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Southampton Vacations

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

Hotwire can help you find your travel bliss with Southampton 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 Southampton

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 Southampton 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 Southampton well.

Southampton Flight + Hotel packages

Top Hotel Deals

See all 57 Properties in Southampton
Fairmont Southampton

Fairmont Southampton

101 South Shore Road, Southampton
    4.5 out of 5.0
     
     

    Expansive grounds, a private pink-sand beach, turquoise cove, and panoramic ocean views provide the setting for families and couples. This Bermuda resort is ...

    Fairmont Southampton$485

    Fairmont Southampton$485
    Pompano Beach Club

    Pompano Beach Club

    36 Pompano Beach Road, Southampton
      4.0 out of 5.0
       
       

      Located in Southampton, this beachfront resort is next to a golf course and within 1 mi (2 km) of Port Royal Golf Course and Rockaway Ferry. Robinson's Marina ...

      Hamilton Princess & Beach Club - a Fairmont Managed Hotel

      Hamilton Princess & Beach Club - a Fairmont Managed Hotel

      76 Pitts Bay Road, Pembroke
        4.5 out of 5.0
         
         

        Located in the heart of Hamilton with magnificent harbor views, Hamilton Princess & Beach Club- a Fairmont Managed Hotel offers pure luxury directly on the waterfront, ...

        Grotto Bay Beach Resort

        Grotto Bay Beach Resort

        11 Blue Hole Hill, Hamilton Parish
          3.5 out of 5.0
           
           

          This beachfront resort winds through 21 acres of flowering gardens and tropical forests along the ocean. The hotel is located within one-half mile of Crystal ...

          Grotto Bay Beach Resort$449

          Grotto Bay Beach Resort$449
          Cambridge Beaches Resort & Spa

          Cambridge Beaches Resort & Spa

          30 Kings Point Road Somerset, Sandys
            4.0 out of 5.0
             
             

            Set on a Bermuda peninsula edged by the ocean and beautiful bays, this tranquil cottage colony features 4 private beaches and a renowned European-style spa.

            Cambridge Beaches Resort & Spa$378

            Cambridge Beaches Resort & Spa$378
            Coco Reef Bermuda

            Coco Reef Bermuda

            3 Stonington Circle, Paget
              3.5 out of 5.0
               
               

              This beachfront resort is situated in extensive, manicured gardens on the breathtaking south shore of Bermuda. Coco Reef is on Elbow Beach yet only 5 minutes ...

              Coco Reef Bermuda$250

              Coco Reef Bermuda$250
              Elbow Beach

              Elbow Beach

              60 South Shore Road, Paget
                4.0 out of 5.0
                 
                 

                Surrounded by 50 acres of lush, landscaped gardens, this beachfront resort is located along a private stretch of Bermuda's south shore. Downtown Hamilton and ...

                Elbow Beach$675

                Elbow Beach$675
                The Oxford House

                The Oxford House

                20 Woodbourne Avenue, Hamilton
                  3.5 out of 5.0
                   
                   

                  Situated in the business district, this bed & breakfast is within a 5-minute walk of Hamilton Ferry Dock and Albuoy's Point Park. The Birdcage and Bermuda Historical ...

                  The Oxford House$290

                  The Oxford House$290
                  Inverurie Executive Suites

                  Inverurie Executive Suites

                  1 Harbour Road, Paget
                    3.5 out of 5.0
                     
                     

                    Situated by the sea, this hotel is 0.1 mi (0.1 km) from Darrell's Wharf and 2.8 mi (4.5 km) from Horseshoe Bay. Belmont Hills Golf Club and Warwick Pond are ...

                    Rosemont Guest Suites

                    Rosemont Guest Suites

                    41 Rosemont Avenue, Pembroke
                      3.5 out of 5.0
                       
                       

                      Situated in Pembroke, this apartment building is within a 10-minute walk of Hamilton Ferry Dock, Albuoy's Point Park, and The Birdcage. Bermuda Historical Society ...

                      Rosemont Guest Suites$274

                      Rosemont Guest Suites$274

                      Top Flight Deals

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