Search Holiday Rentals in Winona

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Winona holiday rentals

Deluxe Apartment, Non Smoking | Private kitchen | Full-sized fridge, microwave, oven, stovetop
9 Lake Street

Apartment in Wolfeboro

9 Lake Street
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is Rp2.367.108
Rp4.116.585 total
includes taxes & fees
16 Jan - 17 Jan 2026
9 Lake Street
Exterior
Cold Spring Plymouth Resort

Holiday Home in Ashland

Cold Spring Plymouth Resort
3.5 star property
9.2 out of 10, Wonderful, (167)
"The apartment was great, we enjoyed the pool, jacuzzi and sauna, and the staff were super nice!!"
United States
Jenn
The price is Rp2.219.709
Rp2.408.385 total
includes taxes & fees
14 Jan - 15 Jan 2026
Cold Spring Plymouth Resort
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

Hampton Inn & Suites Tilton

Hampton Inn & Suites Tilton

10/10 Excellent
"Clean comfy and great staff faculty! "
Tracy 1-night trip
Posted 1 day ago
Hampton Inn & Suites Tilton

Find out more about Winona

Search for holiday rentals in Winona on Expedia.co.id! You can easily find your home rentals, villas, holiday apartments in Winona using one of the methods below:

  • View our selection of featured holiday rentals in Winona
  • Use the map to find apartments and other holiday homes in the Winona neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winona while they last

Look no further and take a look at our great range of rental properties in Winona!

Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay.

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

Cold Spring Plymouth Resort: This holiday home rental outside of Winona is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. You can relax into your holiday with an outdoor tennis court and 1 hot tub.

How many holiday rentals are there in Winona?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Lake Waukewan and Winnipesaukee Playhouse.

What’s a holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals provide amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.