Compare Winona Vacation Rentals

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Winona Rentals

Charming ranch style log cabin with AC in scenic Winona

Charming ranch style log cabin with AC in scenic Winona

3.83 mi from city center
$285 nightly
The price is $311 total per night
$311 total
Oct 1 - Oct 2
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
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.

3.83 mi from city center
$170 nightly
The price is $185 total per night
$185 total
Oct 1 - Oct 2
Total with taxes and fees
This vacation home is a smoke-free vacation home.
Charming 3-bedroom barn in quaint Winona with AC

Charming 3-bedroom barn in quaint Winona with AC

1.11 mi from city center
$400 nightly
The price is $436 total per night
$436 total
Oct 1 - Oct 2
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Dogwoods-2 bedroom cabin with spacious parking

Dogwoods-2 bedroom cabin with spacious parking

20.74 mi from city center
$256 nightly
The price is $269 total per night
$269 total
Oct 1 - Oct 2
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
The Crappie-2 bedroom cabin with spacious parking

The Crappie-2 bedroom cabin with spacious parking

20.74 mi from city center
$324 nightly
The price is $337 total per night
$337 total
Oct 1 - Oct 2
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Bream Shack-2 bedroom cabin with spacious parking

Bream Shack-2 bedroom cabin with spacious parking

20.79 mi from city center
$313 nightly
The price is $325 total per night
$325 total
Oct 1 - Oct 2
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities.
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown

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

2 out of 5
20.92 mi from city center
At this vacation home, guests have access to features like laundry facilities.
The most unique getaway experience in North Mississippi!

The most unique getaway experience in North Mississippi!

21 mi from city center
$285 nightly
The price is $300 total per night
$300 total
Oct 1 - Oct 2
Total with taxes and fees
This cabin features a hot tub and barbecue grills.
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake

2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake

21.45 mi from city center
$233 nightly
The price is $249 total per night
$249 total
Oct 1 - Oct 2
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful

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

25.96 mi from city center
$857 nightly
The price is $917 total per night
$917 total
Oct 4 - Oct 5
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Cabin in the woods overlooking Grenada lake.

Cabin in the woods overlooking Grenada lake.

26.22 mi from city center
$343 nightly
The price is $367 total per night
$367 total
Oct 1 - Oct 2
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Greenwood Studio Cottage < 1 Mi to Downtown!

Greenwood Studio Cottage < 1 Mi to Downtown!

3.5 out of 5
26.7 mi from city center
This apartment features free WiFi in public areas and barbecue grills. If you drive, take advantage of free offsite parking.
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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.

Winona Large Group Rentals

How to Book Vacation Rentals in Winona



🏠 What is the best price for Winona vacation rentals?

Winona vacation rentals range in price, starting at $185 per night.


🏠 What types of vacation rentals in Winona can I rent?

Orbitz offers a wide range of Winona rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Winona condo rentals.


🏠 Is it free to cancel my Winona vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Winona vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Winona. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Winona?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Winona apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Winona?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Winona package deals will get you even more savings.

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