Winona Holiday Rentals

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Holiday Rentals in Winona

Our top choices for Winona holiday rentals

Charming ranch style log cabin with AC in scenic Winona

10.0 out of 10, Exceptional, (1)
"First time staying in a cabin and was absolutely impressed! It was such a peaceful stay especially coming from being in the daily city life! David was awesome at communicating. Will be reserving again for sure!"
The price is AU$470
includes taxes & fees
7 Oct - 8 Oct
Charming ranch style log cabin with AC in scenic Winona

Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

10.0 out of 10, Exceptional, (1)
"This is a cute little rustic cabin. Chad was very friendly and open to suggestions due to being a first time host. "
The price is AU$286
includes taxes & fees
7 Oct - 8 Oct
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

Charming 3-bedroom barn in quaint Winona with AC

The price is AU$660
includes taxes & fees
7 Oct - 8 Oct
Charming 3-bedroom barn in quaint Winona with AC

The most unique getaway experience in North Mississippi!

10.0 out of 10, Exceptional, (3)
"Had a very nice time. Nice place to just get away and enjoy some peace"
The price is AU$467
includes taxes & fees
7 Sept - 8 Sept
The most unique getaway experience in North Mississippi!

Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown

2.0 star property
9.4 out of 10, Exceptional, (6)
"It was very nice stay, it’s the nicest house in the area! A lot of parking! "
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown

4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful

10.0 out of 10, Exceptional, (2)
"Amazing home and outdoor patio with pool! This place is beautiful and very close to Grenada Lake boat launch. "
The price is AU$1,423
includes taxes & fees
7 Sept - 8 Sept
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful

Cabin in the woods overlooking Grenada lake.

10.0 out of 10, Exceptional, (36)
"We enjoyed our stay!"
The price is AU$570
includes taxes & fees
8 Sept - 9 Sept
Cabin in the woods overlooking Grenada lake.

Greenwood Studio Cottage < 1 Mi to Downtown!

3.5 star property
6.8 out of 10, (3)
"Every thing was great except the bed mattress was very uncomfortable, and the door to the bathroom was sticking when you open and closed it. Overall iitwas an excellent stay,"
Greenwood Studio Cottage < 1 Mi to Downtown!

Bream Shack-2 bedroom cabin with spacious parking

8.4 out of 10, Very good, (5)
"Impeccable!"
The price is AU$509
includes taxes & fees
7 Sept - 8 Sept
Bream Shack-2 bedroom cabin with spacious parking

The Crappie-2 bedroom cabin with spacious parking

10.0 out of 10, Exceptional, (5)
"This was the perfect private family-friendly spot, especially traveling from Texas to visit family when you're not familiar with the area. The host was responsive and considerate, ensuring our stay was comfortable from start to finish."
The price is AU$527
includes taxes & fees
7 Sept - 8 Sept
The Crappie-2 bedroom cabin with spacious parking

Dogwoods-2 bedroom cabin with spacious parking

9.4 out of 10, Exceptional, (13)
"Quick overnight stay for fishing trip everything was great, The only complaint was it seemed there something on the sheets in queen bed."
The price is AU$413
includes taxes & fees
7 Sept - 8 Sept
Dogwoods-2 bedroom cabin with spacious parking

The Get-A-Way at Grenada lake

9.8 out of 10, Exceptional, (12)
"Great place to stay for a fishing getaway ,close to the lake and not far from town . Owner was very responsive to my text , love that you can back your boats up under the shelter will definitely stay here again if we come down again!"
The price is AU$570
includes taxes & fees
7 Sept - 8 Sept
The Get-A-Way at Grenada lake

Charming family retreat

10.0 out of 10, Exceptional, (1)
"If u really wanted stay in the heart of greenwood it’s the perfect place to stay every thing about this house is perfect "
The price is AU$528
includes taxes & fees
8 Sept - 9 Sept
Charming family retreat

Located 3 miles to Grenada Lake

10.0 out of 10, Exceptional, (1)
"Very Peaceful and relaxing "
Located 3 miles to Grenada Lake

Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

10.0 out of 10, Exceptional, (11)
"Nice quiet and clean location to share with family and friends"
The price is AU$523
includes taxes & fees
7 Oct - 8 Oct
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit

10.0 out of 10, Exceptional, (7)
"Our stay was shorter than what we expected, but everything was just perfect"
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit

Homey Greenwood Getaway w/ Patio & Backyard

3.0 star property
Homey Greenwood Getaway w/ Patio & Backyard

2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake

10.0 out of 10, Exceptional, (1)
"THE CABIN WAS AMAZING!! THE VEIWS FROM THE BACK PORCH WAS ABSOLUTELY BREATH TAKING!THE CABIN WAS VERY NICE AND CLEAN. CAN'T WAIT TO GO BACK!"
The price is AU$383
includes taxes & fees
16 Sept - 17 Sept
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake

Updated Greenwood Cottage Apt < 1 Mi to Dtwn!

3.0 star property
10.0 out of 10, Exceptional, (2)
"We can't say enough positive about the property and especially the manager/owner. The property is an updated apartment for sure. Clean, well equipped, and spacious. She texted us twice in our four night stay to make sure everything was going well. We highly recommend this property!!! Thank you!!"
Updated Greenwood Cottage Apt < 1 Mi to Dtwn!

The Postmaster's Quarters at 2nd & Main - 2 story apartment in the historic district

9.8 out of 10, Exceptional, (7)
"Beautifully decorated, spacious, quiet getaway from the bustling metropolis I call home. Owner was friendly and responsive! "
The Postmaster's Quarters at 2nd & Main - 2 story apartment in the historic district
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

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winona holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as AU$286 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday 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 holiday.

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 holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay. Winona is known for its coffee shops and baseball games. Make sure you have time to check out the restaurants while you're in the area.

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

Charming 3-bedroom barn in quaint Winona with AC: This highly rated holiday home rental in Winona has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Winona?

Take time out to visit local sights such as Montgomery County Performing Arts Center, Winona - Montgomery County Library, and Middleton Cemetery. Winona City Hall and Winona Country Club are other places to visit while you're in town.

What are holiday rentals like in Winona?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winona. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge 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 is another reason why a holiday rental is a popular option for a family trip.