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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 179 Properties in Ashland
Quality Inn & Suites

Quality Inn & Suites

107 N Carter Road, Ashland
    2.5 out of 5.0
     
     

    Situated in Ashland, this hotel is within 1 mi (2 km) of Randolph-Macon College and Ashland/Hanover Visitor's Center. James River Cellars Winery and Hanover ...

    Quality Inn & Suites$85

    Quality Inn & Suites$85
    Country Inn & Suites by Radisson, Ashland - Hanover, VA

    Country Inn & Suites by Radisson, Ashland - Hanover, VA

    11600 Lakeridge Pkwy, Ashland
      3.0 out of 5.0
       
       

      Situated in the business district, this hotel is 1.9 mi (3 km) from James River Cellars Winery and within 6 mi (10 km) of Randolph-Macon College and Ashland/Hanover ...

      Country Inn & Suites by Radisson, Ashland - Hanover, VA$87

      Country Inn & Suites by Radisson, Ashland - Hanover, VA$87
      Fairfield Inn & Suites by Marriott Richmond Ashland

      Fairfield Inn & Suites by Marriott Richmond Ashland

      11625 Lakeridge Parkway, Ashland
        2.5 out of 5.0
         
         

        Situated in the historical district, this hotel is 1.8 mi (2.9 km) from James River Cellars Winery and within 6 mi (10 km) of Randolph-Macon College and Ashland/Hanover ...

        Fairfield Inn & Suites by Marriott Richmond Ashland$119

        Fairfield Inn & Suites by Marriott Richmond Ashland$119
        Super 8 by Wyndham Ashland/Richmond

        Super 8 by Wyndham Ashland/Richmond

        806b England St, Ashland
          2.0 out of 5.0
           
           

          Situated in Ashland, this motel is within 1 mi (2 km) of Randolph-Macon College and Ashland/Hanover Visitor's Center. James River Cellars Winery and Hanover ...

          Super 8 by Wyndham Ashland/Richmond$55

          Super 8 by Wyndham Ashland/Richmond$55
          Hampton Inn by Hilton Richmond-North/Ashland

          Hampton Inn by Hilton Richmond-North/Ashland

          705 England St, Ashland
            2.5 out of 5.0
             
             

            Situated in the suburbs, this hotel is 0.6 mi (1 km) from Randolph-Macon College and within 9 mi (15 km) of Kings Dominion and Meadow Event Park.

            Hampton Inn by Hilton Richmond-North/Ashland$101

            Hampton Inn by Hilton Richmond-North/Ashland$101
            Days Inn by Wyndham Ashland

            Days Inn by Wyndham Ashland

            806 England St, Ashland
              2.0 out of 5.0
               
               

              Situated in Ashland, this motel is within 1 mi (2 km) of Randolph-Macon College and Ashland/Hanover Visitor's Center. James River Cellars Winery and Hanover ...

              Days Inn by Wyndham Ashland$60

              Days Inn by Wyndham Ashland$60
              Holiday Inn Express Hotel & Suites Richmond North Ashland

              Holiday Inn Express Hotel & Suites Richmond North Ashland

              107 Carter Rd S, Ashland
                2.5 out of 5.0
                 
                 

                Situated in Ashland, this hotel is within 1 mi (2 km) of Randolph-Macon College and Ashland/Hanover Visitor's Center. James River Cellars Winery and Hanover ...

                Holiday Inn Express Hotel & Suites Richmond North Ashland$100

                Holiday Inn Express Hotel & Suites Richmond North Ashland$100
                Motel 6 Ashland

                Motel 6 Ashland

                101 N Cottage Green Dr, Ashland
                  2.0 out of 5.0
                   
                   

                  Situated in Ashland, this motel is within 1 mi (2 km) of Randolph-Macon College and Ashland/Hanover Visitor's Center. James River Cellars Winery and Hanover ...

                  Motel 6 Ashland$50

                  Motel 6 Ashland$50
                  Sleep Inn & Suites Ashland - Richmond North

                  Sleep Inn & Suites Ashland - Richmond North

                  80 S Cottage Green Dr, Ashland
                    2.5 out of 5.0
                     
                     

                    Located in the heart of Ashland, this hotel is within 1 mi (2 km) of Randolph-Macon College and Ashland/Hanover Visitor's Center. James River Cellars Winery ...

                    Sleep Inn & Suites Ashland - Richmond North$84

                    Sleep Inn & Suites Ashland - Richmond North$84
                    The Tinder Guest House

                    The Tinder Guest House

                    106 B South Railroad Avenue, Ashland
                      3.0 out of 5.0
                       
                       

                      Located in the heart of Ashland, this bed & breakfast is within a 5-minute walk of Ashland/Hanover Visitor's Center and Randolph-Macon College. James River Cellars ...

                      The Tinder Guest House$250

                      The Tinder Guest House$250

                      Top Flight Deals

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