What are the top rated Cottage Rentals in Winona?

There are a lot of options in Winona. If you plan on staying in the Winona area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Winona: <a href="/property/kayak-walk-or-swim-to-meredith-town-center/HA-3213239542" class="class="static-page-link"">Kayak, walk or swim to Meredith town center</a> <a href="/property/meredith-modern-lakefront-4-bedroom-2-1-2-bath-home-w-beautiful-views/HA-1217523675" class="class="static-page-link"">MEREDITH MODERN LAKEFRONT 4 BEDROOM, 2 &amp; 1/2 BATH, HOME W. BEAUTIFUL VIEWS.</a> <a href="/property/meredith-new-3-bedrooms-2-1-2-baths-400yds-to-beach-1-mile-to-town-sleeps-9/HA-1214783896" class="class="static-page-link"">Meredith, New 3 Bedrooms, 2 1/2 Baths, 400Yds To Beach,1 Mile To Town Sleeps 9</a> <a href="/property/modern-lakefront-home-on-lake-waukewan-with-spectacular-fall-folliage-views/HA-121252528" class="class="static-page-link"">Modern lakefront home on Lake Waukewan with spectacular fall folliage views!</a> <a href="/property/meredith-modern-lakefront-4-bedroom-2-bath-home-close-to-downtown/HA-1214774775" class="class="static-page-link"">Meredith, Modern Lakefront 4 bedroom, 2 bath, home, close to downtown.</a> <a href="/property/meredith-modern-4-bdrm-2-bath-lakefront-home-close-to-downtown-central-air/HA-1214774779" class="class="static-page-link"">Meredith, Modern 4 bdrm, 2 bath, Lakefront home close to downtown, central air.</a> <a href="/property/6-bedroom-5-bath-modern-home-close-to-public-beach-on-2-acres-1-mile-to-town/HA-1213974592" class="class="static-page-link"">6 BEDROOM, 5 BATH, MODERN HOME CLOSE TO PUBLIC BEACH ON 2 ACRES, 1 MILE TO TOWN</a> <a href="/property/serenity-of-the-lake/HA-32127196" class="class="static-page-link"">Serenity of the Lake</a> <a href="/property/modern-lakefront-4-bdrm-3-bath-home-close-to-meredith-center-beautiful-views/HA-1214783894" class="class="static-page-link"">Modern Lakefront 4 Bdrm, 3 Bath, Home Close To Meredith Center, Beautiful Views</a> <a href="/property/uptown-charmer-meredith-near-winnipesaukee/HA-3213084508" class="class="static-page-link"">Uptown Charmer, Meredith near Winnipesaukee!</a>

How much does it cost to rent a cottage in Winona?

The average cost for a cottage rental in Winona is $468 per night. Isleofpalmsresorts has a wide list of great cottages near Winona that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Winona that allow pets?

Yes, here are the top cottage rentals in Winona that allow you to bring your pet: Walk to wedding venues, shops, dining, hiking, movies, ice cream & dog friendly. Hot Tub and Walk to Lakeside Dining Meredith Home! Meredith Inn Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home <a href="/all/usa/new-hampshire/new-hampton/winona" class="class="static-page-link"">See all pet-friendly vacation rentals in Winona on Isleofpalmsresorts</a>

Do you have any rental cottages in Winona that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Winona to find one that works for you.

Are there quality cottages in Winona that have indoor swimming pools?

As of 2026, the data from Isleofpalmsresorts shows that there are Over 84 private swimming pools or cottages with indoor pools in the Winona area along with other great amenities.

Winona Cottage Rentals By Owner

Walk to wedding venues, shops, dining, hiking, movies, ice cream & dog friendly.

From US $263

10.0 (193 Reviews)

House

Walk to wedding venues, shops, dining, hiking, movies, ice cream & dog friendly.

Air Conditioner
Parking
Pet Friendly

Winona Cottage Rentals & Holiday Homes

Find the best cottages in Winona - We found 84 exact matches

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