Winona Vacation Rentals

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Our top choices for Winona vacation rentals

Relaxing Country Stay with Events Welcome!

Relaxing Country Stay with Events Welcome!
Winona
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
Jan 11 - Jan 12
Total with taxes and fees
Relaxing Country Stay with Events Welcome!

Chic Suite in Central Longview King Bed

Chic Suite in Central Longview King Bed
Longview
10.0 out of 10, Exceptional, (21)
"Loved the loft- clean and secure. "
United States
Jessica H.
$226 nightly
The price is $256
Jan 10 - Jan 11
Total with taxes and fees
Chic Suite in Central Longview King Bed

Cozy cabin in charming Hawkins with AC

Cozy cabin in charming Hawkins with AC
Hawkins
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.
$110 nightly
The price is $122
Jan 10 - Jan 11
Total with taxes and fees
Cozy cabin in charming Hawkins with AC

The Cottage at Dogwood Ridge.

The Cottage at Dogwood Ridge.
Whitehouse
10.0 out of 10, Exceptional, (110)
"Absolutely loved this place! So peaceful and serene. "
United States
Amy
$160 nightly
The price is $168
Jan 11 - Jan 12
Total with taxes and fees
The Cottage at Dogwood Ridge.

Cana Cottage | Farm Stay

Cana Cottage | Farm Stay
Tyler
10.0 out of 10, Exceptional, (44)
"Good design, well maintained "
United States
William
$112 nightly
The price is $118
Jan 14 - Jan 15
Total with taxes and fees
Cana Cottage | Farm Stay

Cora's Cabins

Cora's Cabins
3.0 star property
Tyler
9.4 out of 10, Exceptional, (157)
"Enjoyed the stay "
United States
Benito
$142 nightly
The price is $149
Jan 14 - Jan 15
Total with taxes and fees
Cora's Cabins

Home away from Home- Near Tyler Airport

Home away from Home- Near Tyler Airport
Tyler
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
Jan 10 - Jan 11
Total with taxes and fees
Home away from Home- Near Tyler Airport

The Happy Pine Cone :)

The Happy Pine Cone :)
Tyler
9.8 out of 10, Exceptional, (37)
"Very cute little cabin"
United States
David s.
$145 nightly
The price is $151
Jan 12 - Jan 13
Total with taxes and fees
The Happy Pine Cone :)

The Skelly Hideout

The Skelly Hideout
Kilgore
10.0 out of 10, Exceptional, (2)
"Will definitely be staying again . Quiet area ;)"
United States
Dreamy Y.
$205 nightly
The price is $216
Jan 11 - Jan 12
Total with taxes and fees
The Skelly Hideout

The Tree House Cabin

The Tree House Cabin
Tyler
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
Jan 12 - Jan 13
Total with taxes and fees
The Tree House Cabin

Cozy Wood Cottage in Tyler

Cozy Wood Cottage in Tyler
2.0 star property
Tyler
8.8 out of 10, Excellent, (3)
"The host was very accommodating and understanding. "
United States
Mindy M.
$110 nightly
The price is $115
Jan 10 - Jan 11
Total with taxes and fees
Cozy Wood Cottage in Tyler

The Lazy Squirrel Cabin

The Lazy Squirrel Cabin
Tyler
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
Jan 11 - Jan 12
Total with taxes and fees
The Lazy Squirrel Cabin

Cozy Tiny Home in Heart of Big Sandy

Cozy Tiny Home in Heart of Big Sandy
Big Sandy
9.4 out of 10, Exceptional, (23)
"Very nuce perfect size for just the husband and I. Could have used just a little more privacy in the front sitting area oitside. But overall, great experience. "
United States
Jennifer W.
$136 nightly
The price is $143
Jan 10 - Jan 11
Total with taxes and fees
Cozy Tiny Home in Heart of Big Sandy

Guesthouse on peaceful 11+ acre homestead! Pet friendly!

Guesthouse on peaceful 11+ acre homestead! Pet friendly!
Tyler
10.0 out of 10, Exceptional, (35)
"The place is beautiful and peaceful. Very private and was a bonus to have my dog with me! "
United States
Ginger M.
$124 nightly
The price is $130
Jan 12 - Jan 13
Total with taxes and fees
Guesthouse on peaceful 11+ acre homestead! Pet friendly!

Charming 3-bedroom house on quiet street in delightful Kilgore

Charming 3-bedroom house on quiet street in delightful Kilgore
Kilgore
9.4 out of 10, Exceptional, (3)
"Clean home, excellent host"
United States
Ashley S.
$203 nightly
The price is $214
Jan 11 - Jan 12
Total with taxes and fees
Charming 3-bedroom house on quiet street in delightful Kilgore

The Carriage House, The Carriage House at Jeter Farmhouse

The Carriage House, The Carriage House at Jeter Farmhouse
Gladewater
9.6 out of 10, Exceptional, (10)
"Very nice rental "
United States
michael S.
$129 nightly
The price is $135
Jan 15 - Jan 16
Total with taxes and fees
The Carriage House, The Carriage House at Jeter Farmhouse

The Floret Cottage

The Floret Cottage
TYLER
10.0 out of 10, Exceptional, (2)
"Great location! We enjoyed the wonderful amenities and personal care services offered! "
United States
Kimberly G.
$280 nightly
The price is $295
Jan 11 - Jan 12
Total with taxes and fees
The Floret Cottage

Charming Home in the Piney Woods of East Texas

Charming Home in the Piney Woods of East Texas
Kilgore
9.4 out of 10, Exceptional, (17)
"This property is a blessing for guest. "
United States
michael t.
$236 nightly
The price is $249
Jan 10 - Jan 11
Total with taxes and fees
Charming Home in the Piney Woods of East Texas
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

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 $115 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.

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 @ Parade of Homes : This vacation home rental near Winona offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable 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 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.