Ashland County Holidays

Photo by Anthony Ball

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now

Top hotels in Ashland County

Cobblestone Inn & Suites - Ashland

Cobblestone Inn & Suites - Ashland

2.5 out of 5
818 Main Street W. Ashland WI
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (757 reviews)
Nice hotel.very clean and nice staff.

Reviewed on 26 Feb, 2026

Get rates
Cobblestone Inn & Suites - Ashland
AmericInn by Wyndham Ashland

AmericInn by Wyndham Ashland

2.5 out of 5
3009 Lakeshore Drive East Ashland WI
Fully refundableReserve now, pay when you stay
The price is S$167 per night from 8 Mar to 9 Mar
S$167
8 Mar - 9 Mar
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Room was clean, night desk staff was courteous and helpful, friendly. Breakfast was good and room was clean,well maintained for breakfast.Used the pool, hot tub and sauna--the hot tub needs regular cleaning, water had debri in it so I got out as soon as I noticed.

Reviewed on 24 Feb, 2026

AmericInn by Wyndham Ashland
Best Western The Hotel Chequamegon

Best Western The Hotel Chequamegon

3 out of 5
101 Lake Shore Dr W Ashland WI
Fully refundableReserve now, pay when you stay
The price is S$197 per night from 1 Mar to 2 Mar
S$197
1 Mar - 2 Mar
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
I loved this place, perfect combination of modern and old charm. The room was huge and comfortable with a great view of frozen Lake Superior.

Reviewed on 25 Feb, 2026

Best Western The Hotel Chequamegon
See all 1,056 properties in Ashland County
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.

Frequently asked questions

How much does an Ashland County holiday package cost?
Our Ashland County holiday packages, which begin at just , are the perfect way to save. Pick and choose your favourite hotels, flights and rental car to create your dream trip.
How do I get a cheap travel package to Ashland County?
Bundle your bookings with Expedia to save big bucks on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Ashland County holiday package can be tailored exactly to suit your travel style. With all those extra dollars, why not include one or more fun tours and activities? It's an easy way to unlock even more discounts. Your dream holiday in Ashland County is much closer than you thought!
How far in advance should I book my Ashland County holiday?
It all depends on the airline, but you can usually browse through international airfares on Expedia up to 12 months in advance. While it's generally a good idea to book ahead of time, lucky customers will occasionally score a cheaper ticket just weeks before departure dates.
What does an Expedia Ashland County travel package include?
Expedia has all you need to plan your Ashland County getaway, but how you structure your package is your choice. Pick from any combination of flights, rental cars and hotels. Looking for some activities or tours to keep you on the go? Once you've made your booking, you can add them on too. Whatever your style, there's a package deal to meet your needs.
What should I know before booking an Ashland County travel package?
So many places to travel to, so many things to see and do. With a package, you can cross more of them off your list. Combine your hotels, flights and rental cars and get set to save.
Can I choose my airline with an Ashland County Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our holiday packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Ashland County holiday package?
You can. We totally understand that even the best-laid plans can fail, so we're here to help if you need to make changes to your Ashland County holiday package. You may be able to cancel or amend your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.