A brick building with the inscription "WINONA" and an arched window.

Winona Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Winona vacation rentals

Exterior

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.
$171 nightly
The price is $186
Jul 17 - Jul 18
Total with taxes and fees
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Exterior detail

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.
$400 nightly
The price is $436
Jul 22 - Jul 23
Total with taxes and fees
Charming 3-bedroom barn in quaint Winona with AC
Exterior

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
$146 nightly
The price is $156
Jul 20 - Jul 21
Total with taxes and fees
Grenada Lake Resort Cabin # 5
Exterior

Grenada Lake Resort Cabin # 3

Grenada Lake Resort Cabin # 3
Coffeeville
10.0 out of 10, Exceptional, (1 review)
"Very secluded"
United States
Connie B.
$146 nightly
The price is $156
Jul 17 - Jul 18
Total with taxes and fees
Grenada Lake Resort Cabin # 3
Terrace/patio

Dogwoods-2 bedroom cabin with spacious parking

Dogwoods-2 bedroom cabin with spacious parking
Grenada
9.6 out of 10, Exceptional, (17 reviews)
"Cabin was very clean and comfortable. We’ll be staying there again for sure."
United States
Gabe S.
$276 nightly
The price is $289
Jul 19 - Jul 20
Total with taxes and fees
Dogwoods-2 bedroom cabin with spacious parking
Terrace/patio

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, (4 reviews)
"Great little cabin for a getaway. Quiet and secluded."
United States
Mark H.
$128 nightly
The price is $137
Jul 20 - Jul 21
Total with taxes and fees
Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters
Interior

Minutes away from one of the greatest crappie fishing lakes in the world

Minutes away from one of the greatest crappie fishing lakes in the world
Coffeeville
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay and great host! "
United States
Josh P.
$226 nightly
The price is $242
Jul 19 - Jul 20
Total with taxes and fees
Minutes away from one of the greatest crappie fishing lakes in the world
TV

The Crappie-2 bedroom cabin with spacious parking

The Crappie-2 bedroom cabin with spacious parking
Grenada
10.0 out of 10, Exceptional, (6 reviews)
"Second time staying! GREAT HOST"
United States
Kadeidra R.
$340 nightly
The price is $353
Jul 19 - Jul 20
Total with taxes and fees
The Crappie-2 bedroom cabin with spacious parking
Exterior detail

King Bed Accessible|Grenada MS

King Bed Accessible|Grenada MS
Grenada MS
10.0 out of 10, Exceptional, (67 reviews)
"Rates felt very reasonable given the amenities. Glad I picked this place over others nearby."
United States
Anonymous traveler
$89 nightly
The price is $97
Aug 9 - Aug 10
Total with taxes and fees
King Bed Accessible|Grenada MS
Dining

Grenada MS | King Bed

Grenada MS | King Bed
Grenada MS
10.0 out of 10, Exceptional, (57 reviews)
"Discovered this peaceful place to spend the night. It was nice to unwind and take it easy here."
United States
Anonymous traveler
$89 nightly
The price is $97
Aug 9 - Aug 10
Total with taxes and fees
Grenada MS | King Bed
Dining

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 traveler
$89 nightly
The price is $97
Aug 9 - Aug 10
Total with taxes and fees
Grenada MS | King Bed Smoking
Property grounds

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.
$304 nightly
The price is $319
Jul 19 - Jul 20
Total with taxes and fees
The most unique getaway experience in North Mississippi!
Property grounds

Secluded one bedroom cabin with large deck overlooking a wooded gully.

Secluded one bedroom cabin with large deck overlooking a wooded gully.
Grenada
$413 nightly
The price is $431
Jul 19 - Jul 20
Total with taxes and fees
Secluded one bedroom cabin with large deck overlooking a wooded gully.
Interior

Bream Shack-2 bedroom cabin with spacious parking

Bream Shack-2 bedroom cabin with spacious parking
Grenada
8.4 out of 10, Very Good, (5 reviews)
"Impeccable!"
United States
Mary W.
$330 nightly
The price is $342
Aug 2 - Aug 3
Total with taxes and fees
Bream Shack-2 bedroom cabin with spacious parking
Exterior

Grenada Lake Resort Cabin # 4

Grenada Lake Resort Cabin # 4
Coffeeville
9.4 out of 10, Exceptional, (3 reviews)
"Very nice cabin although a little smaller than expected. Road into cabin could use some work."
United States
Annette J.
$146 nightly
The price is $156
Jul 17 - Jul 18
Total with taxes and fees
Grenada Lake Resort Cabin # 4
Smart TV

Cabin in the woods overlooking Grenada lake.

Cabin in the woods overlooking Grenada lake.
Coffeeville
10.0 out of 10, Exceptional, (43 reviews)
"It was amazing and we will be coming back!"
United States
Elisha B.
$342 nightly
The price is $366
Aug 3 - Aug 4
Total with taxes and fees
Cabin in the woods overlooking Grenada lake.
Exterior

Grenada Lake Resort Cabin # 2

Grenada Lake Resort Cabin # 2
Coffeeville
10.0 out of 10, Exceptional, (2 reviews)
"Nice quite area cozy and rustic interior of the cabin "
United States
James
$146 nightly
The price is $156
Jul 19 - Jul 20
Total with taxes and fees
Grenada Lake Resort Cabin # 2
Exterior

Grenada Lake Resort Cabin # 1

Grenada Lake Resort Cabin # 1
Coffeeville
10.0 out of 10, Exceptional, (3 reviews)
"Great for peace and quiet"
United States
Summer
$146 nightly
The price is $156
Jul 17 - Jul 18
Total with taxes and fees
Grenada Lake Resort Cabin # 1
Smart TV

Magnolia State Winter Escape – Beautiful 3BR Family Home

Magnolia State Winter Escape – Beautiful 3BR Family Home
Grenada
9.2 out of 10, Wonderful, (9 reviews)
"Great atmosphere and great area near downtown Grenada..."
United States
Lelabug G.
$331 nightly
The price is $354
Jul 17 - Jul 18
Total with taxes and fees
Magnolia State Winter Escape – Beautiful 3BR Family Home
Smart TV, fireplace, DVD player, books

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
10.0 out of 10, Exceptional, (14 reviews)
"Nice quiet and clean location to share with family and friends"
United States
Janet T.
$315 nightly
The price is $337
Aug 3 - Aug 4
Total with taxes and fees
Lida's Place - 3 BR 2 BA Ranch House - 7.6 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winona Hotel Reviews

Americas Best Value Inn Winona

Americas Best Value Inn Winona

10/10 Excellent
"We loved our stay we will be stay again next time we go to mississippi"
Elizabeth 3-night trip
Posted 4 hours ago
Americas Best Value Inn Winona

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $137 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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