Mexico, Aruba, the Dominican Republic, US Virgin Islands, the Bahamas, Jamaica, Barbados - these places welcome visitors all year round. All of these countries actively promote their tourism benefits, and tourists are very loved and appreciated there.
There are always many good deals. For reference, a 5-star hotel in Cancun, Mexico for a week with the flight from New York, will cost estimated $3,000 for two.
Please check in advance whether you need a visa to that country, and make sure that you have a multiple-entry US visa and will be able to return to New York, if you fly back home from there.