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Chester Vacations

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

Hotwire can help you find your travel bliss with Chester 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 Chester

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 Chester 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 Chester well.

Chester Flight + Hotel packages

Top Hotel Deals

See all 55 Hotels in Chester
Rum Runner Inn

Rum Runner Inn

66 Montague Street, Lunenburg
    4.0 out of 5.0
     
     

    Situated by the ocean, this hotel is steps from Bluenose II, Lunenburg Art Gallery, and Fisheries Museum of the Atlantic. Knaut Rhuland House Museum and St John's ...

    Oak Island Resort & Conference Centre

    Oak Island Resort & Conference Centre

    36 Treasure Drive, Western Shore
      3.5 out of 5.0
       
       

      Situated in Western Shore, this spa resort is within 9 mi (15 km) of Mahone Bay Settlers Museum, Mahone Bay Swimming Pool, and Lordly House Museum. St. Stephen's ...

      Oak Island Resort & Conference Centre$105

      Oak Island Resort & Conference Centre$105
      Smugglers Cove Inn

      Smugglers Cove Inn

      139 Montague St, Lunenburg
        4.0 out of 5.0
         
         

        Situated in a rural location, this hotel is steps from Knaut Rhuland House Museum, Gallery @ theLinc, and Lunenburg Opera House. Fisheries Museum of the Atlantic ...

        Best Western Plus Bridgewater Hotel & Convention Centre

        Best Western Plus Bridgewater Hotel & Convention Centre

        527 Highway 10 Exit 12, Bridgewater
          3.5 out of 5.0
           
           

          Situated in Bridgewater, this hotel is within 3 mi (5 km) of Cookville Provincial Park, Osprey Ridge Golf Course, and Bridgewater Mall. Bridgewater Memorial ...

          Best Western Plus Bridgewater Hotel & Convention Centre$89

          Best Western Plus Bridgewater Hotel & Convention Centre$89
          Mariner King Inn

          Mariner King Inn

          15 King Street, Lunenburg
            4.0 out of 5.0
             
             

            Located in the heart of Lunenburg, this historic bed & breakfast is steps from Lunenburg Opera House, Knaut Rhuland House Museum, and Gallery @ theLinc. Lunenburg ...

            Days Inn & Conference Center by Wyndham Bridgewater

            Days Inn & Conference Center by Wyndham Bridgewater

            50 North Street, Bridgewater
              2.5 out of 5.0
               
               

              Located in the heart of Bridgewater, this hotel is within 1 mi (2 km) of Bridgewater Mall and Bridgewater Memorial Arena. Wile Carding Mill Museum and Kinsmen ...

              Days Inn & Conference Center by Wyndham Bridgewater$75

              Days Inn & Conference Center by Wyndham Bridgewater$75
              Atlantic View Motel and Cottages

              Atlantic View Motel and Cottages

              230 Mason's Beach Road, RR#2, Lunenburg
                3.0 out of 5.0
                 
                 

                Situated on the waterfront, this motel is within 1 mi (2 km) of Bluenose Golf Club, Pearl Theatre, and Bluenose II. Fisheries Museum of the Atlantic and St John's ...

                Anchorage House and Cottages

                Anchorage House and Cottages

                56 Shore Club Rd, Hubbards
                  3.0 out of 5.0
                   
                   

                  Situated in Hubbards, this cottage is within 1 mi (2 km) of Shore Club Dance Hall, Hubbards Beach, and Hubbards Barn and Community Park. Hooked Rug Museum of ...

                  Fairmont House Bed & Breakfast

                  Fairmont House Bed & Breakfast

                  654 Main Street, Mahone Bay
                    3.0 out of 5.0
                     
                     

                    Situated in Mahone Bay, this bed & breakfast is within a 15-minute walk of Mahone Bay Settlers Museum and Mahone Bay Swimming Pool. Bluenose II and Fisheries ...

                    The Dockside Inn & Restaurant

                    The Dockside Inn & Restaurant

                    84 Montague Street, Lunenburg
                      3.0 out of 5.0
                       
                       

                      Situated in Lunenburg, this inn is steps from Lunenburg Art Gallery, Fisheries Museum of the Atlantic, and Bluenose II. Knaut Rhuland House Museum and St John's ...

                      Top Flight Deals

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