Winona Holiday Rentals

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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Holiday Rentals in Winona

Private kitchen
Charming ranch style log cabin with AC in scenic Winona
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!"
United States
Cierra O.
The price is AU$479
includes taxes & fees
22 Oct - 23 Oct
Charming ranch style log cabin with AC in scenic Winona
Property grounds
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
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. "
United States
Trey H.
The price is AU$289
includes taxes & fees
22 Oct - 23 Oct
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Interior
Charming 3-bedroom barn in quaint Winona with AC
Charming 3-bedroom barn in quaint Winona with AC
6.0 out of 10, (1)
"I had a hard time find this place, there need to be sign on old mountain road tell u how to get there. I had to clean one of the bathroom the shower was not clean. There are French door when u enter this place. There need to be some blind to the door."
United States
sherrida r.
The price is AU$673
includes taxes & fees
22 Oct - 23 Oct
Charming 3-bedroom barn in quaint Winona with AC
Fridge, microwave, oven, stovetop
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful
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. "
United States
Lee H.
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful
Fridge, microwave, oven, stovetop
Dogwoods-2 bedroom cabin with spacious parking
Dogwoods-2 bedroom cabin with spacious parking
9.6 out of 10, Exceptional, (15)
"Cabin was very clean and comfortable. We’ll be staying there again for sure."
United States
Gabe S.
The price is AU$414
includes taxes & fees
28 Oct - 29 Oct
Dogwoods-2 bedroom cabin with spacious parking
Interior
Bream Shack-2 bedroom cabin with spacious parking
Bream Shack-2 bedroom cabin with spacious parking
8.4 out of 10, Very good, (5)
"Impeccable!"
United States
Mary W.
The price is AU$505
includes taxes & fees
25 Oct - 26 Oct
Bream Shack-2 bedroom cabin with spacious parking
Apartment (0 Bedroom) | Interior
Greenwood Studio Cottage < 1 Mi to Downtown!
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,"
United States
Donald
Greenwood Studio Cottage < 1 Mi to Downtown!
Exterior
The most unique getaway experience in North Mississippi!
The most unique getaway experience in North Mississippi!
10.0 out of 10, Exceptional, (5)
"Had a very nice time. Nice place to just get away and enjoy some peace"
United States
JeMarcus Y.
The price is AU$464
includes taxes & fees
23 Oct - 24 Oct
The most unique getaway experience in North Mississippi!
Fridge, microwave, oven, stovetop
The Get-A-Way at Grenada lake
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!"
United States
John S.
The price is AU$568
includes taxes & fees
22 Oct - 23 Oct
The Get-A-Way at Grenada lake
Exterior
The Crappie-2 bedroom cabin with spacious parking
The Crappie-2 bedroom cabin with spacious parking
10.0 out of 10, Exceptional, (5)
"Second time staying! GREAT HOST"
United States
Kadeidra R.
The price is AU$524
includes taxes & fees
26 Oct - 27 Oct
The Crappie-2 bedroom cabin with spacious parking
Interior
The Bass Shack-2 bedroom cabin w spacious parking
The Bass Shack-2 bedroom cabin w spacious parking
9.8 out of 10, Exceptional, (6)
"The cabin was a perfect place for a getaway or to stay and fish the lake. The property host was very accommodating and helpful with anything we needed. Highly recommend any of her properties, we will be back!"
United States
Jordy B.
The price is AU$505
includes taxes & fees
22 Oct - 23 Oct
The Bass Shack-2 bedroom cabin w spacious parking
Exterior
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown
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! "
United States
matt t.
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown
Outdoor dining
Charming family retreat
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 "
United States
Jamaal C.
The price is AU$507
includes taxes & fees
24 Oct - 25 Oct
Charming family retreat
Interior
Secluded one bedroom cabin with large deck overlooking a wooded gully.
Secluded one bedroom cabin with large deck overlooking a wooded gully.
The price is AU$646
includes taxes & fees
22 Oct - 23 Oct
Secluded one bedroom cabin with large deck overlooking a wooded gully.
House (2 Bedrooms) | Interior
Homey Greenwood Getaway w/ Patio & Backyard
Homey Greenwood Getaway w/ Patio & Backyard
3.0 star property
Homey Greenwood Getaway w/ Patio & Backyard
Fridge, microwave, oven, stovetop
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
10.0 out of 10, Exceptional, (7)
"We came to Grenada to visit my wife's family. This was the perfect location and cabin for us. It's outside the city and a very peaceful setting. The barn was way more room than we needed. We enjoyed everything about it. "
United States
Brian M.
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
Terrace/patio
Warm & Inviting home 5 minutes walking distance from restaurants.
Warm & Inviting home 5 minutes walking distance from restaurants.
9.2 out of 10, Wonderful, (5)
"Perfect for our family - 3 adults. Communication was tops, best we’ve ever had with VRBO."
United States
Kevin M.
Warm & Inviting home 5 minutes walking distance from restaurants.
Dining
Cabin in the woods overlooking Grenada lake.
Cabin in the woods overlooking Grenada lake.
10.0 out of 10, Exceptional, (36)
"We enjoyed our stay!"
United States
Brooke B.
The price is AU$570
includes taxes & fees
22 Oct - 23 Oct
Cabin in the woods overlooking Grenada lake.
Fridge, microwave, oven, stovetop
Located 3 miles to Grenada Lake
Located 3 miles to Grenada Lake
10.0 out of 10, Exceptional, (1)
"Very Peaceful and relaxing "
United States
Steve B.
Located 3 miles to Grenada Lake
Exterior
Catch and Relax! Private Family friendly house w/ 5 acre fishing pond.
Catch and Relax! Private Family friendly house w/ 5 acre fishing pond.
2.0 star property
Catch and Relax! Private Family friendly house w/ 5 acre fishing pond.
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

Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG

10/10 Excellent
"The staff was nice but the room was filthy. The bathtub was filthy, the entire knob for"
James 2-night trip
Posted 7 days ago
Holiday Inn Express and Suites Winona North by IHG

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$289 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.