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Gloucester Vacations

Pack those stellar shades. We have Gloucester 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 Gloucester – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Gloucester 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 Gloucester

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 Gloucester 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 Gloucester well.

Top Hotel Deals

See all 191 Properties in Gloucester
Quality Inn Gloucester

Quality Inn Gloucester

6639 Forest Hill Ave, Gloucester
    2.5 out of 5.0
     
     

    Located in the heart of Gloucester, this hotel is within 20 mi (32 km) of Yorktown Beach, Lee Hall Mansion, and Yorktown Victory Center. Colonial National Historical ...

    Quality Inn Gloucester$85

    Quality Inn Gloucester$85
    Hampton Inn Gloucester

    Hampton Inn Gloucester

    6638 Forest Hill Ave, Gloucester
      2.5 out of 5.0
       
       

      Situated in Gloucester, this hotel is within 20 mi (32 km) of Yorktown Beach, Lee Hall Mansion, and Yorktown Victory Center. Colonial National Historical Park ...

      Hampton Inn Gloucester$109

      Hampton Inn Gloucester$109
      Chesapeake Bay RV Resort Thousand Trails - Campground

      Chesapeake Bay RV Resort Thousand Trails - Campground

      12014 Trails Lane, Gloucester
        2.0 out of 5.0
         
         

        Set in Gloucester, this family-friendly campground is 8.3 mi (13.3 km) from Middlesex County Museum and 11.7 mi (18.8 km) from Gloucester Museum of History. ...

        Days Inn by Wyndham Williamsburg Historic Area

        Days Inn by Wyndham Williamsburg Historic Area

        706 Bypass Road, Williamsburg
          2.5 out of 5.0
           
           

          Situated in the historical district, this motel is within 1 mi (2 km) of Colonial Williamsburg Visitor Center and Colonial Williamsburg. Governor's Palace is ...

          Days Inn by Wyndham Williamsburg Historic Area$59

          Days Inn by Wyndham Williamsburg Historic Area$59
          Woodlands Hotel & Suites - A Colonial Williamsburg Hotel

          Woodlands Hotel & Suites - A Colonial Williamsburg Hotel

          105 Visitors Center Dr, Williamsburg
            3.0 out of 5.0
             
             

            This family-friendly Williamsburg hotel is located in the historical district, within 1 mi (2 km) of Colonial Williamsburg Visitor Center and Merchants Square. ...

            Woodlands Hotel & Suites - A Colonial Williamsburg Hotel$139

            Woodlands Hotel & Suites - A Colonial Williamsburg Hotel$139
            Country Inn & Suites by Radisson, Williamsburg Historic Area, VA

            Country Inn & Suites by Radisson, Williamsburg Historic Area, VA

            400 Bypass Rd, Williamsburg
              3.0 out of 5.0
               
               

              Situated in Williamsburg, this hotel is within 2 mi (3 km) of Ripley's Believe It or Not!, Colonial Williamsburg, and Governor's Palace. Colonial Williamsburg ...

              Country Inn & Suites by Radisson, Williamsburg Historic Area, VA$94

              Country Inn & Suites by Radisson, Williamsburg Historic Area, VA$94
              The Historic Powhatan Resort by Diamond Resorts

              The Historic Powhatan Resort by Diamond Resorts

              3601 Ironbound Rd, Williamsburg
                3.5 out of 5.0
                 
                 

                On a former colonial plantation, this 256-acre property is 3 miles from Colonial Williamsburg and 12 miles from Busch Gardens.

                The Historic Powhatan Resort by Diamond Resorts$140

                The Historic Powhatan Resort by Diamond Resorts$140
                Fort Magruder Hotel and Conference Center

                Fort Magruder Hotel and Conference Center

                6945 Pocahontas Trail, Williamsburg
                  3.5 out of 5.0
                   
                   

                  Situated in the historical district, this hotel is within 1 mi (2 km) of Quarterpath Park and Colonial Williamsburg. Busch Gardens Williamsburg and Governor's ...

                  Fort Magruder Hotel and Conference Center$79

                  Fort Magruder Hotel and Conference Center$79
                  Park Inn by Radisson Williamsburg Historic

                  Park Inn by Radisson Williamsburg Historic

                  2007 Richmond Rd, Williamsburg
                    2.0 out of 5.0
                     
                     

                    Situated in Williamsburg, this hotel is 0.2 mi (0.3 km) from Ripley's Believe It or Not! and within 3 mi (5 km) of Colonial Williamsburg and Governor's Palace. ...

                    Park Inn by Radisson Williamsburg Historic$61

                    Park Inn by Radisson Williamsburg Historic$61
                    Point Plaza Suites at City Center

                    Point Plaza Suites at City Center

                    950 J. Clyde Morris Blvd., Newport News
                      3.0 out of 5.0
                       
                       

                      Located in the heart of Newport News, this hotel is within 3 mi (5 km) of Virginia Living Museum, Hampton Roads Iceplex, and Riverside Medical Center. Mariner's ...

                      Point Plaza Suites at City Center$44

                      Point Plaza Suites at City Center$44

                      Top Flight Deals

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