Winona Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in 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!"
The price is NZ$522
includes taxes & fees
18 July - 19 July
Charming ranch style log cabin with AC in scenic Winona

Charming 3-bedroom barn in quaint Winona with AC

The price is NZ$733
includes taxes & fees
18 July - 19 July
Charming 3-bedroom barn in quaint Winona with AC

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 NZ$315
includes taxes & fees
18 July - 19 July
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

Located 3 miles to Grenada Lake

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

The Get-A-Way at Grenada lake

9.6 out of 10, Exceptional, (9)
"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 NZ$617
includes taxes & fees
18 July - 19 July
The Get-A-Way at Grenada lake

Dogwoods-2 bedroom cabin with spacious parking

9.4 out of 10, Exceptional, (10)
"Great weekend getaway spot"
Dogwoods-2 bedroom cabin with spacious parking

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 NZ$506
includes taxes & fees
20 July - 21 July
The most unique getaway experience in North Mississippi!

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

10.0 out of 10, Exceptional, (10)
"Nice quiet and clean location to share with family and friends"
The price is NZ$535
includes taxes & fees
20 July - 21 July
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to 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 "
Charming family retreat

Grenada Lake Resort Cabin # 5

10.0 out of 10, Exceptional, (6)
"we loved staying her. it was a perfect place to stay. cozy, comfortable, and clean. "
The price is NZ$263
includes taxes & fees
22 July - 23 July
Grenada Lake Resort Cabin # 5

Homey Greenwood Getaway w/ Patio & Backyard

10.0 out of 10, Exceptional, (4)
"Nice place to stay will definitely come back"
Homey Greenwood Getaway w/ Patio & Backyard

Bream Shack-2 bedroom cabin with spacious parking

9.6 out of 10, Exceptional, (4)
"Impeccable!"
Bream Shack-2 bedroom cabin with spacious parking

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!

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

10.0 out of 10, Exceptional, (2)
"House and property are very nice, and well maintained. The outside recreation area has everything for a great time for all ages. 100% plan on making this a yearly getaway for the family. "
The price is NZ$1,337
includes taxes & fees
21 July - 22 July
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful

Grenada Lake Resort Cabin # 2

10.0 out of 10, Exceptional, (2)
"Nice quite area cozy and rustic interior of the cabin "
The price is NZ$263
includes taxes & fees
19 July - 20 July
Grenada Lake Resort Cabin # 2

Cabin in the woods overlooking Grenada lake.

10.0 out of 10, Exceptional, (34)
"The cabin had a perfect combination of a rustic feel with great modern comfort and conveniences. "
The price is NZ$617
includes taxes & fees
22 July - 23 July
Cabin in the woods overlooking Grenada lake.

Grenada Lake Resort Cabin # 3

10.0 out of 10, Exceptional, (1)
"Very secluded"
The price is NZ$263
includes taxes & fees
18 July - 19 July
Grenada Lake Resort Cabin # 3

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 NZ$542
includes taxes & fees
20 July - 21 July
The Crappie-2 bedroom cabin with spacious parking

Grenada Lake Resort Cabin # 4

9.0 out of 10, Wonderful, (2)
"Very nice cabin although a little smaller than expected. Road into cabin could use some work."
The price is NZ$263
includes taxes & fees
8 Aug - 9 Aug
Grenada Lake Resort Cabin # 4

House Located Less Than 3 Miles of Grenada Lake

9.0 out of 10, Wonderful, (2)
"We had a wonderful stay. It was very quiet location out in the country. It was roomy with plenty of parking for the family. "
The price is NZ$1,023
includes taxes & fees
20 July - 21 July
House Located Less Than 3 Miles of Grenada Lake
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.
Save an average of 15% on thousands of hotels when you're signed in

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 City Hall, and Middleton Cemetery. Winona Country Club and Winona - Montgomery County Library 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.