Chequamegon Bay Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Chequamegon Bay vacation package deals
Price found within the past 48 hours. Click for updated prices.
2.0-star property
Super 8 by Wyndham Ashland
8/10 Very Good! (1,022 reviews)
Oct 23 - Oct 26
3 night stay
Chicago (ORD) to Duluth (DLH)
Denver Air Connection • Roundtrip • Coach
per person
found 1 day ago
I couldn’t get the tv to work and as soon as I called the front desk someone came up very fast and showed me how to work it. Everyone was very polite and the room was neat and clean.
Reviewed on Jul 14, 2025
2.5-star property
AmericInn by Wyndham Ashland
7.8/10 Good! (1,008 reviews)
Oct 23 - Oct 26
3 night stay
Chicago (ORD) to Duluth (DLH)
Denver Air Connection • Roundtrip • Coach
per person
found 1 day ago
Nice, clean property. Great breakfast selection. Not packed and able to get parking by room.
Reviewed on Jan 28, 2025
3.0-star property
Mission Springs Resort
9.4/10 Exceptional! (57 reviews)
Oct 23 - Oct 26
3 night stay
Chicago (ORD) to Duluth (DLH)
Denver Air Connection • Roundtrip • Coach
per person
found 1 day ago
I was super impressed with how clean the cabin was! We did not spend much time at the cabin as we spent most days exploring the area. Never saw host, but they reached out several times to make sure we didnt need anything and also gave us dinner recommendations.
Reviewed on May 16, 2021
2.5-star property
Quality Inn Ashland - Lake Superior
8.8/10 Excellent! (829 reviews)
Sep 16 - Sep 20
4 night stay
Syracuse (SYR) to Duluth (DLH)
United • Non-stop roundtrip • Coach
per person
found 21 hours ago
Great place to stay, have stayed on multiple occasions and will keep going back
Reviewed on Feb 12, 2024
2.5-star property
Cobblestone Inn & Suites - Ashland
9.4/10 Exceptional! (670 reviews)
Sep 16 - Sep 20
4 night stay
Syracuse (SYR) to Duluth (DLH)
United • Non-stop roundtrip • Coach
per person
found 21 hours ago
It was close to everything, we had a great time. The staff was very nice.
Reviewed on Apr 13, 2025
Top rated hotels for your Chequamegon Bay vacation package
The Washburn Inn - On the Lake
123 Harbor View Drive, Washburn, WI
2.55 mi from city center
$180 nightly
The price is $202 total per night
$202 total
Aug 10 - Aug 11
Total includes taxes and fees
Guests of The Washburn Inn - On the Lake enjoy access to free WiFi in public areas, a conference center, and coffee in a common area. Free parking is included with your stay. The 24-hour front desk has staff always at the ready. Other amenities at this golf hotel include express check-out, a terrace, and a banquet hall.
Pet friendly
Parking included
AmericInn by Wyndham Ashland
3009 Lakeshore Drive East, Ashland, WI
3.45 mi from city center
$149 nightly
The price is $167 total per night
$167 total
Sep 4 - Sep 5
Total includes taxes and fees
Guests of AmericInn by Wyndham Ashland have access to a private beach, 2 indoor pools, and a children's pool. Free parking is included with your stay. The front desk is staffed 24/7 to help with dry cleaning or laundry, and answer any questions about the accommodations. Other amenities at this beach hotel include a gym, a sauna, and free WiFi in public areas.
On private beach
Pool
Cobblestone Inn & Suites - Ashland
818 Main Street W., Ashland, WI
Free Cancellation
Reserve now, pay when you stay
5.55 mi from city center
$235 nightly
The price is $263 total per night
$263 total
Aug 10 - Aug 11
Total includes taxes and fees
Cobblestone Inn & Suites - Ashland features a gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a meeting room, laundry facilities, and a TV in a common area.
Pet friendly
Parking included
Don't see what you're looking for?
See all available properties in Chequamegon Bay
View all propertiesLowest 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.
