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Winona Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winona vacation rentals

A row of brown single-story buildings with a parking lot in front.

1. Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (276 reviews)
"Had a great weekend stay."
United States
Armand
$148 nightly
The price is $161
Nov 1 - Nov 2
Total with taxes and fees
Cold Spring Plymouth Resort
A cozy living room with a brown leather sofa, a wooden coffee table, and a fish-themed wall decoration.

2. Lake Winnipesaukee Home for Fall & Winter Fun

Lake Winnipesaukee Home for Fall & Winter Fun
3.0 star property
Moultonborough
$422 nightly
The price is $458
Oct 13 - Oct 14
Total with taxes and fees
Lake Winnipesaukee Home for Fall & Winter Fun
A spacious kitchen with wooden beams, a large dining table, and a fireplace.

3. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
3.0 star property
Tuftonboro
10.0 out of 10, Exceptional, (2 reviews)
"We’ll kept "
United States
Denise
$426 nightly
The price is $462
Oct 12 - Oct 13
Total with taxes and fees
Cozy Tuftonboro Escape: Steps to Private Beaches!
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

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

10/10 Excellent
"Our stay at the Tilton Holiday Inn Express was very nice. It is a clean hotel with a good continental breakfast. The beds were comfortable and the iron and ironing board worked well. The towels are a little thin, but other than that everything about the room was fine."
Heather 2-night trip
Posted 2 hours ago
Holiday Inn Express Hotel & Suites Tilton - Lakes Region 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, 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 $161 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.

Frequently asked questions

Are there vacation rentals in Winona?

Yes, we have vacation rentals close to top sights in Winona, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Winona has to offer?

Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.: This vacation home rental outside of Winona is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winona?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Winona stay.

What’s there to see and do in Winona?

Explore the area and family-friendly sights such as Squam Lakes Natural Science Center, or get out into nature at a spot like Winona Lake. In the larger area, you’ll find Lake Waukewan and Barnz's Meredith Cinema.

What’s a vacation rental in Winona like?

Vacation rentals are private properties you can stay in for short or long periods in Winona. Vacation rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.