Win a Nantucket Five-Star Weekend Getaway & Premium Prize Packages (70 Winners)

Open For:14 Days

Entry Type : Multiple

Prize Type : Trip

Total ARV : $30.6K+

United States

Start Date: July 1, 2026 End Date: July 31, 2026 Draw Date: August 1, 2026 Posted Date: July 17, 2026

Difficulty Level : Very Easy ( 1 out of 5 )

Experience an unforgettable luxury escape by entering the On The Rocks Five Star Weekend Sweepstakes for your chance to win a dream trip to beautiful Nantucket or one of dozens of premium prize packages. From luxury accommodations and exclusive experiences to gift cards and more, this sweepstakes offers exciting rewards for lucky winners. Don't miss your opportunity to enter before time runs out!

Limit:

One standard entry per person and email address, plus one optional bonus entry by opting into On The Rocks marketing communications, for a maximum of two (2) total entries per person/email.
Must be 21 years of age or older and a legal resident of the 50 United States or the District of Columbia.

How to Enter

Online Entry Method

Visit fivestar.otrcocktails.com during the promotion period. Verify your age by entering your birthdate, then complete the registration form with your name, physical address, date of birth, email address, and phone number. Accept the Official Rules and Privacy Policy, then submit your entry.

Bonus Entry Method

During registration, if available, choose to receive marketing communications from On The Rocks to earn additional bonus entry.

Random Drawing

A random drawing will be held on 08/01/2026. One Grand Prize winner will be selected first, followed by 69 Secondary Prize winners. Winners will be notified by email and must respond within 48 hours or an alternate winner may be selected.