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Top 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 £230
includes taxes & fees
9 Jul - 10 Jul
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 £137
includes taxes & fees
9 Jul - 10 Jul
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 £323
includes taxes & fees
9 Jul - 10 Jul
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 £224
includes taxes & fees
9 Jul - 10 Jul
The most unique getaway experience in North Mississippi!

The Crappie-2 bedroom cabin with spacious parking

10.0 out of 10, Exceptional, (4)
"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 £239
includes taxes & fees
9 Jul - 10 Jul
The Crappie-2 bedroom cabin with spacious parking

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 £273
includes taxes & fees
5 Jul - 6 Jul
Cabin in the woods overlooking Grenada lake.

Grenada Lake Resort Cabin # 4

10.0 out of 10, Exceptional, (1)
"We had a last minute booking this cabin for one night. We were pleased based on our basic needs for one night. "
The price is £116
includes taxes & fees
9 Jul - 10 Jul
Grenada Lake Resort Cabin # 4

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 £116
includes taxes & fees
9 Jul - 10 Jul
Grenada Lake Resort Cabin # 5

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

2.0 star property
9.2 out of 10, Wonderful, (5)
"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

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 £236
includes taxes & fees
8 Jul - 9 Jul
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

Bream Shack-2 bedroom cabin with spacious parking

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

Dogwoods-2 bedroom cabin with spacious parking

9.6 out of 10, Exceptional, (9)
"Great cabin close to the lake and easy access to town. Except for the fact that we didn’t catch any fish, and it rained, it was a fun trip. Only negative I could find….single ply toilet paper. Haha, but seriously, it’s a great place and the hosts are excellent to work with. "
The price is £185
includes taxes & fees
9 Jul - 10 Jul
Dogwoods-2 bedroom cabin with spacious parking

Grenada Lake Resort 2 bedroom Cabin # 6

9.4 out of 10, Exceptional, (3)
"This place is outstanding! It's priced well and offers all the amenities for a comfortable stay. I will definitely be coming back."
The price is £185
includes taxes & fees
9 Jul - 10 Jul
Grenada Lake Resort 2 bedroom Cabin # 6

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

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!

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 £116
includes taxes & fees
27 Jul - 28 Jul
Grenada Lake Resort Cabin # 2

Located 3 miles to Grenada Lake

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

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 £452
includes taxes & fees
9 Jul - 10 Jul
House Located Less Than 3 Miles of Grenada Lake

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 £187
includes taxes & fees
27 Jun - 28 Jun
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to 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.
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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 Country Club, and Winona - Montgomery County Library. In the wider area, you’ll find Winona City Hall and Middleton Cemetery.

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.