Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Shelter Island Vacations

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

Hotwire can help you find your travel bliss with Shelter Island 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 Shelter Island

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 Shelter Island 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 Shelter Island well.

Shelter Island Flight + Hotel packages

Top Hotel Deals

See all 1,514 Properties in Shelter Island
Best Western Plus Island Palms Hotel & Marina

Best Western Plus Island Palms Hotel & Marina

2051 Shelter Island Dr, San Diego
    3.0 out of 5.0
     
     

    This hotel is set on Shelter Island, surrounded by San Diego Bay and a private marina; Old Town is 5 miles away, and downtown San Diego is within 6 miles.

    Best Western Plus Island Palms Hotel & Marina$167

    Best Western Plus Island Palms Hotel & Marina$167
    Kona Kai Resort & Spa, A Noble House Resort

    Kona Kai Resort & Spa, A Noble House Resort

    1551 Shelter Island Drive, San Diego
      4.0 out of 5.0
       
       

      Situated at the tip of Shelter Island, this 8-acre resort is 6 miles (9.7 kilometers) from SeaWorld and Seaport Village; historic Old Town and downtown San Diego ...

      Bay Club Hotel & Marina

      Bay Club Hotel & Marina

      2131 Shelter Island Dr, San Diego
        3.5 out of 5.0
         
         

        3 miles from the San Diego Airport, Bay Club Hotel & Marina is 5 miles from SeaWorld, the cruise-ship terminal, Seaport Village shops and restaurants, and the ...

        Bay Club Hotel & Marina$161

        Bay Club Hotel & Marina$161
        Humphreys Half Moon Inn

        Humphreys Half Moon Inn

        2303 Shelter Island Dr, San Diego
          3.5 out of 5.0
           
           

          Humphreys Half Moon Inn sits on 14 acres adjacent to a yacht-filled marina overlooking San Diego Bay.

          Humphreys Half Moon Inn$179

          Humphreys Half Moon Inn$179
          Wyndham Garden San Diego Near SeaWorld

          Wyndham Garden San Diego Near SeaWorld

          3737 Sports Arena Blvd, San Diego
            3.0 out of 5.0
             
             

            Located in San Diego, this family-friendly hotel is 1 mile from SeaWorld Adventure Park and 2 miles from Mission Beach. Belmont Park is 2.4 miles away.

            Wyndham Garden San Diego Near SeaWorld$125

            Wyndham Garden San Diego Near SeaWorld$125
            Town and Country San Diego

            Town and Country San Diego

            500 Hotel Circle North, San Diego
              3.5 out of 5.0
               
               

              Comprising 32 acres, this resort and conference center is next to the 27-hole Riverwalk Golf Club; Old Town, Balboa Park, SeaWorld San Diego, and the world famous ...

              Town and Country San Diego$110

              Town and Country San Diego$110
              Hard Rock Hotel San Diego

              Hard Rock Hotel San Diego

              207 5th Ave, San Diego
                4.0 out of 5.0
                 
                 

                The Hard Rock Hotel is in the center of San Diego's bustling Gaslamp Quarter, with restaurants, bars, and nightlife. The San Diego Convention Center is across ...

                Hard Rock Hotel San Diego$143

                Hard Rock Hotel San Diego$143
                Best Western Seven Seas

                Best Western Seven Seas

                411 Hotel Circle South, San Diego
                  3.0 out of 5.0
                   
                   

                  Adjacent to I-8, this budget-friendly hotel is within 6 miles of 2 sports stadiums, the Gaslamp Quarter, the convention center, the San Diego Zoo, SeaWorld, ...

                  Best Western Seven Seas$113

                  Best Western Seven Seas$113
                  Ramada Hotel & Conference Center by Wyndham San Diego North

                  Ramada Hotel & Conference Center by Wyndham San Diego North

                  5550 Kearny Mesa Rd, San Diego
                    3.5 out of 5.0
                     
                     

                    Surrounded by palm trees, this hotel is situated on 5 acres of land, 9 miles from La Jolla beaches, 8 miles from the San Diego Zoo, and about 5 miles from the ...

                    Ramada Hotel & Conference Center by Wyndham San Diego North$102

                    Ramada Hotel & Conference Center by Wyndham San Diego North$102
                    The Sofia Hotel

                    The Sofia Hotel

                    150 W Broadway, San Diego
                      3.5 out of 5.0
                       
                       

                      In the heart of downtown San Diego, this historic boutique hotel is 2 blocks from Horton Plaza, 4 blocks from the Gaslamp Quarter, and 6 blocks from the San ...

                      The Sofia Hotel$125

                      The Sofia Hotel$125

                      Top Flight Deals

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