Downtown Windermere, Great

Discover shopping, dining, and accommodation in downtown Windermere.

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Hotels

Hotel Tips

Most hotel offer a complimentary breakfast bar or even a full cafe meal with your choice of a full menu. Keep in mind that some offer nothing at all so it is a good idea to pack a few packets of instant oatmeal for a quick and easy meal before you head out for the day.

Always find a reason to email the front desk manager in hotels that you plan to visit again. Tell them what they did right and express your plans to stay again and ask what opportunities there might be for frequent discounts or upgrades on your next visits. If you become friends with the manager, you just might get the friends and family rate some day.

Call ahead to make sure your reservation is still active and rebook if there are any price drops or changes in number of people staying with you. Another cost saving tips is to bundle the stay with airport parking and shuttle to avoid hefty fees.

Things To Do

Windermere brings smiles by way of doughnuts and pastries made fresh daily for your enjoyment. Everyone has their favorite of course but having a variety of bakeries is what makes downtown so special. Fritters, scones and pies oh my!

Windermere brings meaning to leisure time while enjoying the local yarn shop and wandering through in amazement with the different fibers and vast array of colors. Signing up for a class is easy and fun and serves as a great getaway for a few hours to enjoy the company of fellow knitters.

Windermere gives several options to find the right piece of art as it takes time and a diligent effort to get just the right piece. Shopping for art downtown is the best way to locate your next purchase.

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Why Do You Love Downtown?

Stephanie Seavers

Close to work but also love all the small business owners, friendliness and just how supporting our local area makes me feel!

Mike Adamski

Love shopping for unique finds and supporting local shops!

Kimberly Turner

We love to vacation and visit downtown.

CJ

Great vibe to this town! My mom lives in Medford so when I come to visit, I like to stop in Ashland.

heather ashbaker

this will be my first visit

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