Winona Holiday Rentals

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Holiday Rentals in Winona

Cabin in the woods overlooking Grenada lake.

10.0 out of 10, Exceptional, (26)
"It was wonderful"
The price is AU$585
includes taxes & fees
27 Jan - 28 Jan
Cabin in the woods overlooking Grenada lake.

Minutes away from one of the greatest crappie fishing lakes in the world

10.0 out of 10, Exceptional, (8)
"My wife and I enjoyed our stay near Grenada Lake. The location was perfect for our getaway and the fire pit area was so peaceful. This newer cabin was cozy and comfortable. Just what we needed!"
Minutes away from one of the greatest crappie fishing lakes in the world

Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.

9.4 out of 10, Exceptional, (48)
"The owner was very good at communicating. All the places i stayed he was the one with the best hospitality! I never been to Missisippi myself my man is from there. We came for a funeral. The impression he left I will be back and most likely rent from him again. "
Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.

Homey Greenwood Getaway w/ Patio & Backyard

10.0 out of 10, Exceptional, (4)
"Not far from anything easy to get to"
Homey Greenwood Getaway w/ Patio & Backyard

The Crappie-2 bedroom cabin with spacious parking

10.0 out of 10, Exceptional, (2)
"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$503
includes taxes & fees
26 Jan - 27 Jan
The Crappie-2 bedroom cabin with spacious parking

The most unique getaway experience in North Mississippi!

10.0 out of 10, Exceptional, (2)
"Had a very nice time. Nice place to just get away and enjoy some peace"
The price is AU$451
includes taxes & fees
27 Jan - 28 Jan
The most unique getaway experience in North Mississippi!

Dogwoods-2 bedroom cabin with spacious parking

9.6 out of 10, Exceptional, (5)
"Cute well furnished cabin. Extremely clean, excellent communication with host. She went out of her way to get my favorite pjs, that I accidentally, left back to me. We saw several deer, two were just feet from the back porch. Highly recommend. Will definitely book again!!!"
The price is AU$388
includes taxes & fees
27 Jan - 28 Jan
Dogwoods-2 bedroom cabin with spacious parking

Modern Greenwood Studio < 1 Mi to Downtown!

3.0 star property
Modern Greenwood Studio < 1 Mi to Downtown!

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

10.0 out of 10, Exceptional, (9)
"Wonderful, the perfect place, just what we needed!"
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

Minutes to Grenada Lake, Restaurants, and Golf Courses.

10.0 out of 10, Exceptional, (1)
"Alvin was a great host, we ran late getting there, Alvin called to check on us. Helped with detailed instructions. Actually waited up on us past his bedtime. He was there each time we came off the lake, shared stories. He treats you in a manner that makes you relaxed and feel welcome. His location is away from traffic, yet close to docks and restaurants. Definitely consider for the peace and quiet, much preferred over hotel room. Great stay."
The price is AU$350
includes taxes & fees
26 Jan - 27 Jan
Minutes to Grenada Lake, Restaurants, and Golf Courses.

Homey Greenwood Getaway w/ Patio & Backyard

3.0 star property
Homey Greenwood Getaway w/ Patio & Backyard

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

10.0 out of 10, Exceptional, (3)
"We cannot say enough good things about this place! The rental process itself was very easy. After we had confirmed reservations, we had a couple of questions, so we sent a message to the host, and he responded much quicker than we expected. He not only answered our questions but also offered more details. The photos on VRBO are a true representation of the property – the only surprise was that the inside surpassed our expectations! It is beautifully decorated, very spacious and roomy! It was...
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit

Modern Greenwood Studio < 1 Mi to Downtown!

9.8 out of 10, Exceptional, (7)
"Very quiet and clean. The host was very respinsive."
Modern Greenwood Studio < 1 Mi to Downtown!

Greenwood Studio Cottage < 1 Mi to Downtown!

10.0 out of 10, Exceptional, (2)
"I have stayed at another one of Terra’s vacation homes before. Just like the previous home, this one did not disappoint. She was a very responsive, attentive host to all needs. The home was clean and accessible to all tourist locations. I look forward to renting from her in the future!"
Greenwood Studio Cottage < 1 Mi to Downtown!

Warm & Inviting home 5 minutes walking distance from restaurants.

8.8 out of 10, Excellent, (3)
"Conveniently located to drive to Alluvian and shopping. Nice master and dining room, also gathering room for TV. Kitchen could use a little updating, refrigerator was nice."
Warm & Inviting home 5 minutes walking distance from restaurants.

Greenwood Studio Cottage < 1 Mi to Downtown!

3.0 star property
6.8 out of 10, (3)
"Everything about this place was adorable and comfortable. The only drawback was the spotty Wi-Fi. Even after troubleshooting with the hosts it was still touchy. But overall it was an excellent stay! "
Greenwood Studio Cottage < 1 Mi to Downtown!

Updated Greenwood Cottage Apt < 1 Mi to Dtwn!

9.8 out of 10, Exceptional, (6)
"We had a sweet stay in Greenwood for a long weekend. Our biggest challenge was getting the door code sent to us, but luckily I started asking for within the last hour of our drive down. By the time we pulled into the parking space we had it and everything was good. Overall, that’s a pretty minor hiccup The neighborhood was quiet. I would not hesitate to stay again. The food in this small town rocked!!!"
Updated Greenwood Cottage Apt < 1 Mi to Dtwn!

Bream Shack-2 bedroom cabin with spacious parking

9.0 out of 10, Wonderful, (2)
"This was a great little place. The only reason it is not a full 5 stars is because the drip coffee pot had old molded coffee grounds. It was obviously an oversight by cleaning, b/c there is also a kurig there with pods, so I am sure that is what guests go to. I prefer my drip coffee, so rigged a coffee filter over the blender pitcher and boiled water on stove to make coffee. Kitchen is very well stocked. Beds were clean and comfortable. It truly is just a short drive to Grenada Lake where we...
The price is AU$450
includes taxes & fees
10 Feb - 11 Feb
Bream Shack-2 bedroom cabin with spacious parking

Catfish House-1 bedroom with spacious free parking

10.0 out of 10, Exceptional, (3)
"The place was absolutely fantastic! II would encourage anyone who needs a place to stay to make this the place! I will definetely recommend on my social platforms and will be returning in the spring for another great experience!"
The price is AU$450
includes taxes & fees
27 Jan - 28 Jan
Catfish House-1 bedroom with spacious free parking

Updated Greenwood Cottage Apt < 1 Mi to Dtwn!

3.0 star property
10.0 out of 10, Exceptional, (1)
Updated Greenwood Cottage Apt < 1 Mi to Dtwn!
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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Other types of properties in Winona you may be interested in

Holiday Inn Express and Suites Winona North, an IHG Hotel

2.5 star property
8.2 out of 10, Very good, (589)
"Very friendly staff"
The price is AU$200
includes taxes & fees
16 Feb - 17 Feb
Holiday Inn Express and Suites Winona North, an IHG Hotel

Americas Best Value Inn Winona

2.0 star property
8.0 out of 10, Very good, (375)
"i did like the fact it was cold outside and they had already turned on the heat. i didn't like the stained sofa in the room. water has to run 10 minutes before getting hott. overall nice area and staff. would recommend for future family stays"
The price is AU$146
includes taxes & fees
29 Jan - 30 Jan
Americas Best Value Inn Winona

Relax Inn & Suites

2.0 star property
5.8 out of 10, (39)
"Enjoyed my stay!"
Relax Inn & Suites
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.

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?

Cabin in the woods overlooking Grenada lake.: This holiday home rental outside Winona is located on a lake, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Winona?

Take time out to visit local sights such as Montgomery County Performing Arts Center, Middleton Cemetery, and Winona Country Club. In the wider area, you’ll also find Grenada Country Club.

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.