Winona Vacation Rentals

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Check prices for these dates

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

Our top choices for Winona vacation 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 CA $212
CA $249 total
includes taxes & fees
Nov 14 - Nov 15
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 CA $494
CA $559 total
includes taxes & fees
Nov 14 - Nov 15
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 CA $352
CA $417 total
includes taxes & fees
Nov 14 - Nov 15
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 CA $83
CA $97 total
includes taxes & fees
Dec 3 - Dec 4
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 CA $253
CA $455 total
includes taxes & fees
Dec 11 - Dec 12
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
A dining area with round wooden tables and chairs, a television, and potted plants.

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 CA $83
CA $97 total
includes taxes & fees
Dec 3 - Dec 4
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 CA $83
CA $97 total
includes taxes & fees
Dec 3 - Dec 4
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 CA $212
CA $479 total
includes taxes & fees
Dec 6 - Dec 7
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 CA $247
CA $428 total
includes taxes & fees
Nov 16 - Nov 17
The most unique getaway experience in North Mississippi!
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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 CA $212
CA $387 total
includes taxes & fees
Dec 6 - Dec 7
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 CA $230
CA $475 total
includes taxes & fees
Nov 14 - Nov 15
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 CA $162
CA $181 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $136
CA $208 total
includes taxes & fees
Nov 18 - Nov 19
Grenada Lake Resort Cabin # 5
A hallway with wooden doors, a metal ceiling, and a wooden floor.

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 CA $284
CA $495 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $136
CA $208 total
includes taxes & fees
Nov 13 - Nov 14
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 CA $282
CA $493 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $191
CA $428 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $534
CA $813 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $93
CA $109 total
includes taxes & fees
Dec 3 - Dec 4
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 CA $93
CA $109 total
includes taxes & fees
Dec 3 - Dec 4
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

10/10 Excellent

Nice hotel
Canada
linda
Reviewed March 15, 2023
Holiday Inn Express and Suites Winona North by IHG

Find out more about Winona

Everything you need to know about Winona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winona vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona vacation rentals we have selected for you start as low as CA $82 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 vacation 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 vacation.

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 vacation rentals in Winona?

Yes, there are vacation 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 coffeehouses 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 vacation home rentals that Winona has to offer?

Charming 3-bedroom barn in quaint Winona with AC: Visitors give good reviews to this Winona vacation home rental, which 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 vacation rentals like in Winona?

Vacation rentals are private properties you can stay in for a short or long stay in Winona. Vacation rentals provide amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.