Holiday Rentals in Winona

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Holiday Rentals in Winona

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

9.4 out of 10, Exceptional, (47)
"Grenada is halfway between all our kids. This was a great place for all of to meet for the long weekend. Convenient to town and the lake. "
Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.

Spacious Grenada Brick Home: Perfect Fall Escape. Close to Downtown

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great atmosphere and great area near downtown Grenada..."
Spacious Grenada Brick Home: Perfect Fall Escape. Close to Downtown

The most unique getaway experience in North Mississippi!

The price is €276
includes taxes & fees
25 Dec - 26 Dec
The most unique getaway experience in North Mississippi!

Cabin in the woods overlooking Grenada lake.

10.0 out of 10, Exceptional, (26)
"It was wonderful"
The price is €357
includes taxes & fees
5 Jan - 6 Jan 2025
Cabin in the woods overlooking Grenada lake.

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

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!"
The price is €236
includes taxes & fees
26 Dec - 27 Dec
Minutes away from one of the greatest crappie fishing lakes in the world

The Get-A-Way at Grenada lake

10.0 out of 10, Exceptional, (2)
"This place was Great ! Great location great atmosphere and adorable on the inside . Not to mention there was a pond you could fish in . The kids loved it as well! And an amazing shower."
The price is €358
includes taxes & fees
24 Dec - 25 Dec
The Get-A-Way at Grenada lake

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!"
The price is €281
includes taxes & fees
28 Dec - 29 Dec
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 €211
includes taxes & fees
24 Dec - 25 Dec
Minutes to Grenada Lake, Restaurants, and Golf Courses.

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 €309
includes taxes & fees
24 Dec - 25 Dec
The Crappie-2 bedroom cabin with spacious parking

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...
The price is €561
includes taxes & fees
5 Jan - 6 Jan 2025
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit

Dogwoods-2 bedroom cabin with spacious parking

9.6 out of 10, Exceptional, (4)
"I was very impressed with this cabin. We were visiting family in the area and we like to have our on space to retreat to at the end of the day and this cabin fit the bill. Everything was very clean and well maintained. Kitchen included all needed pots and utensils for cooking simple meals. The road getting to the cabin is steep when coming off of the main road which makes it easy to miss. The bathroom plumbing needs some work. The toilet bubbles when the washing machine is on. The shower needs...
The price is €237
includes taxes & fees
24 Dec - 25 Dec
Dogwoods-2 bedroom cabin with spacious parking

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, (1)
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...
Bream Shack-2 bedroom cabin with spacious parking
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, (578)
"Great"
The price is €123
includes taxes & fees
29 Dec - 30 Dec
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, (370)
"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 €84
includes taxes & fees
24 Dec - 25 Dec
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?

Spacious Grenada Brick Home: Perfect Fall Escape. Close to Downtown: This holiday home rental outside Winona is equipped with a selection of games, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.