. woody pines 2-bedroom cabin in amazing Tyler, Texas. area with cool AC

woody pines 2-bedroom cabin in amazing Tyler, Texas. area with cool AC
tyier
$177 nightly
The price is $186
Oct 20 - Oct 21
Total with taxes and fees
woody pines 2-bedroom cabin in amazing Tyler, Texas. area with cool AC
A spacious hallway with wooden flooring, a dining area, a kitchen, and a living space.

11. Hike & Explore: 60-acre Outdoor Retreat in Tyler!

Hike & Explore: 60-acre Outdoor Retreat in Tyler!
3.0 star property
Tyler
$219 nightly
The price is $232
Oct 12 - Oct 13
Total with taxes and fees
Hike & Explore: 60-acre Outdoor Retreat in Tyler!
A rustic cabin with a wooden deck, a covered porch, and a fireplace.

12. Cora's Main Log Cabin

Cora's Main Log Cabin
Tyler
10.0 out of 10, Exceptional, (33 reviews)
"Great getaway to relax! Just a couple of minutes from Tyler State Park and fishing ponds on property!"
United States
Anonymous traveler
$210 nightly
The price is $219
Oct 20 - Oct 21
Total with taxes and fees
Cora's Main Log Cabin
A wooden deck overlooking a calm lake with trees and a clear sky.

13. Cozy Cabins in Big Sandy

Cozy Cabins in Big Sandy
Big Sandy
9.2 out of 10, Wonderful, (9 reviews)
"The cabin was super clean, the pond out front is nice and peaceful, and the restaurant across the street was both convenient and yummy."
United States
Courtney D.
$253 nightly
The price is $267
Oct 12 - Oct 13
Total with taxes and fees
Cozy Cabins in Big Sandy
A small cabin with a front porch, a door, and a window.

14. Cana Cottage

Cana Cottage
Tyler
10.0 out of 10, Exceptional, (54 reviews)
"Lovely stay, everything was perfect! Very clean, nice property. "
United States
Connor H.
$129 nightly
The price is $136
Nov 5 - Nov 6
Total with taxes and fees
Cana Cottage
A lobby with a reception desk, two sofas, a chandelier, and large windows with a view of trees and buildings.

15. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Tyler TX
10.0 out of 10, Exceptional, (108 reviews)
"Great pick if you want a place to rest after checking out Roswell."
United States
Anonymous traveler
$68 nightly
The price is $78
Oct 11 - Oct 12
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen
A neatly made bed with two pillows and two rolled towels, flanked by two bedside tables with lamps, and two framed pictures on the wall above.

16. Miranda Lambert's famous Pink Pistol is a 5-minute walk from this apartment

Miranda Lambert's famous Pink Pistol is a 5-minute walk from this apartment
Lindale
8.8 out of 10, Excellent, (5 reviews)
"Perfect little cozy spot , had everything we needed "
United States
Ryan B.
$161 nightly
The price is $169
Oct 11 - Oct 12
Total with taxes and fees
Miranda Lambert's famous Pink Pistol is a 5-minute walk from this apartment
A dining area with wooden tables and chairs, potted plants, and hanging pendant lights.

17. Tyler TX | King Bed

Tyler TX | King Bed
Tyler TX
10.0 out of 10, Exceptional, (55 reviews)
"Really enjoyed the private bathroom, totally worth it for comfort's sake!"
United States
Anonymous traveler
$72 nightly
The price is $82
Oct 11 - Oct 12
Total with taxes and fees
Tyler TX | King Bed
A modern kitchen with wooden accents, stainless steel appliances, and a dining area with a patterned rug.

18. The Texas Roost - 1-bedroom country guest house 7.4 miles to Kilgore College.

The Texas Roost - 1-bedroom country guest house 7.4 miles to Kilgore College.
Kilgore
10.0 out of 10, Exceptional, (11 reviews)
"My friend & I will definitely stay here again."
United States
Pegeen H.
$160 nightly
The price is $168
Oct 19 - Oct 20
Total with taxes and fees
The Texas Roost - 1-bedroom country guest house 7.4 miles to Kilgore College.
A cozy living room with a wooden ceiling, a television, a sofa, a coffee table, and a dining area with chairs and a table.

19. The Carriage House, The Carriage House at Jeter Farmhouse

The Carriage House, The Carriage House at Jeter Farmhouse
Gladewater
9.8 out of 10, Exceptional, (19 reviews)
"This was our second stay and again it was wonderful."
United States
Bree W.
$140 nightly
The price is $155
Oct 11 - Oct 12
Total with taxes and fees
The Carriage House, The Carriage House at Jeter Farmhouse
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

Tru by Hilton Longview

Tru by Hilton Longview

8/10 Good
"Most everything was excellent, but not having a coffee maker in the room was a bummer."
Randy 1-night trip
Posted less than an hour ago
Tru by Hilton Longview

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 $78 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?

STAY TYLER @ Faulkner- amazing location : This vacation home near Winona is located in the city center and has a patio, a barbecue grill, and air-conditioning 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 you can cook with friends or family.

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 Liberty Hall 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.