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Ashland Vacations

Pack those stellar shades. We have Ashland vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Ashland – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Ashland vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Ashland

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Ashland vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Ashland well.

Top Hotel Deals

See all 56 Hotels in Ashland
Best Western The Hotel Chequamegon

Best Western The Hotel Chequamegon

101 Lake Shore Dr W, Ashland
    3.0 out of 5.0
     
     

    Situated on a lake, this hotel is 0.4 mi (0.6 km) from Ashland Historical Museum and 2.4 mi (3.9 km) from Chequamegon Bay Golf Course. Northern Great Lakes Visitor ...

    Best Western The Hotel Chequamegon$130

    Best Western The Hotel Chequamegon$130
    Super 8 by Wyndham Ashland

    Super 8 by Wyndham Ashland

    1610 Lake Shore Dr W, Ashland
      2.0 out of 5.0
       
       

      Situated in Ashland, this hotel is 0.8 mi (1.3 km) from Ashland Historical Museum and 1.4 mi (2.2 km) from Chequamegon Bay Golf Course. Northern Great Lakes ...

      Super 8 by Wyndham Ashland$95

      Super 8 by Wyndham Ashland$95
      Quality Inn

      Quality Inn

      30600 Us Highway 2, Ashland
        3.0 out of 5.0
         
         

        Located in the heart of Ashland, this motel is within 3 mi (5 km) of Northern Great Lakes Visitor Center, Ashland Historical Museum, and Chequamegon Bay Golf ...

        Quality Inn$85

        Quality Inn$85
        AmericInn by Wyndham Ashland

        AmericInn by Wyndham Ashland

        3009 Lakeshore Drive East, Ashland
          2.5 out of 5.0
           
           

          Situated in Ashland, this hotel is 2.7 mi (4.3 km) from Ashland Historical Museum and within 9 mi (15 km) of Chequamegon Bay Golf Course and Northern Great Lakes ...

          AmericInn by Wyndham Ashland$130

          AmericInn by Wyndham Ashland$130
          Second Wind Country Inn

          Second Wind Country Inn

          30475 Carlson Rd, Ashland
            3.0 out of 5.0
             
             

            Situated in a rural location, this bed & breakfast is 2.5 mi (4.1 km) from Chequamegon Bay Golf Course and within 6 mi (10 km) of Ashland Historical Museum and ...

            Mission Springs Resort

            Mission Springs Resort

            30175 Mission Springs Road, Ashland
              3.0 out of 5.0
               
               

              This Ashland cottage is on the beach, 2.1 mi (3.4 km) from Northern Great Lakes Visitor Center, and within 6 mi (10 km) of Chequamegon Bay Golf Course and Ashland ...

              Mission Springs Lake House

              Mission Springs Lake House

              30190 Mission Springs Road, Ashland
                3.0 out of 5.0
                 
                 

                This Ashland cottage is on the beach, 2.1 mi (3.4 km) from Northern Great Lakes Visitor Center, and within 6 mi (10 km) of Chequamegon Bay Golf Course and Ashland ...

                The Washburn Inn - On the Lake

                The Washburn Inn - On the Lake

                123 Harbor View Drive, Washburn
                  2.5 out of 5.0
                   
                   

                  Situated on the waterfront, this hotel is 0.6 mi (1 km) from Bayfield County Courthouse and within 12 mi (20 km) of Northern Great Lakes Visitor Center and Mount ...

                  Days Inn by Wyndham Hurley

                  Days Inn by Wyndham Hurley

                  13355 N. US Hwy 51, Hurley
                    2.0 out of 5.0
                     
                     

                    Situated in Hurley, this hotel is within 2 mi (3 km) of Iron County Historical Society Museum, Old Depot Park Museum, and Historic Ironwood Theatre. Ironwood ...

                    Days Inn by Wyndham Hurley$79

                    Days Inn by Wyndham Hurley$79
                    Lucy's Place

                    Lucy's Place

                    120 South Sixth Street, Bayfield
                       
                       

                      Situated on a lake, this bed & breakfast is within a 10-minute walk of Apostle Islands Marina, Bayfield Heritage Museum, and Christ Episcopal Church. Bayfield ...

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.