Chequamegon Bay Luxury Holidays

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All you need to know about luxury holidays in Chequamegon Bay

What can I expect from a luxury Chequamegon Bay holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Chequamegon Bay?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Chequamegon Bay holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Chequamegon Bay?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Chequamegon Bay starting at . Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Chequamegon Bay?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Chequamegon Bay spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Chequamegon Bay?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Chequamegon Bay?

You can wangle a top-notch luxury holiday in Chequamegon Bay for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Chequamegon Bay with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Chequamegon Bay with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Chequamegon Bay to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

Top Luxury Chequamegon Bay Hotels

Super 8 by Wyndham Ashland

Super 8 by Wyndham Ashland

2 out of 5
1610 Lake Shore Dr W, Ashland, WI
  • 12 min drive from Houghton Falls Nature Preserve
Stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,003 reviews)
"Room was clean and comfortable, nice town."

Reviewed on 15 Aug 2025

Super 8 by Wyndham Ashland
Best Western The Hotel Chequamegon

Best Western The Hotel Chequamegon

3 out of 5
101 Lake Shore Dr W, Ashland, WI
  • 12 min drive from Houghton Falls Nature Preserve
Stay at this 3-star business-friendly hotel in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the property ...
8.4/10 Very Good! (1,002 reviews)
"It is a great hotel with amazing views of the bay from your window. Balcony and outside seating to enjoy the boats and to enjoy a meal or drinks. The best breakfast above and beyond other hotels."

Reviewed on 15 Aug 2025

Best Western The Hotel Chequamegon
AmericInn by Wyndham Ashland

AmericInn by Wyndham Ashland

2.5 out of 5
3009 Lakeshore Drive East, Ashland, WI
  • 14 min drive from Houghton Falls Nature Preserve
Stay at this beach hotel in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. Popular ...
7.8/10 Good! (1,003 reviews)
"Our bathroom ceiling had a slow water drip above the toilet. We called maintenance and they fixed it quickly."

Reviewed on 15 Aug 2025

AmericInn by Wyndham Ashland
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.