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Find a hotel, cabin, cottage or bed and breakfast in Ashland, Wisconsin

Ashland, Wisconsin, is a perfect Midwest destination for a romantic getaway or anniversary celebration. It offers a variety of cozy Bed and Breakfasts, hotels, and unique lodging. This town provides a classic Midwest feel with several lodging options for couples seeking a peaceful and romantic retreat.

One of the main attractions in Ashland, Wisconsin, is Chequamegon Bay on Lake Superior. There are endless opportunities for fishing, boating, and sea kayaking – and it’s not too far from Bayfield, WI, with easy access to the famed Apostle Islands National Lakeshore, either.

But vacations to Ashland, WI, are about more than just the water. The area is a haven for adventure enthusiasts, offering a variety of activities such as mountain biking, hiking, birding, and winter sports like cross-country skiing. The Northern Great Lakes Visitor Center is a must-visit, providing a fascinating insight into the region’s natural and cultural history. 

Like many Midwest destinations, events in Ashland do not disappoint. They host two major events that attract visitors – The Bay Days Festival in July features live music, food vendors, and various activities. In the fall, the WhistleStop Marathon and Half Marathon draws runners from all over, offering a scenic course along the historic railroad tracks.

There are several great Ashland restaurants to choose from to round out a perfect day in this quintessential Wisconsin town, too. Head to the Second Street Bistro for an authentic taste of northern Wisconsin. For a casual meal, enjoy the Deep Water Grille, a brewpub with rotating taps of craft beer and hearty comfort food that doesn’t disappoint. 

If you’re planning a wedding or elopement, Ashland offers beautiful outdoor locations that make for stunning wedding venues. The scenic lakeshore and parks provide a picturesque backdrop for your special day. Don’t forget about Wisconsin Bed and Breakfasts and cozy Inns in the area.

Unlike traditional hotels, these charming Midwest destinations provide intimate settings for weddings and elopements. They are also exceptional spots for busy vacations and relaxing retreats. With personalized and welcoming hospitality, they represent some of the best places to stay in the Midwest. 

Whether you’re celebrating an anniversary, planning a wedding, or simply enjoying a weekend getaway with your partner at a romantic B&B, Ashland, Wisconsin, promises a memorable experience. This lovely town caters to a variety of traveler interests, making it a versatile destination for all.

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Old Rittenhouse Inn

  • 301 Rittenhouse Avenue
    Bayfield, Wisconsin 54814
  • 715-779-5111
  • Email Us
Lodging & Dining in two Queen Anne Victorians and a private cottage. Lake Superior views, fireplaces, private baths, whirlpools. Romantic Getaways, Dinner Concerts, and Weddings. Celebrating 50 years.
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The Roost Bed and Breakfast

  • 203 North 15th Street
    Ashland, Nebraska 68003
  • 402-521-2056
  • Email Us
Sleep, Rest, Relax, Repeat. The Roost is a peaceful retreat located one block from the charm of downtown Ashland, NE.
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The Best of the Midwest!

The Midwest Association of Independent Inns was formed to help the discerning traveler find the best Bed and Breakfasts, Inns and Boutique Hotels. Our member properties are located throughout the Midwest with plans to welcome properties from all 13 Midwest states.

Our group of independent lodging properties looks forward to welcoming you to the Midwest.

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  • Welcome
  • Guides to the Midwest
    • Explore Illinois
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    • Explore Nebraska
    • Explore Wisconsin
  • Places To Stay
    • Check By Availability
    • View By State
    • View By City
    • Search By Amenity
    • View By Alphabetical List
  • About Us
    • About Our Association
    • Why B&B It
  • Gift Certificates
  • Innkeepers Corner
    • Join Our Association
    • Vendor Directory
    • Conferences & Learning
      • Overview
      • MWInns Conference & Trade Show
      • Aspiring Innkeeper Seminar
      • Conference Exhibitor Information
    • Inns For Sale
    • Inn & Potential Inn For Sale Listing
    • Room Remittance Form
  • 715-942-8180
  • info@mwinns.com