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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winona holiday rentals

A wooden cabin with a balcony, surrounded by trees.

1. 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.
Winona
10.0 out of 10, Exceptional, (1 review)
"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 £135
includes taxes & fees
13 Nov - 14 Nov
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
A wooden door with two glass panels, a wreath on each, and a sign reading "1418B".

2. Charming 3-bedroom barn in quaint Winona with AC

Charming 3-bedroom barn in quaint Winona with AC
Winona
8.0 out of 10, Very good, (2 reviews)
"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 £301
includes taxes & fees
13 Nov - 14 Nov
Charming 3-bedroom barn in quaint Winona with AC
A cozy cabin interior with a wooden ceiling, a ceiling fan, a kitchen area with a refrigerator and stove, a dining area with a table and chairs, and a living room with a couch.

3. Charming ranch style log cabin with AC in scenic Winona

Charming ranch style log cabin with AC in scenic Winona
Winona
10.0 out of 10, Exceptional, (2 reviews)
"Nice, clean, comfortable cabin with everything you need. "
United States
Lee T.
The price is £223
includes taxes & fees
13 Nov - 14 Nov
Charming ranch style log cabin with AC in scenic Winona
A dining area with round wooden tables and chairs, a television, and potted plants.

4. Grenada MS | King Bed

Grenada MS | King Bed
Grenada MS
10.0 out of 10, Exceptional, (57 reviews)
"Stopped here for one night and it comfortably met all expectations."
United States
Anonymous traveller
The price is £51
includes taxes & fees
3 Dec - 4 Dec
Grenada MS | King Bed
A living room with a sectional sofa, armchairs, a coffee table, and a dining area with a table and chairs.

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

Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Grenada
9.6 out of 10, Exceptional, (16 reviews)
"The property was easy to find, very clean, and the beds were very comfortable. Great place to stay and cozy."
United States
Joahua
The price is £232
includes taxes & fees
23 Nov - 24 Nov
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
A hotel room with a bed, a desk, a chair, a television, and a window with curtains.

6. Grenada MS | King Bed Smoking

Grenada MS | King Bed Smoking
Grenada MS
10.0 out of 10, Exceptional, (48 reviews)
"Rooms had ample space for two guests, creating a very inviting atmosphere."
United States
Anonymous traveller
The price is £51
includes taxes & fees
3 Dec - 4 Dec
Grenada MS | King Bed Smoking
A spacious living room with a large flat-screen TV, comfortable seating, and a Christmas tree.

7. King Bed Accessible|Grenada MS

King Bed Accessible|Grenada MS
Grenada MS
10.0 out of 10, Exceptional, (67 reviews)
"Saw several families staying here,lots of space seemed great for everyone involved."
United States
Anonymous traveller
The price is £51
includes taxes & fees
3 Dec - 4 Dec
King Bed Accessible|Grenada MS
77f49a8d

8. The Crappie-2 bedroom cabin with spacious parking

The Crappie-2 bedroom cabin with spacious parking
Grenada
10.0 out of 10, Exceptional, (7 reviews)
"Cabin was nice clean and was so easy to check"
United States
Kathy B.
The price is £255
includes taxes & fees
15 Nov - 16 Nov
The Crappie-2 bedroom cabin with spacious parking
IMG_1772

9. The most unique getaway experience in North Mississippi!

The most unique getaway experience in North Mississippi!
Grenada
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property and view great host clean places loved it so much "
United States
Austin R.
The price is £228
includes taxes & fees
15 Nov - 16 Nov
The most unique getaway experience in North Mississippi!
fe118567

10. Dogwoods-2 bedroom cabin with spacious parking

Dogwoods-2 bedroom cabin with spacious parking
Grenada
9.6 out of 10, Exceptional, (21 reviews)
"Clean and excellent A/C even during very hot weather. Beds were comfortable. Good choice."
United States
Carol W.
The price is £207
includes taxes & fees
30 Nov - 1 Dec
Dogwoods-2 bedroom cabin with spacious parking
A living room with two black leather sofas, a patterned rug, and a dark wooden cabinet.

11. Magnolia State Winter Escape – Beautiful 3BR Family Home

Magnolia State Winter Escape – Beautiful 3BR Family Home
Grenada
9.0 out of 10, Wonderful, (11 reviews)
"The location was great and the size and space were fantastic. I will book this house again."
United States
JACQUELINE T.
The price is £253
includes taxes & fees
14 Nov - 15 Nov
Magnolia State Winter Escape – Beautiful 3BR Family Home
A covered porch with a cushioned bench and decorative pillows, a wooden railing, and a clear view of the surrounding landscape.

12. Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters

Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters
Greenwood
10.0 out of 10, Exceptional, (5 reviews)
"Great little cabin for a getaway. Quiet and secluded."
United States
Mark H.
The price is £96
includes taxes & fees
16 Nov - 17 Nov
Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters
Exterior

13. Grenada Lake Resort Cabin # 5

Grenada Lake Resort Cabin # 5
Coffeeville
9.8 out of 10, Exceptional, (7 reviews)
"we loved staying her. it was a perfect place to stay. cozy, comfortable, and clean. "
United States
Kevin
The price is £112
includes taxes & fees
15 Nov - 16 Nov
Grenada Lake Resort Cabin # 5
A wooden deck with a view of a lake, a grill, and a grill cover.

14. The Get-A-Way at Grenada lake

The Get-A-Way at Grenada lake
Grenada
9.8 out of 10, Exceptional, (21 reviews)
"Great property to stay at if you are staying or fishing in the Grenada area. "
United States
Jay R.
The price is £262
includes taxes & fees
13 Nov - 14 Nov
The Get-A-Way at Grenada lake
Exterior

15. Grenada Lake Resort Cabin # 4

Grenada Lake Resort Cabin # 4
Coffeeville
9.6 out of 10, Exceptional, (5 reviews)
"Smooth booking process. Booked within two days of our visit. Very clean. Pricing was very reasonable. The host was very communicative when I had questions before booking and had responded pretty fast. Will absolutely be saving this location for future visits."
United States
Sharon C.
The price is £112
includes taxes & fees
13 Nov - 14 Nov
Grenada Lake Resort Cabin # 4
A cozy cabin interior with a living room, a staircase, and a kitchen area.

16. Cabin in the woods overlooking Grenada lake.

Cabin in the woods overlooking Grenada lake.
Coffeeville
10.0 out of 10, Exceptional, (47 reviews)
"Great cabin with lots of room for families!"
United States
Scotty H.
The price is £259
includes taxes & fees
16 Nov - 17 Nov
Cabin in the woods overlooking Grenada lake.
A living room with a fireplace, a television, and a sofa.

17. Charming family retreat

Charming family retreat
Greenwood
9.2 out of 10, Wonderful, (5 reviews)
"Neat little town. Enjoy our stay"
United States
Robert W.
The price is £225
includes taxes & fees
16 Nov - 17 Nov
Charming family retreat
Private kitchen

18. House Located Less Than 3 Miles of Grenada Lake

House Located Less Than 3 Miles of Grenada Lake
Coffeeville
8.6 out of 10, Excellent, (4 reviews)
"Everything was wonderful!!"
United States
anna a.
The price is £424
includes taxes & fees
13 Nov - 14 Nov
House Located Less Than 3 Miles of Grenada Lake
A dining area with round wooden tables and chairs, a television, and potted plants.

19. 2 Queen Bed|Smk|Grenada MS

2 Queen Bed|Smk|Grenada MS
Grenada MS
10.0 out of 10, Exceptional, (52 reviews)
"Cozy beds and welcoming staff made our visit enjoyable. Free WiFi was an extra perk too."
United States
Anonymous traveller
The price is £58
includes taxes & fees
3 Dec - 4 Dec
2 Queen Bed|Smk|Grenada MS
A dining area with round wooden tables and chairs, a television, and potted plants.

20. Grenada MS |2 Queen Bed

Grenada MS |2 Queen Bed
Grenada MS
10.0 out of 10, Exceptional, (66 reviews)
"Quiet location made it easy to relax after busy days exploring Jackson."
United States
Anonymous traveller
The price is £58
includes taxes & fees
3 Dec - 4 Dec
Grenada MS |2 Queen Bed
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

A Holiday Inn Express hotel with a covered entrance, a brick facade, and a clear sky.
Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG
Winona

8/10 Good

Hotel required for 1 night during our trip at the Natchez Trace Parkway. This was one of 2 in area required. Nothing much around that we could find. Local KFC, Sonic or McD's. After driving for 5 hrs that was close. Check in was a joke. Guy on reception kept shaking head saying no booking. Then once he found it kept wandering off to managers office with my passport. Then our room backed onto the lift. Breakfast was the best choice free buffet during this trip. Maybe more hot choice as pancake...
United Kingdom
JOHN
Reviewed October 6, 2017
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, apart-hotels, 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 favorite 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 depends 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 £51 per night. Entering your travel dates in the search wizard you might find 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 in Winona close to Montgomery County Performing Arts Center, 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 offers a balcony, a selection of games and air conditioning 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, Middleton Cemetery, and Winona Country Club. Winona - Montgomery County Library and Winona City Hall 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.