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Bailey's Bay Vacations

Pack those stellar shades. We have Bailey's Bay 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 Bailey's Bay – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Bailey's Bay 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 Bailey's Bay

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 Bailey's Bay 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 Bailey's Bay well.

Top Hotel Deals

See all 60 Hotels in Bailey's Bay
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$258

    Coco Reef Bermuda$258
    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$359

      Grotto Bay Beach Resort$359
      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$351

        Fairmont Southampton$351
        The Loren at Pink Beach

        The Loren at Pink Beach

        116 South Shore Rd, Smith's
          4.5 out of 5.0
           
           

          Nestled on the beach, this Smith's hotel is within a 10-minute walk of John Smith's Beach and Devil's Hole Aquarium. Mid Ocean Golf Club and Tucker's Point Golf ...

          The Reefs Hotel and Club

          The Reefs Hotel and Club

          56 South Shore Road, Southampton
            4.0 out of 5.0
             
             

            Nestled on the beach, this Southampton hotel is within a 15-minute walk of Church Bay and Gibb's Hill Lighthouse. Horseshoe Bay is 1.4 mi (2.3 km) away.

            The Reefs Hotel and Club$326

            The Reefs Hotel and Club$326
            Pompano Beach Club

            Pompano Beach Club

            36 Pompano Beach Road, Southampton
              4.0 out of 5.0
               
               

              Nestled on the beach, this Southampton resort is within 2 mi (3 km) of Port Royal Golf Course, West Whale Bay, and Somerset Bridge. Church Bay and Seymour's ...

              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, ...

                Hamilton Princess & Beach Club - a Fairmont Managed Hotel$424

                Hamilton Princess & Beach Club - a Fairmont Managed Hotel$424
                Royal Palms Hotel

                Royal Palms Hotel

                24 Rosemont Avenue, Pembroke
                  3.5 out of 5.0
                   
                   

                  Situated just a short distance from Hamilton and surrounded by subtropical gardens, Royal Palms Hotel is within easy reach of both Hamilton Ferry Dock and Bermuda ...

                  The St. George's Club Bermuda

                  The St. George's Club Bermuda

                  6 Rose Hill, St. George's
                    3.0 out of 5.0
                     
                     

                    Situated near the beach, this hotel is within a 5-minute walk of Tucker House Museum, St. Peter's Church, and Bermuda National Trust Museum. Old Rectory and ...

                    Fourways Inn

                    Fourways Inn

                    1, Middle Road, Paget
                      3.0 out of 5.0
                       
                       

                      Situated near the beach, this cottage is 0.3 mi (0.5 km) from Darrell's Wharf and 2.9 mi (4.7 km) from Horseshoe Bay. Belmont Hills Golf Club and Warwick Pond ...

                      Top Flight Deals

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