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Featured Chequamegon Bay Family Hotels

Best Western The Hotel Chequamegon
101 Lake Shore Dr W, Ashland, WI
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...

AmericInn by Wyndham Ashland
3009 Lakeshore Drive East, Ashland, WI
Fully refundableReserve now, pay when you stay
Book a stay at this beach hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...

Super 8 by Wyndham Ashland
1610 Lake Shore Dr W, Ashland, WI
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Quality Inn Ashland - Lake Superior
30600 Us Highway 2, Ashland, WI
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

Mission Springs Lake House
30190 Mission Springs Road, Ashland, WI
Stay at this 3-star beach cottage in Ashland. Enjoy free WiFi, free parking, and a private beach. Popular attractions Northern Great Lakes Visitor Center and ...

The Washburn Inn - On the Lake
123 Harbor View Drive, Washburn, WI
Fully refundableReserve now, pay when you stay
Book a stay at this golf hotel in Washburn. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms ...
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.
Hotels with Pools in Chequamegon Bay

Super 8 by Wyndham Ashland
1610 Lake Shore Dr W, Ashland, WI
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,010 reviews)
"Breakfast was great"
Reviewed on Sep 19, 2025

Quality Inn Ashland - Lake Superior
30600 Us Highway 2, Ashland, WI
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (887 reviews)
"Beautiful view of Lake Superior. Nice breakfast"
Reviewed on Sep 22, 2025

AmericInn by Wyndham Ashland
3009 Lakeshore Drive East, Ashland, WI
Book a stay at this beach hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
7.8/10 Good! (1,005 reviews)
America Matters So Let's Show That It Does
"It is a hidden gem with exceptional staff. They are doing their best to stay afloat like too many places are. The building is aged yet they do their best with what they can. The necessity of fresh linens and towels. The renovation of their breakfast area was a hidden gem with still fresh waffle toppings, ..."
Reviewed on Sep 23, 2025
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.
Hotels With Connecting Rooms in Chequamegon Bay

AmericInn by Wyndham Ashland
3009 Lakeshore Drive East, Ashland, WI
Book a stay at this beach hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...

Best Western The Hotel Chequamegon
101 Lake Shore Dr W, Ashland, WI
Stay at this 3-star business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...

Super 8 by Wyndham Ashland
1610 Lake Shore Dr W, Ashland, WI
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.
Hotels by Star Rating
More Hotel Options
- Hotels with Free Parking in Chequamegon Bay
- Beach Hotels in Chequamegon Bay
- Hotels with a Pool in Chequamegon Bay
- Hotels with Hot Tubs in Chequamegon Bay
- Romantic Hotels in Chequamegon Bay
- Hotels with an Indoor Pool in Chequamegon Bay
- Pet-friendly Hotels in Chequamegon Bay
- Historic Hotels in Chequamegon Bay
- Resorts & Hotels with Spas in Chequamegon Bay
- Luxury Hotels in Chequamegon Bay
Top Points of Interests in Chequamegon Bay
- Hotels near Houghton Falls Nature Preserve
- Hotels near Chequamegon Bay Golf Course
- Hotels near Ashland Historical Museum
- Hotels near Ashland Mural Walk
- Hotels near Bayfield County Courthouse
- Hotels near Soo Line Locomotive 950
- Hotels near Bayview Park
- Hotels near Ore Dock Park
- Hotels near StageNorth
- Hotels near Apostle Islands Marina
- Hotels near Apostle Islands Mainland Sea Caves
- Hotels near Madeline Island Ferry Line
- Hotels near Copper Falls State Park
- Hotels near Apostle Islands Cruises
- Hotels near Chequamegon National Forest
- Hotels near Madeline Island Museum
- Hotels near Legendary Waters Casino
- Hotels near Potato River Falls
- Hotels near Northern Great Lakes Visitor Center
Cities near Chequamegon Bay
- Bayfield Hotels (10.51 mi)
- Upper Peninsula Hotels (163.6 mi)
- Ashland Hotels (5.08 mi)
- Ironwood Hotels (34.84 mi)
- Washburn Hotels (2.81 mi)
- Cable Hotels (37.92 mi)
- La Pointe Hotels (8.65 mi)
- Iron River Hotels (27.78 mi)
- Cornucopia Hotels (18.3 mi)
- Great Lakes Hotels (364.73 mi)
- Port Wing Hotels (27.16 mi)
- Herbster Hotels (23.27 mi)
- Mellen Hotels (24.55 mi)
- Upson Hotels (28.66 mi)
- Red Cliff Hotels (13.77 mi)
- Saxon Hotels (23.19 mi)
- Mason Hotels (18.69 mi)
- Northwest Wisconsin Hotels (81.47 mi)
- Marengo Hotels (16.39 mi)